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CN1382152A - 新的a-500359衍生物 - Google Patents

新的a-500359衍生物 Download PDF

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CN1382152A
CN1382152A CN00814653A CN00814653A CN1382152A CN 1382152 A CN1382152 A CN 1382152A CN 00814653 A CN00814653 A CN 00814653A CN 00814653 A CN00814653 A CN 00814653A CN 1382152 A CN1382152 A CN 1382152A
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CN1176936C (zh
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穗户田仁
金子正胜
犬饲正俊
村松康范
宇津井幸男
大屋哲
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Daiichi Sankyo Co Ltd
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Abstract

本发明涉及通式(I)所示的化合物、其药理上可接受的盐;含有它们作为有效成分的用于预防或治疗细菌感染症的组合物;使用它们制造预防或治疗细菌感染症的药物的用途;以及使用药理有效量的它们对温血动物给药的细菌感染症的预防方法或治疗方法。式中,R1和R2表示可具有取代基的芳基、杂环基、烷基、链烯基,R3表示氢原子或羟基,X12表示氧原子、硫原子或可被取代的氮原子。

Description

新的A-500359衍生物
技术领域
本发明涉及具有优异抗菌活性的化合物(I)、其药理上可接受的衍生物和盐、含有它们作为有效成分的用于预防或治疗细菌感染症的组合物,使用它们制造预防或治疗细菌感染症的药物的用途,以及使用药理有效量的它们对温血动物给药的预防细菌感染症的方法或治疗细菌感染症的方法。
背景技术
作为细菌感染症的预防剂和治疗剂,以往使用各种β-内酰胺类,氨基配糖体类,喹诺酮羧酸,异烟肼类,利福平类等,但是最近对这些抗生素显示耐药性的感染菌渐渐增加,因此渴望与现有药物作用机理不同的药物。
卡普拉霉素是下面结构式所示的天然物,具有抗耐酸杆菌活性,虽然与现有的药物不显示交叉耐药性,但是其活性作为抗菌剂使用还不够充分(参见抗生素杂志:J.Antibiotics,29,(8),1047-1053(1986))。
本发明者,对产生微生物的卡普拉霉素类似物进行化学改性合成了各种化合物,对这些化合物的药理活性进行了多年深入地研究。其结果发现,通式(I)所示化合物、其药理上可接受的衍生物及其盐与现有的药物无交叉耐药性,具有优异的抗菌活性,作为细菌感染症的预防剂或治疗剂是有用的,并因此完成了本发明。
发明的公开
本发明包括,
通式(I)所示化合物、其药理上可接受的酯、醚或N-烷基衍生物或其药理上可接受的盐;
{式中
X1表示氧原子,硫原子或式-N(R4)-所示基团(式中,R4表示氢原子,碳原子数1~3的烷基,或与R1以及与它们连接的氮原子一起形成可含有氧原子或硫原子的3~7元环状氨基的基团),
X2表示氧原子,硫原子或式-N(R5)-所示基团(式中,R5表示氢原子,碳原子数1~3的烷基,或与R2以及与它们连接的氮原子一起形成可含有氧原子或硫原子的3~7元环状氨基的基团),
R1和R2可相同或不同,表示
(1)氢原子,
(2)可具有取代基的碳原子数6~10的芳基
[该取代基表示选自由卤原子,羟基,氨基(该氨基可被碳原子数1~16的烷基取代),硝基,氰基,羧基,碳原子1~4的烷氧羰基,氨基甲酰基,碳原子数1~10的亚烷基二氧基,碳原子数7~14的芳烷氧基,碳原子数1~16的烷基(该烷基可被卤原子取代),碳原子数2~16的链烯基,碳原子数1~16的烷氧基(该烷氧基可被卤原子取代),碳原子数1~16的烷硫基(该烷硫基可被卤原子取代),碳原子数6~10的芳基偶氮基,和含有1~4个氮原子,硫原子或氧原子的杂环基组成的取代基组A的基团],
(3)可具有取代基的含有1~4个氮原子、硫原子或氧原子的杂环基
[该取代基表示选自由氧代基,硫代氧代基,亚氨基,卤原子,羟基,氨基(该氨基可被碳原子数1~16的烷基取代),硝基,氰基,羧基,碳原子1~4的烷氧羰基,氨基甲酰基,碳原子数7~14的芳烷氧基,碳原子数1~16的烷基(该烷基可被卤原子取代),碳原子数1~16的链烯基,碳原子数1~16的烷氧基(该烷氧基可被卤原子取代),和碳原子数1~16的烷硫基(该烷硫基可被卤原子取代)组成的取代基组B的基团],
(4)具有1~3个相同或不同的可具有取代基的碳原子数6~10的芳基的碳原子数1~14的烷基
[该芳基部分的取代基为选自上述取代基组A的基团],
(5)具有1~3个相同或不同的可具有取代基的含有1~4个氮原子、硫原子或氧原子的杂环基的碳原子数1~14的烷基
[该杂环部分的取代基表示选自上述取代基组B的基团],
(6)可具有取代基的碳原子数1~22的烷基
[该取代基表示选自由卤原子,羟基,氨基,硝基,氰基,羧基,碳原子1~4的烷氧羰基,氨基甲酰基,碳原子数1~16的烷氧基(该烷氧基可被卤原子取代),和碳原子数1~16的烷硫基(该烷硫基可被卤原子取代)组成的取代基组C的基团],
(7)可具有取代基的碳原子数2~22的链烯基
[该取代基表示选自上述(2)或(3)的基团或选自取代基组C的基团]或
(8)式(a)所示基团
Figure A0081465300151
[式中,n表示1~20的整数,m表示0或2。],
R3表示氢原子或羟基。
条件是,X1和X2是式-NH-所示基团,R1是氢原子或式(II)、(III)、(IV)或(V)所示基团,R2是氢原子,R3是羟基的化合物,以及X1是氧原子,X2是式-NH-所示基团,R1是氢原子或甲基,R2是氢原子,R3是羟基的化合物除外。};
含有它们作为有效成分的用于预防或治疗细菌感染症的组合物;使用它们制造用于预防或治疗细菌感染症的药物的用途;以及使用药理有效量的它们对温血动物给药的预防细菌感染症的方法或治疗细菌感染症的方法。
上述通式(I)所示化合物中,
作为X1和X2中的R4和R5的“碳原子数1~3的烷基”,可列举例如,甲基,乙基,丙基或异丙基,优选甲基。
作为X1和X2中的R4和R5的“与R1(或R2)以及与它们连接的氮原子一起形成可含有氧原子或硫原子的3~7元环状氨基的基团”,可列举例如,氮杂环丙烷基,氮杂环丁烷基,吡咯烷基,哌啶基,吗啉基或硫代吗啉基等,优选是与R1(或R2)以及与它们连接的氮原子一起形成5或6元环状氨基的基团,更优选吡咯烷基。
作为X1中的R4,优选氢原子,碳原子数1~3的烷基或是与R1以及与它们连接的氮原子一起形成5或6元环状氨基的基团,更优选氢原子或碳原子数1~3的烷基,最优选氢原子。
作为X2中的R5,优选氢原子或碳原子数1~3的烷基,最优选氢原子。
作为X1全体,优选式-N(R4)-所示基团,更优选式-N(R4)-所示基团(式中,R4表示氢原子,碳原子数1~3的烷基,或与R1以及与它们连接的氮原子一起形成5或6元环状氨基的基团),更优选式-N(R4)-所示基团(式中,R4表示氢原子或碳原子数1~3的烷基),最优选式-NH-所示基团,
作为X2全体,优选式-N(R5)-所示基团,更优选式-N(R5)-所示基团(式中,R5表示氢原子或碳原子数1~3的烷基),最优选式-NH-所示基团。
在R1和R2的定义中,
作为“碳原子数6~10的芳基”,可列举例如,苯基,1-萘基,2-萘基等,优选苯基。
作为“含有1~4个氮原子、硫原子或氧原子的杂环基”,可列举呋喃基,噻吩基,吡咯基,吡唑基,咪唑基,噁唑基,异噁唑基,噻唑基,异噻唑基,三唑基,四唑基,噻二唑基,吡啶基,哒嗪基,嘧啶基,吡嗪基等5或6元芳族杂环基,以及四氢呋喃基,吗啉基,硫代吗啉基,吡咯烷基,吡咯啉基,咪唑烷基,吡唑烷基,吡唑啉基,哌啶基,哌嗪基,吡喃基等部分或完全还原型的5或6元杂环基。
另外,上述“5或6元芳族杂环基”或“部分或完全还原型5或6元杂环基”,可与苯等其它环基稠合,可列举例如,苯并呋喃基,苯并噻吩基,苯并咪唑基,异苯并呋喃基,苯并吡喃基,占吨基,吩噻噁基,吲哚嗪基,异吲哚基,吲哚基,吲唑基,嘌呤基,喹诺酊基,异喹啉基,喹啉基,2,3-二氮杂萘基,1,5-二氮杂萘基,喹喔啉基,喹唑啉基,咔唑基,α-咔啉基,吖啶基,二氢异吲哚基等基团。
这样的杂环基中,优选5或6元芳族杂环基或与苯环稠合的5或6元芳族杂环基,更优选呋喃基,噻吩基,吡啶基,噻唑基,噻二唑基或喹啉基。
“碳原子数1~22的烷基”是指碳原子数1~22的直链、支链或环状饱和烃基,可列举例如,甲基、乙基、丙基、异丙基、丁基、异丁基、仲丁基、叔丁基、戊基、异戊基、2-甲基丁基、新戊基、1-乙基丙基、己基、异己基、4-甲基戊基、3-甲基戊基、2-甲基戊基、1-甲基戊基、3,3-二甲基丁基、2,2-二甲基丁基、1,1-二甲基丁基、1,2-二甲基丁基、1,3-二甲基丁基、2,3-二甲基丁基、2-乙基丁基、庚基、1-甲基己基、2-甲基己基、3-甲基己基、4-甲基己基、5-甲基己基、1-丙基丁基、4,4-二甲基戊基、辛基、1-甲基庚基、2-甲基庚基、3-甲基庚基、4-甲基庚基、5-甲基庚基、6-甲基庚基、1-丙基戊基、2-乙基己基、5,5-二甲基己基、壬基、3-甲基辛基、4-甲基辛基、5-甲基辛基、6-甲基辛基、1-丙基己基、2-乙基庚基、6,6-二甲基庚基、癸基、1-甲基壬基、3-甲基壬基、8-甲基壬基、3-乙基辛基、3,7-二甲基辛基、7,7-二甲基辛基、十一烷基、4,8-二甲基壬基、十二烷基、十三烷基、十四烷基、十五烷基、3,7,11-三甲基十二烷基,十六烷基,4,8,12-三甲基十三烷基、1-甲基十五烷基、14-甲基十五烷基、13,13-二甲基十四烷基、十七烷基、15-甲基十六烷基、十八烷基、1-甲基十七烷基、十九烷基、二十烷基、3,7,11,15-四甲基十六烷基、二十一烷基、二十二烷基等直链或支链烷基;环丙基、环丁基、环戊基、环己基、甲基环己基、二甲基环己基、乙基环己基、丙基环己基、丁基环己基、叔丁基环己基、环庚基、环辛基、环壬基、环癸基、环十二烷基、降冰片烷基、金刚烷基等可具有支链或稠合环的3~12元环烷基;环丙基甲基、环丙基乙基、环丁基乙基、环丁基乙基、环戊基甲基、环戊基乙基、环己基甲基、环己基乙基、环己基丙基、环己基丁基、环己基己基等环烷基烷基,优选碳原子数1~18的直链或支链烷基或碳原子数5~12的环烷基。
“具有1~3个相同或不同的碳原子数6~10的芳基的碳原子数1~14的烷基”是指,被1~3个上述“碳原子数6~10的芳基”取代的“碳原子数1~14的烷基”。
“具有1~3个相同或不同的含有1~4个氮原子、硫原子或氧原子的杂环基的碳原子数1~14的烷基”是指,被1~3个上述“含有1~4个氮原子、硫原子或氧原子的杂环基”取代的“碳原子数1~14的烷基”。
“碳原子数2~22的链烯基”是指碳原子数2~22的具有1~3个双键的直链、支链或环状烃基,可列举例如,乙烯基、1-丙烯基、2-丙烯基、1-甲基-2-丙烯基、1-甲基-1-丙烯基、2-甲基-1-丙烯基、2-甲基-2-丙烯基、2-乙基-2-丙烯基、1-丁烯基、2-丁烯基、1-甲基-2-丁烯基、1-甲基-1-丁烯基、3-甲基-2-丁烯基、1-乙基-2-丁烯基、3-丁烯基、1-甲基-3-丁烯基、2-甲基-3-丁烯基、1-乙基-3-丁烯基、1-戊烯基、2-戊烯基、1-甲基-2-戊烯基、2-甲基-2-戊烯基、3-戊烯基、1-甲基-3-戊烯基、2-甲基-3-戊烯基、4-戊烯基、1-甲基-4-戊烯基、2-甲基-4-戊烯基、1-己烯基、2-己烯基、3-己烯基、4-己烯基、5-己烯基、庚烯基、辛烯基、癸烯基、十二碳烯基、十四碳烯基、十六碳烯基,顺-8-十七碳烯基、顺,顺-8、11-十七碳二烯基、顺,顺,顺-8、11、14-十七碳三烯基、顺-9-十八碳烯基、顺-10-十九碳烯基、顺-12-二十碳烯基等直链或支链链烯基;环戊烯基、甲基环戊烯基、环己烯基、甲基环己烯基、二甲基环己烯基、乙基环己烯基、丁基环己烯基、环庚烯基、环辛基希、环癸烯基、环十二碳烯基等可具有支链的任选具有取代基的环烯基;环戊烯甲基、环己烯甲基、环己烯乙基、环己烯丁基等环烯基烷基,优选碳原子数2~18的直链或支链链烯基或碳原子数5~8的环烯基烷基。
作为取代基组A、B和C中的“卤原子”,可列举例如,氟原子、氯原子、溴原子或碘原子,其中优选氟原子或氯原子。
取代基组A和B中的“氨基”可被碳原子数1~16的烷基取代,可列举例如,未取代的氨基、甲基氨基、乙基氨基、丙基氨基、丁基氨基、己基氨基、辛基氨基、癸基氨基、十二烷基氨基、十四烷基氨基、二甲基氨基、二乙基氨基、二丙基氨基、二丁基氨基。优选可被碳原子数1~6的烷基取代的氨基,更优选可被碳原子数1~3的烷基取代的氨基,特别优选氨基或二甲基氨基。
作为取代基组A中的“碳原子数1~10的亚烷基二氧基”,可列举例如,亚甲基二氧、1,1-亚乙基二氧、1,2-亚乙基二氧、1,1-亚丙基二氧、1,1-亚丁基二氧、1,1-亚己基二氧,1,1-亚辛基二氧、1,1-亚癸基二氧基,优选碳原子数1~3的亚烷基二氧,最优选亚甲基二氧基。
作为取代基组A、B和C中的“碳原子数1~4的烷氧羰基”,可列举例如,甲氧羰基、乙氧羰基、丙氧羰基、异丙氧羰基、丁氧羰基、异丁氧羰基、仲丁氧羰基、叔丁氧羰基等,优选甲氧羰基或乙氧羰基。
作为取代基组A和B中的“碳原子数7~14的芳烷氧基”,可列举例如,苯甲基氧基、1-苯乙基氧、2-苯乙基氧、3-苯丙基氧、2-苯基丙基氧、4-苯基丁基氧、1-萘基甲基氧、2-(1-萘基)乙基氧、3-(1-萘基)丙基氧、4-(1-萘基)丁基氧、2-萘基甲基氧、2-(2-萘基)乙基氧、3-(2-萘基)丙基氧、4-(2-萘基)丁基氧等,优选碳原子数7~10的苯基烷基氧基,更优选苄基氧或2-苯乙基氧基。
作为取代基组A和B中的“碳原子数1~16的烷基(该烷基可被卤原子取代)”,可列举例如,甲基、乙基、丙基、异丙基、丁基、异丁基、仲丁基、叔丁基、戊基、异戊基、2-甲基丁基、新戊基、1-乙基丙基、己基、异己基、4-甲基戊基、3-甲基戊基、2-甲基戊基、1-甲基戊基、3,3-二甲基丁基、2,2-二甲基丁基、1,1-二甲基丁基、1,2-二甲基丁基、1,3-二甲基丁基、2,3-二甲基丁基、2-乙基丁基、庚基、1-甲基己基、2-甲基己基、3-甲基己基、4-甲基己基、5-甲基己基、1-丙基丁基、4,4-二甲基戊基、辛基、1-甲基庚基、2-甲基庚基、3-甲基庚基、4-甲基庚基、5-甲基庚基、6-甲基庚基、1-丙基戊基、2-乙基己基、5,5-二甲基己基、壬基、3-甲基辛基、4-甲基辛基、5-甲基辛基、6-甲基辛基、1-丙基己基、2-乙基庚基、6,6-二甲基庚基、癸基、1-甲基壬基、3-甲基壬基、8-甲基壬基、3-乙基辛基、3,7-二甲基辛基、7,7-二甲基辛基、十一烷基、4,8-二甲基壬基、十二烷基、十三烷基、十四烷基、十五烷基、3,7,11-三甲基十二烷基,十六烷基,4,8,12-三甲基十三烷基、1-甲基十五烷基、14-甲基十五烷基、13,13-二甲基十四烷基、15-甲基十六烷基等直链或支链烷基;三氟甲基、2-氟乙基、2,2,2-三氟乙基、五氟乙基、七氟丙基、九氟丁基、十一氟戊基、十三氟己基、3-氟丙基、4-氟丁基、5-氟戊基、6-氟己基、氯甲基、二氯甲基、2-氯乙基、3-氯丙基、溴甲基、2-溴乙基等卤原子取代的直链或支链烷基,优选碳原子数1~16的烷基(该烷基可被氟原子或氯原子取代),更优选碳原子数1~16的烷基(该烷基可被氟原子取代)。
作为取代基组A和B中的“碳原子数1~16的链烯基”,可列举例如,乙烯基、1-丙烯基、2-丙烯基、1-甲基-2-丙烯基、1-甲基-1-丙烯基、2-甲基-1-丙烯基、2-甲基-2-丙烯基、2-乙基-2-丙烯基、1-丁烯基、2-丁烯基、1-甲基-2-丁烯基、1-甲基-1-丁烯基、3-甲基-2-丁烯基、1-乙基-2-丁烯基、3-丁烯基、1-甲基-3-丁烯基、2-甲基-3-丁烯基、1-乙基-3-丁烯基、1-戊烯基、2-戊烯基、1-甲基-2-戊烯基、2-甲基-2-戊烯基、3-戊烯基、1-甲基-3-戊烯基、2-甲基-3-戊烯基、4-戊烯基、1-甲基-4-戊烯基、2-甲基-4-戊烯基、1-己烯基、2-己烯基、3-己烯基、4-己烯基、5-己烯基、庚烯基、辛烯基、癸烯基、十二碳烯基、十四碳烯基、十六碳烯基等直链或支链链烯基,优选碳原子数2~10的链烯基。
作为取代基组A、B和C中的“碳原子数1~16的烷氧基(该烷氧基可被卤原子取代)”,可列举例如,甲氧基、乙氧基、丙氧基、异丙氧基、丁氧基、异丁氧基、仲丁氧基、叔丁氧基、戊氧基、异戊氧基、2-甲基丁氧基、新戊氧基、1-乙基丙氧基、己氧基、异己氧基、4-甲基戊氧基、3-甲基戊氧基、2-甲基戊氧基、1-甲基戊氧基、3,3-二甲基丁氧基、2,2-二甲基丁氧基、1,1-二甲基丁氧基、1,2-二甲基丁氧基、1,3-二甲基丁氧基、2,3-二甲基丁氧基、2-乙基丁氧基、庚氧基、1-甲基己氧基、2-甲基己氧基、3-甲基己氧基、4-甲基己氧基、5-甲基己氧基、1-丙基丁氧基、4,4-二甲基戊氧基、辛氧基、1-甲基庚氧基、2-甲基庚氧基、3-甲基庚氧基、4-甲基庚氧基、5-甲基庚氧基、6-甲基庚氧基、1-丙基戊氧基、2-乙基己氧基、5,5-二甲基己氧基、壬氧基、3-甲基辛氧基、4-甲基辛氧基、5-甲基辛氧基、6-甲基辛氧基、1-丙基己氧基、2-乙基庚氧基、6,6-二甲基庚氧基、癸氧基、1-甲基壬氧基、3-甲基壬氧基、8-甲基壬氧基、3-乙基辛氧基、3,7-二甲基辛氧基、7,7-二甲基辛氧基、十一烷氧基、4,8-二甲基壬氧基、十二烷氧基、十三烷氧基、十四烷氧基、十五烷氧基、3,7,11-三甲基十二烷氧基,十六烷氧基,4,8,12-三甲基十三烷氧基、1-甲基十五烷氧基、14-甲基十五烷氧基、13,13-二甲基十四烷氧基、15-甲基十六烷氧基等直链或支链烷氧基;三氟甲氧基、2-氟乙氧基、2,2,2-三氟乙氧基、五氟乙氧基、1,1,2,2-四氟乙氧基、七氟丙氧基、九氟丁氧基、十一氟戊氧基、十三氟己氧基、3-氟丙氧基、4-氟丁氧基、5-氟戊氧基、6-氟己氧基、五氟乙基甲氧基、七氟丙基甲氧基、2-(九氟丁基)乙氧基、2-(十三氟己基)乙氧基、2-(十七氟辛基)乙氧基、氯甲氧基、二氯甲氧基、2-氯乙氧基、3-氯丙氧基、溴甲氧基、2-溴乙氧基等卤原子取代的直链或支链烷氧基,优选碳原子数1~16的烷氧基(该烷氧基可被氟原子或氯原子取代),更优选碳原子数1~16的烷氧基(该烷氧基可被氟原子取代)。
作为取代基组A、B和C中的“碳原子数1~16的烷硫基(该烷硫基可被卤原子取代)”,可列举例如,甲硫基、乙硫基、丙硫基、异丙硫基、丁硫基、异丁硫基、仲丁硫基、叔丁硫基、戊硫基、异戊硫基、2-甲基丁硫基、新戊硫基、1-乙基丙硫基、己硫基、异己硫基、4-甲基戊硫基、3-甲基戊硫基、2-甲基戊硫基、1-甲基戊硫基、3,3-二甲基丁硫基、2,2-二甲基丁硫基、1,1-二甲基丁硫基、1,2-二甲基丁硫基、1,3-二甲基丁硫基、2,3-二甲基丁硫基、2-乙基丁硫基、庚硫基、1-甲基己硫基、2-甲基己硫基、3-甲基己硫基、4-甲基己硫基、5-甲基己硫基、1-丙基丁硫基、4,4-二甲基戊硫基、辛硫基、1-甲基庚硫基、2-甲基庚硫基、3-甲基庚硫基、4-甲基庚硫基、5-甲基庚硫基、6-甲基庚硫基、1-丙基戊硫基、2-乙基己硫基、5,5-二甲基己硫基、壬硫基、3-甲基辛硫基、4-甲基辛硫基、5-甲基辛硫基、6-甲基辛硫基、1-丙基己硫基、2-乙基庚硫基、6,6-二甲基庚硫基、癸硫基、1-甲基壬硫基、3-甲基壬硫基、8-甲基壬硫基、3-乙基辛硫基、3,7-二甲基辛硫基、7,7-二甲基辛硫基、十一烷硫基、4,8-二甲基壬硫基、十二烷硫基、十三烷硫基、十四烷硫基、十五烷硫基、3,7,11-三甲基十二烷硫基,十六烷硫基,4,8,12-三甲基十三烷硫基、1-甲基十五烷硫基、14-甲基十五烷硫基、13,13-二甲基十四烷硫基、15-甲基十六烷硫基等直链或支链烷硫基;三氟甲硫基、2-氟乙硫基、2,2,2-三氟乙硫基、五氟乙硫基、1,1,2,2-四氟乙硫基、七氟丙硫基、九氟丁硫基、十一氟戊硫基、十三氟己硫基、3-氟丙硫基、4-氟丁硫基、5-氟戊硫基、6-氟己硫基、五氟乙基甲硫基、七氟丙基甲硫基、2-(九氟丁基)乙硫基、2-(十三氟己基)乙硫基、2-(十七氟辛基)乙硫基、氯甲硫基、二氯甲硫基、2-氯乙硫基、3-氯丙硫基、溴甲硫基、2-溴乙硫基等卤原子取代的直链或支链烷硫基,优选碳原子数1~16的烷硫基(该烷硫基可被氟原子或氯原子取代),更优选碳原子数1~16的烷硫基(该烷硫基可被氟原子取代)。
作为取代基组A中的“碳原子数6~10的芳基偶氮基”,可列举例如,苯基偶氮基、1-萘基偶氮基、2-萘基偶氮基等,优选苯基偶氮基。
取代基组A中的“含有1~4个氮原子、硫原子或氧原子的杂环基”与前述定义相同,优选含有1~3个氮原子、硫原子或氧原子的5或6元杂环基。
取代基组A,优选由卤原子,羟基,氨基(该氨基可被碳原子数1~6的烷基取代),硝基,氰基,羧基,碳原子1~4的烷氧羰基,氨基甲酰基,碳原子数1~4的亚烷基二氧基,苄氧基,碳原子数1~16的烷基(该烷基可被氟原子或氯原子取代),碳原子数2~16的链烯基,碳原子数1~16的烷氧基(该烷氧基可被氟原子或氯原子取代),碳原子数1~16的烷硫基(该烷硫基可被氟原子或氯原子取代),苯基偶氮基,和含有1~3个氮原子、硫原子或氧原子的5或6元杂环基组成的取代基组A1;
更优选由氟原子或氯原子,羟基,氨基(该氨基可被碳原子数1~3的烷基取代),硝基,氰基,羧基,碳原子数1~4的烷氧羰基,氨基甲酰基,碳原子数1~4的亚烷基二氧基,苄氧基,碳原子数1~16的烷基(该烷基可被氟原子取代),碳原子数2~16的链烯基,碳原子数1~16的烷氧基(该烷氧基可被氟原子取代),碳原子数1~16的烷硫基(该烷硫基可被氟原子取代),苯基偶氮基,和含有1~3个氮原子、硫原子或氧原子的5或6元杂环基组成的取代基组A2。
取代基组B,优选由氧代基,硫代氧代基,亚氨基,卤原子,羟基,氨基(该氨基可被碳原子数1~6的烷基取代),硝基,氰基,羧基,碳原子1~4的烷氧羰基,氨基甲酰基,苄氧基,碳原子数1~16的烷基(该烷基可被氟原子或氯原子取代),碳原子数2~16的链烯基,碳原子数1~16的烷氧基(该烷氧基可被氟原子或氯原子取代),和碳原子数1~16的烷硫基(该烷硫基可被氟原子或氯原子取代)组成的取代基组B1;
更优选由氧代基,硫氧代基,亚氨基,卤原子,羟基,氨基(该氨基可被碳原子数1~3的烷基取代),硝基,氰基,羧基,碳原子1~4的烷氧羰基,氨基甲酰基,苄氧基,碳原子数1~16的烷基(该烷基可被氟原子取代),碳原子数2~16的链烯基,碳原子数1~16的烷氧基(该烷氧基可被氟原子取代),和碳原子数1~16的烷硫基(该烷硫基可被氟原子取代)组成的取代基组B2。
取代基组C,优选由氟原子或氯原子,羟基,氨基,硝基,氰基,羧基,碳原子1~4的烷氧羰基,氨基甲酰基,碳原子数1~16的烷氧基(该烷氧基可被氟原子或氯原子取代),和碳原子数1~16的烷硫基(该烷硫基可被氟原子或氯原子取代)组成的取代基组C1;
更优选,由氟原子,羟基,氨基,硝基,氰基,羧基,碳原子1~4的烷氧羰基,氨基甲酰基,碳原子数1~16的烷氧基(该烷氧基可被氟原子取代),和碳原子数1~16的烷硫基(该烷硫基可被氟原子取代)组成的取代基组C2。
式(a)所示基团中,m优选是0,n优选是1~12的整数,更优选是4~8的整数。
作为R1的“(2)可具有取代基的碳原子数6~10的芳基(该取代基表示选自取代基组A的基团)”,可列举例如,苯基、4-甲基苯基、4-乙基苯基、4-丙基苯基、4-异丙基苯基、4-丁基苯基、4-仲丁基苯基、4-戊基苯基、4-己基苯基、4-庚基苯基、4-辛基苯基、4-癸基苯基、3-甲基苯基、3-乙基苯基、3-异丙基苯基、2-乙基苯基、2-丙基苯基、2-异丙基苯基、2-丁基苯基、4-乙烯基苯基、4-三氟甲基苯基、2,4-二甲基苯基、3,4-二甲基苯基、3,5-二甲基苯基、2,4,6-三甲基苯基、2-甲氧基苯基、2-乙氧苯基、3-乙氧苯基、4-甲氧苯基、4-乙氧苯基、3-异丙氧苯基、4-异丙氧苯基、4-丁氧苯基、4-戊氧苯基、4-己氧苯基、3-苄氧苯基、2-甲基-4-甲氧苯基、3-苯氧苯基、3,4-亚甲基二氧苯基、3,5-二甲氧苯基、3,4,5-三甲氧苯基、2-氟苯基、3-氟苯基、4-氟苯基、4-氯苯基、4-溴苯基、4-碘苯基、3-氯苯基、3-碘苯基、2,3-二氟苯基、2,4-二氟苯基、2,5-二氟苯基、2,6-二氟苯基、3,4-二氟苯基、3,5-二氟苯基、2,3,4-三氟苯基、2,3,6-三氟苯基、2,4,6-三氟苯基、2,4,5-三氟苯基、3-氯-4-氟苯基、3-三氟甲基-4-氟苯基、3-三氟甲氧苯基、4-三氟甲氧苯基、4-甲硫基苯基、4-三氟甲硫基苯基、3-甲硫基苯基、3-氟-4-甲基苯基、3-氯-4-甲基苯基、3-甲基-4-溴苯基、3-硝基-4-氟苯基、3-硝基-4-氯苯基、4-(五氟乙基甲氧)苯基、4-(七氟丙基甲氧)苯基、4-{2-(九氟丁基)乙氧}苯基、4-{2-(十三氟己基)乙氧}苯基、4-{2-(十七氟辛基)乙氧}苯基、4-(2-氟乙基)苯基、4-(3-氟丙基)苯基、4-(4-氟丁基)苯基、4-(5-氟戊基)苯基、2-硝基苯基、3-硝基苯基、4-硝基苯基、2-羟基苯基、3-羟基苯基、4-羟基苯基、3-氰基苯基、4-吗啉代苯基、4-苯基偶氮基苯基、萘-1-基、萘-2-基、3-氨基苯基、4-二甲基氨基等;
优选苯基、4-甲基苯基、4-乙基苯基、4-丙基苯基、4-异丙基苯基、4-丁基苯基、4-仲丁基苯基、4-戊基苯基、4-己基苯基、4-庚基苯基、4-辛基苯基、4-癸基苯基、3-甲基苯基、3-乙基苯基、3-异丙基苯基、4-乙烯基苯基、4-三氟甲基苯基、3,4-二甲基苯基、3,5-二甲基苯基、3-乙氧苯基、4-甲氧苯基、4-乙氧苯基、3-异丙氧苯基、4-异丙氧苯基、4-丁氧苯基、4-戊氧苯基、4-己氧苯基、3-苄氧苯基、3-苯氧苯基、3,4-亚甲基二氧苯基、3,5-二甲氧苯基、3,4,5-三甲氧苯基、3-氟苯基、4-氟苯基、4-氯苯基、4-溴苯基、4-碘苯基、3-氯苯基、3-碘苯基、3,4-二氟苯基、3,5-二氟苯基、3-氯-4-氟苯基、3-三氟甲基-4-氟苯基、3-三氟甲氧苯基、4-三氟甲氧苯基、4-甲硫基苯基、4-三氟甲硫基苯基、3-甲硫基苯基、3-氟-4-甲基苯基、3-氯-4-甲基苯基、3-甲基-4-溴苯基、3-硝基-4-氟苯基、3-硝基-4-氯苯基、4-(五氟乙基甲氧)苯基、4-(七氟丙基甲氧)苯基、4-{2-(九氟丁基)乙氧}苯基、4-{2-(十三氟己基)乙氧}苯基、4-{2-(十七氟辛基)乙氧}苯基、4-(2-氟乙基)苯基、4-(3-氟丙基)苯基、4-(4-氟丁基)苯基、4-(5-氟戊基)苯基、3-硝基苯基、4-硝基苯基、2-羟基苯基、3-羟基苯基、4-羟基苯基、3-氰基苯基、4-吗啉代苯基或4-苯基偶氮基苯基;
更优选苯基、4-乙基苯基、4-丙基苯基、4-丁基苯基、4-戊基苯基、4-己基苯基、3-甲基苯基、3-乙基苯基、3-异丙基苯基、4-三氟甲基苯基、4-丁氧苯基、4-戊氧苯基、4-己氧苯基、3,5-二甲氧苯基、3,4,5-三甲氧苯基、3-氟苯基、4-氟苯基、4-氯苯基、3-氯苯基、3-碘苯基、3,4-二氟苯基、3,5-二氟苯基、3-氯-4-氟苯基、3-三氟甲基-4-氟苯基、3-三氟甲氧苯基、4-三氟甲氧苯基、4-甲硫基苯基、4-三氟甲硫基苯基、3-甲硫基苯基、3-氟-4-甲基苯基、3-氯-4-甲基苯基、4-(五氟乙基甲氧)苯基、4-(七氟丙基甲氧)苯基、4-{2-(九氟丁基)乙氧}苯基、4-(2-氟乙基)苯基、4-(3-氟丙基)苯基、4-(4-氟丁基)苯基、4-(5-氟戊基)苯基、3-甲基-4-溴苯基、3-硝基-4-氟苯基。
作为R1中的“(3)可具有取代基的含有1~4个氮原子、硫原子或氧原子的杂环基(该杂环基可具有选自取代基组B的取代基”,可列举例如,2-吡啶基、3,5-二氯-2-吡啶基、3-苄氧-2-吡啶基、3-甲基-2-吡啶基、4-甲基-2-吡啶基、5-氯-2-吡啶基、3-吡啶基、2-氯-3-吡啶基、6-甲氧-3-吡啶基、4-吡啶基、2,3,5,6-四氟-4-吡啶基、3-喹啉基、2-噻吩基、3-甲氧羰基-5-乙酰基-2-噻吩基、3-噻吩基、2-甲氧羰基-3-噻吩基、2-乙酰基-3-噻吩基、2-氨基甲酰基-3-噻吩基、2-呋喃基、5-甲氧羰基-2-呋喃基、2-噻唑基、5-硝基-2-噻唑基、4-甲基-2-噻唑基等;
优选2-吡啶基、3-苄氧-2-吡啶基、4-甲基-2-吡啶基、5-氯-2-吡啶基、3-吡啶基、6-甲氧-3-吡啶基、4-吡啶基、2,3,5,6-四氟-4-吡啶基、2-噻吩基、3-噻吩基、2-呋喃基、5-甲氧羰基-2-呋喃基、2-噻唑基、5-硝基-2-噻唑基或4-甲基-2-噻唑基。
作为R1中的“(4)具有1~3个相同或不同的可具有取代基的碳原子数6~10的芳基的碳原子数1~14的烷基(该芳基部分的取代基为选自取代基组A的基团)”,可列举例如,苄基、2-甲基苄基、4-甲基苄基、4-氟苄基、2-甲氧苄基、4-甲氧苄基、3,4,5-三甲氧苄基、3,4-亚甲基二氧苄基、1-苯乙基、2-萘基、2-苯基乙基、2-(4-甲基苯基)乙基、2-(2-甲氧苯基)乙基、2-(3-甲氧苯基)乙基、2-(4-甲氧苯基)乙基、2-(3,4-二甲氧苯基)乙基、2-(4-氟苯基)乙基、2-(2-氯苯基)乙基、2-(3-氯苯基)乙基、2-(4-氯苯基)乙基、2-(2,4-二氯苯基)乙基、2-(4-羟基苯基)乙基、2,2-二苯基乙基、3-苯基丙基、6-苯基己基、10-苯基癸基、3-(4-己氧苯基)丙基等;
优选苄基、2-甲基苄基、4-甲基苄基、4-氟苄基、2-甲氧苄基、2-萘基、2-苯乙基、2-(4-甲基苯基)乙基、2-(4-甲氧苯基)乙基、2-(3,4-二甲氧苯基)乙基、2-(4-氟苯基)乙基、2-(2-氯苯基)乙基、2-(3-氯苯基)乙基、2-(4-氯苯基)乙基、2-(2,4-二氯苯基)乙基、3-苯基丙基或6-苯基己基。
作为R1中的“(5)具有1~3个相同或不同的可具有取代基的含有1~4个氮原子、硫原子或氧原子的杂环基的碳原子数1~14的烷基(该杂环基部分的取代基为选自取代基组B的基团)”,可列举例如,2-呋喃基甲基、(3-甲基-2-呋喃基)甲基、3-呋喃基甲基、2-噻吩基甲基、2-吡啶基甲基、4-氟-2-吡啶基甲基、2-(2-呋喃基)乙基、2-(3-甲基-2-呋喃基)乙基、2-吗啉代乙基、3-(1-咪唑基)丙基、2-喹啉基甲基、3,3-(3-吡啶基)丙基等;
优选2-呋喃基甲基、3-呋喃基甲基、2-噻吩基甲基、2-吡啶基甲基、4-氟-2-吡啶基甲基、3-(1-咪唑基)丙基或2-喹啉基甲基。
作为R1中的“(6)可具有取代基的碳原子数1~22的烷基(该取代基表示选自取代基组C的基团)”,可列举,甲基、乙基、丙基、异丙基、丁基、仲丁基、叔丁基、戊基、己基、庚基、辛基、壬基、癸基、十一烷基、十二烷基、十三烷基、十四烷基、十五烷基、十六烷基、十八烷基、二十烷基、二十二烷基、1-甲基庚基、2-乙基己基、环己基、4-甲基环己基、4-叔丁基环己基、环庚基、环辛基、环十二烷基、环己基甲基、3-乙氧丙基、3-甲硫丙基、2,2-二甲氧乙基、2,2-二乙氧乙基、2-羟基乙基、2-氨基乙基、4-羟基丁基、5-羟基戊基、5-氟戊基、3-硝基丙基、2-氰基乙基等;
优选丙基、异丙基、丁基、仲丁基、叔丁基、戊基、己基、庚基、辛基、壬基、癸基、十一烷基、十二烷基、十三烷基、环己基、4-甲基环己基、环庚基、环辛基、环十二烷基、3-乙氧丙基或3-甲硫丙基。
作为R1中的“(7)可具有取代基的碳原子数2~22的链烯基(该取代基表示为上述(2)或(3)的基团或选自取代基组C的基团)”,可列举例如,乙烯基、烯丙基、反-2-己烯-1-基、顺-2-己烯-1-基、反-2-戊烯-1-基、反-2,4-己二烯-1-基、2-(1-环己烯)乙基、4-甲基-反-2-己烯-1-基、6-氯-反-3-己烯-1-基、6-硝基-反-3-己烯-1-基、6-氰基-反-3-己烯-1-基等;
优选反-2-己烯-1-基、顺-2-己烯-1-基、反-2-戊烯-1-基、反-2,4-己二烯-1-基、4-甲基-反-2-己烯-1-基、6-氯-反-3-己烯-1-基。
作为R1中的“(8)式(a)所示基团[式中,n表示1~20的整数,m表示0或2。],优选m是0或2,n是1~12的整数的基团;更优选m是0或2,n是4~8的整数的基团;最优选m是0,n是4~8的整数的基团。
R1优选上述的“(2)可具有取代基的碳原子数6~10的芳基”、“(4)具有1~3个相同或不同的可具有取代基的碳原子数6~10的芳基的碳原子数1~14的烷基”、“(5)具有1~3个相同或不同的可具有取代基的含有1~4个氮原子、硫原子或氧原子的杂环基的碳原子数1~14的烷基”、“(6)可具有取代基的碳原子数1~22的烷基”、“(7)可具有取代基的碳原子数2~22的链烯基”、“(8)式(a)所示基团”;
更优选“(2)可具有取代基的碳原子数6~10的芳基”、“(6)可具有取代基的碳原子数1~22的烷基”或“(7)可具有取代基的碳原子数2~22的链烯基”、或“(8)式(a)所示基团”;
更优选“(2)可具有取代基的碳原子数6~10的芳基”、“(6)可具有取代基的碳原子数1~22的烷基”或“(7)可具有取代基的碳原子数2~22的链烯基(该取代基是选自取代基组C的基团)”;
特别优选“(2)可具有取代基的碳原子数6~10的芳基”或“(6)可具有取代基的碳原子数1~22的烷基”;
最优选“(2)可具有取代基的碳原子数6~10的芳基”。
R2优选“(1)氢原子”“(6)可具有取代基的碳原子数1~22的烷基”或“(7)可具有取代基的碳原子数2~22的链烯基”,更优选氢原子、未取代的碳原子数1~22的烷基或未取代的碳原子数2~22的链烯基;更优选氢原子、未取代的碳原子数6~20的烷基或未取代的碳原子数10~20的链烯基;特别优选氢原子或未取代的碳原子数6~20的烷基;最优选氢原子。
R3优选是羟基。
作为通式(I)所示化合物,优选下面的化合物。
1.关于X1
(1-1)X1是式-N(R4)-所示基团的化合物。
(1-2)X1是式-N(R4)-所示基团(式中,R4表示氢原子或碳原子数1~3的烷基)的化合物。
(1-3)X1是式-NH-所示基团的化合物。
2.关于X2
(2-1)X2是式-N(R5)-所示基团的化合物。
(2-2)X2是式-N(R5)-所示基团(式中,R5表示氢原子或碳原子数1~3的烷基)的化合物。
(2-3)X2是式-NH-所示基团的化合物。
3.关于R1
(3-1)R1是氢原子的化合物。
(3-2)R1是可具有取代基的碳原子数6~10的芳基(该取代基表示选自取代基组A的基团)的化合物。
(3-2-1)(3-2)中的取代基是选自取代基组A1的基团的化合物。
(3-2-2)(3-2)中的取代基是选自取代基组A2的基团的化合物。
(3-2-3)(3-2)中的芳基部分是可具有取代基的苯基、1-萘基或2-萘基(该取代基表示选自取代基组A的基团)的化合物。
(3-2-4)(3-2)中的芳基部分是可具有取代基的苯基(该取代基表示选自取代基组A的基团)的化合物。
(3-3)R1是可具有取代基的、含有1~4个氮原子、硫原子或氧原子的杂环基(该取代基表示选自取代基组B的基团)的化合物。
(3-3-1)(3-3)中的取代基是选自取代基组B1的基团的化合物。
(3-3-2)(3-3)中的取代基是选自取代基组B2的基团的化合物。
(3-3-3)(3-3)中的杂环部分是可具有取代基的5或6元芳族杂环基或与苯环稠合的5或6元芳族杂环基(该取代基表示选自取代基组B的基团)的化合物。
(3-4)R1是具有1~3个相同或不同的可具有取代基的碳原子数6~10的芳基的碳原子数1~14的烷基(该取代基表示选自取代基组A的基团)的化合物。
(3-4-1)(3-4)中的取代基是选自取代基组A1的基团的化合物。
(3-4-2)(3-4)中的取代基是选自取代基组A2的基团的化合物。
(3-4-3)(3-4)中的芳基部分是可具有取代基的苯基、1-萘基或2-萘基(该取代基表示选自取代基组A的基团)的化合物。
(3-4-4)(3-4)中的芳基部分是可具有取代基的苯基的化合物。
(3-4-5)(3-4)中的烷基部分是碳原子数1~8的烷基的化合物。
(3-4-6)(3-4)中的烷基部分是碳原子数1~4的烷基的化合物。
(3-4-7)(3-4)中的烷基部分是碳原子数1~2的烷基的化合物。
(3-4-8)(3-4)中的烷基部分是碳原子数为2的烷基的化合物。
(3-5)R1是具有1~3个相同或不同的可具有取代基的含有1~4个氮原子、硫原子或氧原子的杂环基的碳原子数1~14的烷基(该取代基表示选自取代基组B的基团)的化合物。
(3-5-1)(3-5)中的取代基是选自取代基组B1的基团的化合物。
(3-5-2)(3-5)中的取代基是选自取代基组B2的基团的化合物。
(3-5-3)(3-5)中的杂环部分是可具有取代基的5或6元芳族杂环基或与苯环稠合的5或6元芳族杂环基(该取代基表示选自取代基组B的基团)的化合物。
(3-5-4)(3-5)中的烷基部分是碳原子数1~8的烷基的化合物。
(3-5-5)(3-5)中的烷基部分是碳原子数1~4的烷基的化合物。
(3-5-6)(3-5)中的烷基部分是碳原子数1或2的烷基的化合物。
(3-5-7)(3-5)中的烷基部分是碳原子数为2的烷基的化合物。
(3-6)R1是可具有取代基的碳原子数1~22的烷基(该取代基表示选自取代基组C的基团)的化合物。
(3-6-1)(3-6)中的取代基是选自取代基组C1的基团的化合物。
(3-6-2)(3-6)中的取代基是选自取代基组C2的基团的化合物。
(3-6-3)(3-6)中的R1是可具有取代基的碳原子数1~18的烷基(该取代基表示选自取代基组C的基团)的化合物。
(3-7)R1是可具有取代基的碳原子数2~22的链烯基(该取代基表示选自上述(2)或(3)的基团或选自取代基组C的基团)的化合物。
(3-7-1)(3-7)中的R1是可具有取代基的碳原子数2~22的链烯基(该取代基表示选自取代基组C的基团)的化合物。
(3-7-2)(3-7)中的R1是未取代的碳原子数2~22的链烯基的化合物。
(3-7-3)(3-7)中的R1是未取代的碳原子数2~18的链烯基的化合物。
(3-8)R1是式(a)所示基团的化合物。
(3-8-1)(3-8)中m是0的化合物。
(3-8-2)(3-8)中n是1~12的整数的化合物。
(3-8-3)(3-8)中n是4~8的整数的化合物。
(3-8-4)(3-8)中m是0或2,n是4~8的整数的化合物。
(3-8-5)(3-8)中m是0,n是4~8的整数的化合物。
4.关于R2
(4-1)R2是氢原子、可具有取代基的碳原子数1~22的烷基(该取代基表示选自取代基组C的基团)或可具有取代基的碳原子数2~22的链烯基(该取代基是选自取代基组C的基团)的化合物。
(4-2)R2是氢原子、未取代的碳原子数1~22的烷基或未取代的碳原子数2~22的链烯基的化合物。
(4-3)R2是氢原子、未取代的碳原子数6~20的烷基或未取代的碳原子数10~20的链烯基的化合物。
(4-4)R2是氢原子或未取代的碳原子数6~20的烷基的化合物。
(4-5)R2是未取代的碳原子数6~20的烷基的化合物。
(4-6)R2是氢原子的化合物。
5.关于R3
(5-1)R3是氢原子的化合物。
(5-2)R3是羟基的化合物。
6.更优选关于X1、X2、R1、R2和R3将上述优选的取代基适当组合得到的化合物,可列举例如如下的组合。另外,可采取的组合并不限于下列例子。
(6-1)X1是式-N(R4)-所示基团,X2是式-N(R5)-所示基团,R1是(2)可具有取代基的碳原子数6~10的芳基(该取代基表示选自取代基组A的基团)、(4)具有1~3个相同或不同的可具有取代基的碳原子数6~10的芳基的碳原子数1~14的烷基(该取代基表示选自取代基组A的基团)、(5)具有1~3个相同或不同的可具有取代基的含有1~4个氮原子、硫原子或氧原子的杂环基的碳原子数1~14的烷基(该取代基表示选自取代基组B的基团)、(6)可具有取代基的碳原子数1~22的烷基(该取代基表示选自取代基组C的基团)、(7)可具有取代基的碳原子数2~22的链烯基(该取代基表示选自权利要求1的R1定义中的(2)或(3)的基团或选自取代基组C的基团)、或(8)式(a)所示基团,R2是氢原子或未取代的碳原子数6~20的烷基,R3是氢原子或羟基的化合物。
(6-2)X1和X2是式-NH-所示基团,R1是(2)可具有取代基的碳原子数6~10的芳基(该取代基表示选自取代基组A的基团)、(4)具有1~3个相同或不同的可具有取代基的碳原子数6~10的芳基的碳原子数1~14的烷基(该取代基表示选自取代基组A的基团)、(5)具有1~3个相同或不同的可具有取代基的含有1~4个氮原子、硫原子或氧原子的杂环基的碳原子数1~14的烷基(该取代基表示选自取代基组B的基团)、(6)可具有取代基的碳原子数1~22的烷基(该取代基表示选自取代基组C的基团)、(7)可具有取代基的碳原子数2~22的链烯基(该取代基表示选自权利要求1的R1定义中的(2)或(3)的基团或选自取代基组C的基团)、或(8)式(a)所示基团,R2是氢原子或未取代的碳原子数6~20的烷基,R3是氢原子或羟基的化合物。
(6-3)X1和X2是式-NH-所示基团,R1是(2)可具有取代基的碳原子数6~10的芳基(该取代基表示选自取代基组A的基团)、(6)可具有取代基的碳原子数1~22的烷基(该取代基表示选自取代基组C的基团)、(7)可具有取代基的碳原子数2~22的链烯基(该取代基表示选自权利要求1的R1定义中的(2)或(3)的基团或选自取代基组C的基团)、或(8)式(a)所示基团,R2是氢原子或未取代的碳原子数6~20的烷基,R3是氢原子或羟基的化合物。
(6-4)X1和X2是式-NH-所示基团,R1是(2)可具有取代基的碳原子数6~10的芳基(该取代基表示选自取代基组A的基团)或(6)可具有取代基的碳原子数1~22的烷基(该取代基表示选自取代基组C的基团),R2是氢原子或未取代的碳原子数6~20的烷基,R3是氢原子或羟基的化合物。
(6-5)X1和X2是式-NH-所示基团,R1是(2)可具有取代基的碳原子数6~10的芳基(该取代基表示选自取代基组A的基团),R2是氢原子或未取代的碳原子数6~20的烷基,R3是氢原子或羟基的化合物。
(6-6)X1和X2是式-NH-所示基团,R1是可具有取代基的苯基(该取代基表示选自取代基组A的基团),R2是氢原子,R3是羟基的化合物。
(6-7)X1和X2是式-NH-所示基团,R1是可具有取代基的苯基(该取代基表示选自取代基组A的基团),R2是未取代的碳原子数6~20的烷基,R3是羟基的化合物。
(6-8)X1和X2是式-NH-所示基团,R1是可具有取代基的苯基(该取代基表示选自取代基组A的基团),R2是氢原子,R3是氢原子的化合物。
通式(I)所示化合物的“药理上可接受的酯、醚或N-烷基衍生物”是指没有显著的毒性,可作为药物使用的酯、醚或N-烷基衍生物。
由于通式(I)所示化合物中分子内有多个羟基,因此可将任意的羟基可通过化学改性为药物允许的、不显示显著毒性的基团,转化为药理上允许的酯或醚衍生物。另外,由于通式(I)所示化合物中分子内有多个尿嘧啶残基,因此其3位氮原子可通过化学改性为药物是允许的、不显示显著毒性的基团,转化为药理上允许的N-烷基衍生物。
这些衍生物中优选的物质是药理上可接受的酯或醚衍生物,更优选药理上可接受的酯衍生物。
作为药理上可接受的酯衍生物的酯残基,可列举,与甲基、乙基、丙基、异丙基、丁基、异丁基、仲丁基、叔丁基、戊基、异戊基、2-甲基丁基、新戊基、1-乙基丙基、己基、异己基、4-甲基戊基、3-甲基戊基、2-甲基戊基、1-甲基戊基、3,3-二甲基丁基、2,2-二甲基丁基、1,1-二甲基丁基、1,2-二甲基丁基、1,3-二甲基丁基、2,3-二甲基丁基、2-乙基丁基、庚基、1-甲基己基、2-甲基己基、3-甲基己基、4-甲基己基、5-甲基己基、1-丙基丁基、4,4-二甲基戊基、辛基、1-甲基庚基、2-甲基庚基、3-甲基庚基、4-甲基庚基、5-甲基庚基、6-甲基庚基、1-丙基戊基、2-乙基己基、5,5-二甲基己基、壬基、3-甲基辛基、4-甲基辛基、5-甲基辛基、6-甲基辛基、1-丙基己基、2-乙基庚基、6,6-二甲基庚基、癸基、1-甲基壬基、3-甲基壬基、8-甲基壬基、3-乙基辛基、3,7-二甲基辛基、7,7-二甲基辛基、十一烷基、4,8-二甲基壬基、十二烷基、十三烷基、十四烷基、十五烷基、3,7,11-三甲基十二烷基、十六烷基、4,8,12-三甲基十三烷基、1-甲基十五烷基、14-甲基十五烷基、13,13-二甲基十四烷基、十七烷基、15-甲基十六烷基、十八烷基、1-甲基十七烷基、十九烷基、二十烷基、3,7,11,15-四甲基十六烷基、二十一烷基等碳原子数1~21的直链或支链烷基结合了的羰基或氧基羰基;
与乙烯基、1-丙烯基、2-丙烯基、1-甲基-2-丙烯基、1-甲基-1-丙烯基、2-甲基-1-丙烯基、2-甲基-2-丙烯基、2-乙基-2-丙烯基、1-丁烯基、2-丁烯基、1-甲基-2-丁烯基、1-甲基-1-丁烯基、3-甲基-2-丁烯基、1-乙基-2-丁烯基、3-丁烯基、1-甲基-3-丁烯基、2-甲基-3-丁烯基、1-乙基-3-丁烯基、1-戊烯基、2-戊烯基、1-甲基-2-戊烯基、2-甲基-2-戊烯基、3-戊烯基、1-甲基-3-戊烯基、2-甲基-3-戊烯基、4-戊烯基、1-甲基-4-戊烯基、2-甲基-4-戊烯基、1-己烯基、2-己烯基、3-己烯、4-己烯基、5-己烯基、顺-8-十七碳烯基、顺、顺-8、11-十七碳二烯基、顺、顺、顺-8、11、14-十七碳三烯基、顺-10-十九碳烯基、顺-12-二十碳烯基、乙炔基、2-丙炔基、1-甲基-2-丙炔基、2-甲基-2-丙炔基、2-乙基-2-丙炔基、2-丁炔基、1-甲基-2-丁炔基、2-甲基-2-丁炔基、1-乙基-2-丁炔基、3-丁炔基、1-甲基-3-丁炔基、2-甲基-3-丁炔基、1-乙基-3-丁炔基、2-戊炔基、1-甲基-2-戊炔基、2-甲基-2-戊炔基、3-戊炔基、1-甲基-3-戊炔基、2-甲基-3-戊炔基、4-戊炔基、1-甲基-4-戊炔基、2-甲基-4-戊炔基、2-己炔基、3-己炔基、4-己炔基、5-己炔基等的碳原子数2~21的直链或支链不饱和烷基结合了的羰基或氧基羰基;
与甲氧基甲基、乙氧基甲基、甲氧基乙基、乙氧基乙基、三氟甲基、三氯甲基、二氟甲基、二氯甲基、二溴甲基、氟甲基、2,2,2-三氟乙基、2,2,2-三氯乙基、2-溴乙基、2-氯乙基、2-氟乙基、2-碘乙基、3-氯丙基、4-氟丁基、6-碘己基、2,2-二溴乙基、硝基甲基、二硝基甲基、1-硝基乙基、2-硝基乙基、1,2-二硝基乙基等用从碳原子数1~4的烷氧基、卤素(例如,氟、氯、溴、碘,优选氟或氯。以下相同。)和硝基组成的组选出的取代基取代的碳原子数1~21的直链或支链烷基结合的羰基或氧基羰基;
与苄基、α-萘基甲基、β-萘基甲基、茚基甲基、菲基甲基、蒽基甲基、二苯基甲基、三苯基甲基、1-苯乙基、2-苯乙基、1-萘基乙基、2-萘基乙基、1-苯基丙基、2-苯基丙基、3-苯基丙基、1-萘基丙基、2-萘基丙基、3-萘基丙基、1-苯基丁基、2-苯基丁基、3-苯基丁基、4-苯基丁基、1-萘基丁基、2-萘基丁基、3-萘基丁基、4-萘基丁基、1-苯基戊基、2-苯基戊基、3-苯基戊基、4-苯基戊基、5-苯基戊基、1-萘基戊基、2-萘基戊基、3-萘基戊基、4-萘基戊基、5-萘基戊基、1-苯基己基、2-苯基己基、3-苯基己基、4-苯基己基、5-苯基己基、6-苯基己基、1-萘基己基、2-萘基己基、3-萘基己基、4-萘基己基、5-萘基己基、6-萘基己基等可被由碳原子数1~4的烷基、碳原子数1~4的烷氧基、卤素和硝基组成的组选出的取代基取代的(碳原子数6~10的芳基)-(碳原子数1~21的烷基)结合的羰基或氧基羰基;
与苯基、萘基、2-氟苯基、3-氟苯基、4-氟苯基、2-氯苯基、3-氯苯基、4-氯苯基、2-溴苯基、3-溴苯基、4-溴苯基、3,5-二氟苯基、2,5-二氟苯基、2,6-二氟苯基、2,4-二氟苯基、3,5-二溴苯基、2,5-二溴苯基、2,6-二氯苯基、2,4-二氯苯基、2,3,6-三氟苯基、2,3,4-三氟苯基、3,4,5-三氟苯基、2,5,6-三氟苯基、2,4,6-三氟苯基、2,3,6-三溴苯基、2,3,4-三溴苯基、3,4,5-三溴苯基、2,5,6-三氯苯基、2,4,6-三氯苯基、1-氟-2-萘基、2-氟-1-萘基、3-氟-1-萘基、1-氯-2-萘基、2-氯-1-萘基、3-溴-1-萘基、3,8-二氟-1-萘基、2,3-二氟-1-萘基、4,8-二氟-1-萘基、5,6-二氟-1-萘基、3,8-二氯-1-萘基、2,3-二氯-1-萘基、4,8-二溴-1-萘基、5,6-二溴-1-萘基、2,3,6-三氟-1-萘基、2,3,4-三氟-1-萘基、3,4,5-三氟-1-萘基、4,5,6-三氟-1-萘基、2,4,8-三氟-1-萘基、2-甲基苯基、3-甲基苯基、4-甲基苯基、2-乙基苯基、3-丙基苯基、4-乙基苯基、2-丁基苯基、3-戊基苯基、4-戊基苯基、3,5-二甲基苯基、2,5-二甲基苯基、2,6-二甲基苯基、2,4-二甲基苯基、3,5-二丁基苯基、2,5-二戊基苯基、2,6-二丙基甲基苯基、2,4-二丙基苯基、2,3,6-三甲基苯基、2,3,4-三甲基苯基、3,4,5-三甲基苯基、2,5,6-三甲基苯基、2,4,6-三甲基苯基、2,3,6-三丁基苯基、2,3,4-三戊基苯基、3,4,5-三丁基苯基、2,5,6-三丙基甲基苯基、2,4,6-三丙基苯基、1-甲基-2-萘基、2-甲基-1-萘基、3-甲基-1-萘基、1-乙基-2-萘基、2-丙基-1-萘基、3-丁基-1-萘基、3,8-二甲基-1-萘基、2,3-二甲基-1-萘基、4,8-二甲基-1-萘基、5,6-二甲基-1-萘基、3,8-二乙基-1-萘基、2,3-二丙基-1-萘基、4,8-二戊基-1-萘基、5,6-二丁基-1-萘基、2,3,6-三甲基-1-萘基、2,3,4-三甲基-1-萘基、3,4,5-三甲基-1-萘基、4,5,6-三甲基-1-萘基、2,4,8-三甲基-1-萘基、2-甲氧基苯基、3-甲氧基苯基、4-甲氧基苯基、2-乙氧基苯基、3-丙氧基苯基、4-乙氧基苯基、2-丁氧基苯基、3-戊氧基苯基、 4-戊氧基苯基、3,5-二甲氧基苯基、2,5-二甲氧基苯基、2,6-二甲氧基苯基、2,4-二甲氧基苯基、3,5-二丁氧基苯基、2,5-二戊氧基苯基、2,6-二丙氧基甲氧基苯基、2,4-二丙氧基苯基、2,3,6-三甲氧基苯基、2,3,4-三甲氧基苯基、3,4,5-三甲氧基苯基、2,5,6-三甲氧基苯基、2,4,6-三甲氧基苯基、2,3,6-三丁氧基苯基、2,3,4-三戊氧基苯基、3,4,5-三丁氧基苯基、2,5,6-三丙氧基苯基、2,4,6-三丙氧基苯基、1-甲氧基-2-萘基、2-甲氧基-1-萘基、3-甲氧基-1-萘基、1-乙氧基-2-萘基、2-丙氧基-1-萘基、3-丁氧基-1-萘基、3,8-二甲氧基-1-萘基、2,3-二甲氧基-1-萘基、4,8-二甲氧基-1-萘基、5,6-二甲氧基-1-萘基、3,8-二乙氧基-1-萘基、2,3-二丙氧基-1-萘基、4,8-二戊氧基-1-萘基、5,6-二丁氧基-1-萘基、2,3,6-三甲氧基-1-萘基、2,3,4-三甲氧基-1-萘基、3,4,5-三甲氧基-1-萘基、4,5,6-三甲氧基-1-萘基、2,4,8-三甲氧基-1-萘基、2-硝基苯基、3-硝基苯基、4-硝基苯基、3,5-二硝基苯基、2,5-二硝基苯基、2,6-二硝基苯基、2,4-二硝基苯基、2,3,6-三硝基苯基、2,3,4-三硝基苯基、3,4,5-三硝基苯基、2,5,6-三硝基苯基、2,4,6-三硝基苯基、1-硝基-2-萘基、2-硝基-1-萘基、3-硝基-1-萘基、3,8-二硝基-1-萘基、2,3-二硝基-1-萘基、4,8-二硝基-1-萘基、5,6-二硝基-1-萘基、2,3,6-三硝基-1-萘基、2,3,4-三硝基-1-萘基、3,4,5-三硝基-1-萘基、4,5,6-三硝基-1-萘基、2,4,8-三硝基-1-萘基等可用由碳原子数1~4的烷基、碳原子数1~4的烷氧基、卤素和硝基组成的组选出的取代基取代的碳原子数6~10个芳基结合的羰基或氧基羰基;
琥珀酰基、戊二酰基、己二酰基等羧基-碳原子数1~10个的烷基-羰基;
具有1个或者具有相同或不同的2个前述碳原子数2~16的烷基的磷酸单烷基酯或二烷基酯残基;或者,
可以用叔丁氧羰基、苄氧羰基或三苯甲基等保护基保护的甘氨酸、丙氨酸、缬氨酸、亮氨酸、异亮氨酸、苯基丙氨酸、脯氨酸、色氨酸、谷氨酰胺、谷氨酸等氨基酸的成酯残基。
其中优选的是,用式RaCO-或RaOCO-表示的碳酰基(カルボアシル)(Ra是氢原子;碳原子数1~21的烷基;具有1~3个的不饱和键的碳原子数2~21的不饱和烷基;具有1~4个的从碳原子数1~4的烷氧基、卤素和硝基组成的组中选出的取代基的碳原子数1~21的烷基;具有1~3个的碳原子数6~10个的芳基作为取代基的碳原子数1~21的烷基,其中芳基可有1~4个从碳原子数1~4的烷基、碳原子数1~4的烷氧基、卤素和硝基组成的组中选出的取代基;或可具有1~4个从碳原子数1~4的烷基、碳原子数1~4的烷氧基、卤素和硝基组成的组中选出的取代基的碳原子数6~10个的芳基。)。
更优选的是,用式RaCO-或RaOCO-表示的碳酰基(カルボアシル)(Ra是碳原子数6~20个的烷基;具有1~3个的双键的碳原子数10~20的链烯基;具有一个三键的碳原子数3~5个的炔基;具有1个碳原子数1~4的烷氧基取代基的碳原子数1~4的烷基;具有1~2个苯基作为取代基的碳原子数1~4的烷基,其中苯基可有1~2个从碳原子数1~2的烷基、碳原子数1~4的烷氧基、氟和氯组成的组中选出的取代基。)。
更优选的是,用式RaCO-或RaOCO-表示的碳酰基(カルボアシル)(Ra是碳原子数6~20的烷基;具有1~3个双键的碳原子数10~20的链烯基)。
作为药理上允许的醚衍生物的醚残基,可列举例如,甲基、乙基、丙基、异丙基、丁基、异丁基、仲丁基、叔丁基、戊基、异戊基、2-甲基丁基、新戊基、1-乙基丙基、己基、异己基、4-甲基戊基、3-甲基戊基、2-甲基戊基、1-甲基戊基、3,3-二甲基丁基、2,2-二甲基丁基、1,1-二甲基丁基、1,2-二甲基丁基、1,3-二甲基丁基、2,3-二甲基丁基、2-乙基丁基、庚基、1-甲基己基、2-甲基己基、3-甲基己基、4-甲基己基、5-甲基己基、1-丙基丁基、4,4-二甲基戊基、辛基、1-甲基庚基、2-甲基庚基、3-甲基庚基、4-甲基庚基、5-甲基庚基、6-甲基庚基、1-丙基戊基、2-乙基己基、5,5-二甲基己基、壬基、3-甲基辛基、4-甲基辛基、5-甲基辛基、6-甲基辛基、1-丙基己基、2-乙基庚基、6,6-二甲基庚基、癸基、1-甲基壬基、3-甲基壬基、8-甲基壬基、3-乙基辛基、3,7-二甲基辛基、7,7-二甲基辛基、十一烷基、4,8-二甲基壬基、十二烷基、十三烷基、十四烷基、十五烷基、3,7,11-三甲基十二烷基、十六烷基、4,8,12-三甲基十三烷基、1-甲基十五烷基、14-甲基十五烷基、13,13-二甲基十四烷基、十七烷基、15-甲基十六烷基、十八烷基、1-甲基十七烷基、十九烷基、二十烷基、3,7,11,15-四甲基十六烷基、二十一烷基等碳原子数1~21的直链或支链烷基;
乙烯基、1-丙烯基、2-丙烯基、1-甲基-2-丙烯基、1-甲基-1-丙烯基、2-甲基-1-丙烯基、2-甲基-2-丙烯基、2-乙基-2-丙烯基、1-丁烯基、2-丁烯基、1-甲基-2-丁烯基、1-甲基-1-丁烯基、3-甲基-2-丁烯基、1-乙基-2-丁烯基、3-丁烯基、1-甲基-3-丁烯基、2-甲基-3-丁烯基、1-乙基-3-丁烯基、1-戊烯基、2-戊烯基、1-甲基-2-戊烯基、2-甲基-2-戊烯基、3-戊烯、1-甲基-3-戊烯基、2-甲基-3-戊烯基、4-戊烯基、1-甲基-4-戊烯基、2-甲基-4-戊烯基、1-己烯基、2-己烯基、3-己烯基、4-己烯基、5-己烯基、顺-8-十七碳烯基、顺、顺-8、11-十七碳二烯基、顺、顺、顺-8、11、14-十七碳三烯基、顺-10-十九碳烯基、顺-12-二十碳烯基、乙炔基、2-丙炔基、1-甲基-2-丙炔基、2-甲基-2-丙炔基、2-乙基-2-丙炔基、2-丁炔基、1-甲基-2-丁炔基、2-甲基-2-丁炔基、1-乙基-2-丁炔基、3-丁炔基、1-甲基-3-丁炔基、2-甲基-3-丁炔基、1-乙基-3-丁炔基、2-戊炔基、1-甲基-2-戊炔基、2-甲基-2-戊炔基、3-戊炔基、1-甲基-3-戊炔基、2-甲基-3-戊炔基、4-戊炔基、1-甲基-4-戊炔基、2-甲基-4-戊炔基、2-己炔基、3-己炔基、4-己炔基、5-己炔基等碳原子数2~21的直链或支链不饱和烷基;
甲氧基甲基、乙氧基甲基、甲氧基乙基、乙氧基乙基、三氟甲基、三氯甲基、二氟甲基、二氯甲基、二溴甲基、氟甲基、2,2,2-三氟乙基、2,2,2-三氯乙基、2-溴乙基、2-氯乙基、2-氟乙基、2-碘乙基、3-氯丙基、4-氟丁基、6-碘己基、2,2-二溴乙基、硝基甲基、二硝基甲基、1-硝基乙基、2-硝基乙基、1,2-二硝基乙基等用从碳原子数1~4的烷氧基、卤素(例如,氟、氯、溴、碘,优选的是氟或氯。以下相同。)和硝基组成的组中选出的取代基取代的碳原子数1~21的直链或支链烷基;
苄基、α-萘基甲基、β-萘基甲基、茚基甲基、菲基甲基、蒽基甲基、二苯基甲基、三苯基甲基、1-苯乙基、2-苯乙基、1-萘基乙基、2-萘基乙基、1-苯基丙基、2-苯基丙基、3-苯基丙基、1-萘基丙基、2-萘基丙基、3-萘基丙基、1-苯基丁基、2-苯基丁基、3-苯基丁基、4-苯基丁基、1-萘基丁基、2-萘基丁基、3-萘基丁基、4-萘基丁基、1-苯基戊基、2-苯基戊基、3-苯基戊基、4-苯基戊基、5-苯基戊基、1-萘基戊基、2-萘基戊基、3-萘基戊基、4-萘基戊基、5-萘基戊基、1-苯基己基、2-苯基己基、3-苯基己基、4-苯基己基、5-苯基己基、6-苯基己基、1-萘基己基、2-萘基己基、3-萘基己基、4-萘基己基、5-萘基己基、6-萘基己基等可用从碳原子数1~4的烷基、碳原子数1~4的烷氧基、卤素和硝基组成的组中选出的取代基取代的(碳原子数6~10的芳基)-(碳原子数1~21的烷基);
苯基、萘基、2-氟苯基、3-氟苯基、4-氟苯基、2-氯苯基、3-氯苯基、4-氯苯基、2-溴苯基、3-溴苯基、4-溴苯基、3,5-二氟苯基、2,5-二氟苯基、2,6-二氟苯基、2,4-二氟苯基、3,5-二溴苯基、2,5-二溴苯基、2,6-二氯苯基、2,4-二氯苯基、2,3,6-三氟苯基、2,3,4-三氟苯基、3,4,5-三氟苯基、2,5,6-三氟苯基、2,4,6-三氟苯基、2,3,6-三溴苯基、2,3,4-三溴苯基、3,4,5-三溴苯基、2,5,6-三氯苯基、2,4,6-三氯苯基、1-氟-2-萘基、2-氟-1-萘基、3-氟-1-萘基、1-氯-2-萘基、2-氯-1-萘基、3-溴-1-萘基、3,8-二氟-1-萘基、2,3-二氟-1-萘基、4,8-二氟-1-萘基、5,6-二氟-1-萘基、3,8-二氯-1-萘基、2,3-二氯-1-萘基、4,8-二溴-1-萘基、5,6-二溴-1-萘基、2,3,6-三氟-1-萘基、2,3,4-三氟-1-萘基、3,4,5-三氟-1-萘基、4,5,6-三氟-1-萘基、2,4,8-三氟-1-萘基、2-甲基苯基、3-甲基苯基、4-甲基苯基、2-乙基苯基、3-丙基苯基、4-乙基苯基、2-丁基苯基、3-戊基苯基、4-戊基苯基、3,5-二甲基苯基、2,5-二甲基苯基、2,6-二甲基苯基、2,4-二甲基苯基、3,5-二丁基苯基、2,5-二戊基苯基、2,6-二丙基甲基苯基、2,4-二丙基苯基、2,3,6-三甲基苯基、2,3,4-三甲基苯基、3,4,5-三甲基苯基、2,5,6-三甲基苯基、2,4,6-三甲基苯基、2,3,6-三丁基苯基、2,3,4-三戊基苯基、3,4,5-三丁基苯基、2,5,6-三丙基甲基苯基、2,4,6-三丙基苯基、1-甲基-2-萘基、2-甲基-1-萘基、3-甲基-1-萘基、1-乙基-2-萘基、2-丙基-1-萘基、3-丁基-1-萘基、3,8-二甲基-1-萘基、2,3-二甲基-1-萘基、4,8-二甲基-1-萘基、5,6-二甲基-1-萘基、3,8-二乙基-1-萘基、2,3-二丙基-1-萘基、4,8-二戊基-1-萘基、5,6-二丁基-1-萘基、2,3,6-三甲基-1-萘基、2,3,4-三甲基-1-萘基、3,4,5-三甲基-1-萘基、4,5,6-三甲基-1-萘基、2,4,8-三甲基-1-萘基、2-甲氧基苯基、3-甲氧基苯基、4-甲氧基苯基、2-乙氧基苯基、3-丙氧基苯基、4-乙氧基苯基、2-丁氧基苯基、3-戊氧基苯基、4-戊氧基苯基、3,5-二甲氧基苯基、2,5-二甲氧基苯基、2,6-二甲氧基苯基、2,4-二甲氧基苯基、3,5-二丁氧基苯基、2,5-二戊氧基苯基、2,6-二丙氧基甲氧基苯基、2,4-二丙氧基苯基、2,3,6-三甲氧基苯基、2,3,4-三甲氧基苯基、3,4,5-三甲氧基苯基、2,5,6-三甲氧基苯基、2,4,6-三甲氧基苯基、2,3,6-三丁氧基苯基、2,3,4-三戊氧基苯基、3,4,5-三丁氧基苯基、2,5,6-三丙氧基苯基、2,4,6-三丙氧基苯基、1-甲氧基-2-萘基、2-甲氧基-1-萘基、3-甲氧基-1-萘基、1-乙氧基-2-萘基、2-丙氧基-1-萘基、3-丁氧基-1-萘基、3,8-二甲氧基-1-萘基、2,3-二甲氧基-1-萘基、4,8-二甲氧基-1-萘基、5,6-二甲氧基-1-萘基、3,8-二乙氧基-1-萘基、2,3-二丙氧基-1-萘基、4,8-二戊氧基-1-萘基、5,6-二丁氧基-1-萘基、2,3,6-三甲氧基-1-萘基、2,3,4-三甲氧基-1-萘基、3,4,5-三甲氧基-1-萘基、4,5,6-三甲氧基-1-萘基、2,4,8-三甲氧基-1-萘基、2-硝基苯基、3-硝基苯基、4-硝基苯基、3,5-二硝基苯基、2,5-二硝基苯基、2,6-二硝基苯基、2,4-二硝基苯基、2,3,6-三硝基苯基、2,3,4-三硝基苯基、3,4,5-三硝基苯基、2,5,6-三硝基苯基、2,4,6-三硝基苯基、1-硝基-2-萘基、2-硝基-1-萘基、3-硝基-1-萘基、3,8-二硝基-1-萘基、2,3-二硝基-1-萘基、4,8-二硝基-1-萘基、5,6-二硝基-1-萘基、2,3,6-三硝基-1-萘基、2,3,4-三硝基-1-萘基、3,4,5-三硝基-1-萘基、4,5,6-三硝基-1-萘基、2,4,8-三硝基-1-萘基等可用从碳原子数1~4的烷基、碳原子数1~4的烷氧基、卤素和硝基组成的组选出的取代基取代的碳原子数6~10的芳基。
其中优选的是,碳原子数1~21的烷基;具有1~3个的不饱和键的碳原子数2~21的不饱和烷基;具有1~4个的从碳原子数1~4的烷氧基、卤素和硝基组成的组选出的取代基的碳原子数1~21的烷基;具有1~3个的碳原子数6~10的芳基作为取代基的碳原子数1~21的烷基,其中芳基可有1~4个从碳原子数1~4的烷基、碳原子数1~4的烷氧基、卤素和硝基组成的组中选出的取代基;或可具有1~4个从碳原子数1~4的烷基、碳原子数1~4的烷氧基、卤素和硝基组成的组选出的取代基的碳原子数6~10个的芳基;
更优选的是,碳原子数6~20个的烷基;具有1~3个双键的碳原子数10~20的链烯基;具有1个三键的碳原子数3~5的炔基;具有1个碳原子数1~4的烷氧基作为取代基的碳原子数1~4个的烷基;具有1~2个苯基作为取代基的碳原子数1~4个的烷基;所述苯基可以具有1~2个从由碳原子数1~2的烷基、碳原子数1~4的烷氧基、氟或氯组成的组选出的取代基。
最优选的是,碳原子数6~20的烷基或具有1~3个双键的碳原子数10~20的链烯基。
另外,通式(I)所示化合物中,存在多个可结合酯残基或醚残基的羟基。即,在氧杂环戊环(オキソラン环)的2位的羟基(R3是羟基时),二氢吡喃环的3位和4位的羟基。在通式(I)所示化合物的酯或醚衍生物中,酯残基或醚残基可与这些羟基任意组合,形成多个,它们可相同或不同的酯基或醚基。
通式(I)所示化合物的药理上容许的酯衍生物中,优选具有将上述羟基中的1个或2个转化为酯残基的化合物,更优选具有将オキソラン环的2位羟基和二氢吡喃环3位的羟基中的一个转化为酯残基的化合物,最优选具有只将オキソラン环的2位羟基转化为酯残基的化合物。
通式(I)所示化合物的药理上容许的醚衍生物中,优选具有将上述羟基中的1个或2个转化为醚残基的化合物,更优选具有将オキソラン环的2位羟基和二氢吡喃环3位的羟基中的一个转化为醚残基的化合物,最优选具有只将オキソラン环的2位羟基转化为醚残基的化合物。
作为药理上容许的N-烷基衍生物的烷基残基,可列举例如,前述碳原子数1~21的直链或支链烷基;前述碳原子数2~21的直链或支链不饱和烷基;乙酰氧甲基、丙酰氧甲基、丁酰氧甲基、戊酰氧甲基、新戊酰氧、己酰氧甲基、辛酰氧甲基、癸酰氧甲基、十二烷酰氧甲基、十四烷酰氧甲基、十六烷酰氧甲基、十八烷酰氧甲基、1-(乙酰氧)乙基、1-(丙酰氧)乙基、1-(丁酰氧)乙基、1-(戊酰氧)乙基、1-(己酰氧)乙基、1-(辛酰氧)乙基、1-(癸酰氧)乙基、1-(十二烷酰氧)乙基、1-(十四烷酰氧)乙基、1-(十六烷酰氧)乙基、1-(十八烷酰氧)乙基等1-(碳原子数2~20的烷酰氧基)-碳原子数1~3的烷基;甲氧羰基氧甲基、乙氧羰基氧甲基、丙氧羰基氧甲基、异丙氧羰基氧甲基、丁氧羰基氧甲基、异丁氧羰基氧甲基、仲丁氧羰基氧甲基、叔丁氧羰基氧甲基、戊氧羰基氧甲基、2-戊氧羰基氧甲基、3-戊氧羰基氧甲基、异戊氧羰基氧甲基、新戊氧羰基氧甲基、环戊氧羰基氧甲基、己氧羰基氧甲基、2-己氧羰基氧甲基、3-己氧羰基氧甲基、异己氧羰基氧甲基、环己氧羰基氧甲基、庚氧羰基氧甲基、辛氧羰基氧甲基、癸氧羰基氧甲基、十二烷氧羰基氧甲基、十四烷氧羰基氧甲基、十六烷氧羰基氧甲基、十八烷氧羰基氧甲基、1-(甲氧羰基氧)乙基、1-(乙氧羰基氧)乙基、1-(丙氧羰基氧)乙基、1-(异丙氧羰基氧)乙基、1-(丁氧羰基氧)乙基、1-(异丁氧羰基氧)乙基、1-(仲丁氧羰基氧)乙基、1-(叔丁氧羰基氧)乙基、1-(戊氧羰基氧)乙基、1-(2-戊氧羰基氧)乙基、1-(3-戊氧羰基氧)乙基、1-(异戊氧羰基氧)乙基、1-(新戊氧羰基氧)乙基、1-(环戊氧羰基氧)乙基、1-(己氧羰基氧)乙基、1-(2-己氧羰基氧)乙基、1-(3-己氧羰基氧)乙基、1-(异己氧羰基氧)乙基、1-(环己氧羰基氧)乙基、1-(庚氧羰基氧)乙基、1-(辛氧羰基氧)乙基、1-(癸氧羰基氧)乙基、1-(十二烷氧羰基氧)乙基、1-(十四烷氧羰基氧)乙基、1-(十六烷氧羰基氧)乙基、1-(十八烷氧羰基氧)乙基等1-(碳原子数1~20的烷氧羰基氧)-碳原子数1~3的烷基;(5-甲基-2-氧代-1,3-二氧杂戊环-4-基)甲基、1-(5-甲基-2-氧代-1,3-二氧杂戊环-4-基)乙基、(5-苯基-2-氧代-1,3-二氧杂戊环-4-基)甲基等1-[5-(碳原子数1~6的烷基或苯基)-2-氧代-1,3-二氧杂戊环-4-基]碳原子数1~6的烷基。
其中优选的是,1-(碳原子数2~20的烷酰氧)-碳原子数1~3的烷基或1-(碳原子数1~20的烷氧羰基氧)-碳原子数1~3的烷基。被这些基团改性的衍生物,对生物体内给药时,可被化学或酶水解,还原为母体化合物(I)。
通式(I)所示化合物、其药理上可接受的酯、醚或N-烷基衍生物的“药理上容许的盐”是指,没有显著的毒性,可作为药物使用的盐。
在通式(I)所示化合物、其药理上可接受的酯、醚或N-烷基衍生物具有氨基等碱性基团时,可按照常法通过用酸处理,转变成相应的药理上容许的酸加成盐。作为这样的酸加成盐,可列举例如,盐酸盐、氢溴酸盐、硫酸盐、磷酸盐等无机盐;醋酸盐、苯甲酸盐、草酸盐、马来酸盐、富马酸盐、酒石酸盐、柠檬酸盐等有机酸盐;或甲磺酸盐、苯磺酸盐、对甲苯磺酸盐等磺酸盐的加成盐。
在通式(I)化合物、其药理上可接受的酯、醚或N-烷基衍生物具有羧基、磷酸等酸性基团时,可按照常法通过用碱处理,转变成相应的药理上容许的碱加成盐。作为这样的碱加成盐,可列举例如,钠盐、钾盐、锂盐等碱金属盐;钙盐、镁盐等碱土金属盐;铝盐、铁盐、锌盐、铜盐、镍盐、钴盐等金属盐;或铵盐、三乙基铵盐等季铵盐。
另外,通式(I)所示化合物、其药理上可接受的酯、醚或N-烷基衍生物,通过放置在大气中,有吸收水分、带有吸附水,成为水合物的情况,这样的盐也包含在本发明中。
另外,通式(I)所示化合物、其药理上可接受的酯、醚或N-烷基衍生物,有吸收其他种溶剂,成为溶剂化物的情况,这样的盐也包含在本发明中。
通式(I)所示化合物、其药理上可接受的酯、醚或N-烷基衍生物,由于在分子内有不对称碳,因此分别存在作为R构型、S构型的立体异构体,其单独的、或其任意比例的混合物都包含在本发明中,优选的是具有下式(I’)所示的立体构型的化合物。
在下面表1~3中具体列举本发明的通式(I)所示化合物、其药理上可接受的酯、醚或N-烷基衍生物。但是本发明并不限于所列举的化合物。
[表1]化合物编号      R1   X1     R2       X2      R3       R6       R71         Ph    NH       H         NH       H          H         H2         Ph    NH       H         NH       OH         H         H3         Ph         NH       H        NH       OA6         H        H4         Ph         NH       H        NH       OA8         H        H5         Ph         NH       H        NH       OA9         H        H6         Ph         NH       H        NH       OA10        H        H7         Ph         NH       H        NH       OA12        H        H8         Ph         NH       H        NH       OA14        H        H9         Ph         NH       H        NH       OA16        H        H10        Ph         NH       H        NH       OH          H        A611        Ph         NH       H        NH       OH          H        A812        Ph         NH       H        NH       OH          H        A913        Ph         NH       H        NH       OH          H        A1014        Ph         NH       H        NH       OH          H        A1215        Ph         NH       H        NH       OH          H        A1416        Ph         NH       H        NH       OH          H        A1617        Ph         NH       H        NH       OH          A6       A618        Ph         NH       H        NH       OH          A8       A819        Ph         NH       H        NH       OH          A10      A1020        Ph         NH       H        NH       OA2         A2       A221        Ph         NH       H        NH       OA3         A3       A322        Ph         NH       H        NH       OA4         A4       A423        Ph         NH       H        NH       OC6         H        H24        Ph         NH       H        NH       OC7         H        H25        Ph         NH       H        NH       OC8         H        H26        Ph         NH       H        NH       OC10        H        H27        Ph         NH       H        NH       OC11        H        H28        Ph         NH       H        NH       OC12        H        H29        Ph         NH       H        NH       OC14        H        H30        Ph         NH       H        NH       OC16        H        H31        Ph         NH       H        NH       C6CO3      H        H32     Ph         NH            H             NH           C7CO3    H     H33     Ph         NH            H             NH           C8CO3    H     H34     Ph         NH            H             NH           C9CO3    H     H35     Ph         NH            H             NH           C10CO3   H     H36     Ph         NH            H             NH           C12CO3   H     H37     Ph         NH            H             NH           C16CO3   H     H38     Ph         NH            C8            NH           OH        H     H39     Ph         NH            C9            NH           OH        H     H40     Ph         NH            C10           NH           OH        H     H41     Ph         NH            C12           NH           OH        H     H42     Ph         NH            C16           NH           OH        H     H43     Ph         NH            F1            NH           OH        H     H44     Ph         NH            F2            NH           OH        H     H45     Ph         NH            F3            NH           OH        H     H46     Ph         NH            F4            NH           OH        H     H47     Ph         NH            F5            NH           OH        H     H48     Ph         NH            F6            NH           OH        H     H49     Ph         NH            F7            NH           OH        H     H50     Ph         NH            F8            NH           OH        H     H51     Ph         NH            F9            NH           OH        H     H52     Ph         NH            F10           NH           OH        H     H53     Ph         NH            Ph            NH           OH        H     H54     Ph         NH            Bn            NH           OH        H     H55     Ph         NH            Pe            NH           OH        H     H56     Ph         NH            C12           NMe          OH        H     H57     Ph         NH            C12           NEt          OH        H     H58     Ph         NH            C12           NPr          OH        H     H59     Ph         NH            (CH2)3     N            OH        H     H60     Ph         NH            (CH2)4     N            OH        H     H61   Ph              NH        (CH2)5N        OH           H          H62   Ph              NH         C12    O         OH           H          H63   Ph              NH         Ph     O         OH           H          H64   Ph              NH         C12    S         OH           H          H65   Ph              NH         Ph     S         OH           H          H66   Ph              NMe        H     NH         OH           H          H67   Ph              NEt        H     NH         OH           H          H68   Ph              NPr        H     NH         OH           H          H69   Ph              O          H     NH         OH           H          H70   Ph              S          H     NH         OH           H          H71   4-Me-Ph         NH         H     NH         H            H          H72   4-Me-Ph         NH         H     NH         OH           H          H73   4-Me-Ph         NH         H     NH         OA6          H          H74   4-Me-Ph         NH         H     NH         OA8          H          H75   4-Me-Ph         NH         H     NH         OA9          H          H76   4-Me-Ph         NH         H     NH         OA10         H          H77   4-Me-Ph         NH         H     NH         OA12         H          H78   4-Me-Ph         NH         H     NH         OA14         H          H79   4-Me-Ph         NH         H     NH         OA16         H          H80   4-Me-Ph         NH         H     NH         OH           H          A681   4-Me-Ph         NH         H     NH         OH           H          A882   4-Me-Ph         NH         H     NH         OH           H          A983   4-Me-Ph         NH         H     NH         OH           H          A1084   4-Me-Ph         NH         H     NH         OH           H          A1285   4-Me-Ph         NH         H     NH         OH           H          A1486   4-Me-Ph         NH         H     NH         OH           H          A1687   4-Me-Ph         NH         H     NH         OH           A6         A688   4-Me-Ph         NH         H     NH         OH           A8         A889   4-Me-Ph         NH         H     NH         OH           A10        A1090          4-Me-Ph       NH          H     NH         OA2     A2         A291          4-Me-Ph       NH          H     NH         OA3     A3         A392          4-Me-Ph       NH          H     NH         OA4     A4         A493          4-Me-Ph       NH          H     NH         OC6     H          H94          4-Me-Ph       NH          H     NH         OC7     H          H95          4-Me-Ph       NH          H     NH         OC8     H          H96          4-Me-Ph       NH          H     NH         OC10    H          H97          4-Me-Ph       NH          H     NH         OC11    H          H98          4-Me-Ph       NH          H     NH         OC12    H          H99          4-Me-Ph       NH          H     NH         OC14    H          H100         4-Me-Ph       NH          H     NH         OC16    H          H101         4-Me-Ph       NH          H     NH         C6CO3  H          H102         4-Me-Ph       NH          H     NH         C7CO3  H          H103         4-Me-Ph       NH          H     NH         C8CO3  H          H104         4-Me-Ph       NH          H     NH         C9CO3  H          H105         4-Me-Ph       NH          H     NH         C10CO3 H          H106         4-Me-Ph       NH          H     NH         C12CO3 H          H107         4-Me-Ph       NH          H     NH         C16CO3 H          H108         4-Me-Ph       NH          C8    NH         OH      H          H109         4-Me-Ph       NH          C9    NH         OH      H          H110         4-Me-Ph       NH          C10   NH         OH      H          H111         4-Me-Ph       NH          C12   NH         OH      H          H112         4-Me-Ph       NH          C16   NH         OH      H          H113         4-Me-Ph       NH          F1    NH         OH      H          H114         4-Me-Ph       NH          F2    NH         OH      H          H115         4-Me-Ph       NH          F3    NH         OH      H          H116         4-Me-Ph       NH          F4    NH         OH      H          H117         4-Me-Ph       NH          F5    NH         OH      H          H118         4-Me-Ph       NH          F6    NH         OH      H          H119        4-Me-Ph       NH         F7           NH        OH          H   H120        4-Me-Ph       NH         F8           NH        OH          H   H121        4-Me-Ph       NH         F9           NH        OH          H   H122        4-Me-Ph       NH         F10          NH        OH          H   H123        4-Me-Ph       NH         Ph           NH        OH          H   H124        4-Me-Ph       NH         Bn           NH        OH          H   H125        4-Me-Ph       NH         Pe           NH        OH          H   H126        4-Me-Ph       NH         C12          NMe       OH          H   H127        4-Me-Ph       NH         C12          NEt       OH          H   H128        4-Me-Ph       NH         C12          NPr       OH          H   H129        4-Me-Ph       NH         (CH2)3    N         OH          H   H130        4-Me-Ph       NH         (CH2)4    N         OH          H   H131        4-Me-Ph       NH         (CH2)5    N         OH          H   H132        4-Me-Ph       NH         C12          O         OH          H   H133        4-Me-Ph       NH         Ph           O         OH          H   H134        4-Me-Ph       NH         C12          S         OH          H   H135        4-Me-Ph       NH         Ph           S         OH          H   H136        4-Me-Ph       NMe        H            NH        OH          H   H137        4-Me-Ph       NEt        H            NH        OH          H   H138        4-Me-Ph       NPr        H            NH        OH          H   H139        4-Me-Ph       O          H            NH        OH          H   H140        4-Me-Ph       S          H            NH        OH          H   H141        4-Et-Ph       NH         H            NH        H           H   H142        4-Et-Ph       NH         H            NH        OH          H   H143        4-Et-Ph       NH         H            NH        OA6         H   H144        4-Et-Ph       NH         H            NH        OA8         H   H145        4-Et-Ph       NH         H            NH        OA9         H   H146        4-Et-Ph       NH         H            NH        OA10        H   H147        4-Et-Ph       NH         H            NH        OA12        H   H148        4-Et-Ph        NH        H     NH        OA14         H          H149        4-Et-Ph        NH        H     NH        OA16         H          H150        4-Et-Ph        NH        H     NH        OH           H          A6151        4-Et-Ph        NH        H     NH        OH           H          A8152        4-Et-Ph        NH        H     NH        OH           H          A9153        4-Et-Ph        NH        H     NH        OH           H          A10154        4-Et-Ph        NH        H     NH        OH           H          A12155        4-Et-Ph        NH        H     NH        OH           H          A14156        4-Et-Ph        NH        H     NH        OH           H          A16157        4-Et-Ph        NH        H     NH        OH           A6         A6158        4-Et-Ph        NH        H     NH        OH           A8         A8159        4-Et-Ph        NH        H     NH        OH           A10        A10160        4-Et-Ph        NH        H     NH        OA2          A2         A2161        4-Et-Ph        NH        H     NH        OA3          A3         A3162        4-Et-Ph        NH        H     NH        OA4          A4         A4163        4-Et-Ph        NH        H     NH        OC6          H          H164        4-Et-Ph        NH        H     NH        OC7          H          H165        4-Et-Ph        NH        H     NH        OC8          H          H166        4-Et-Ph        NH        H     NH        OC10         H          H167        4-Et-Ph        NH        H     NH        OC11         H          H168        4-Et-Ph        NH        H     NH        OC12         H          H169        4-Et-Ph        NH        H     NH        OC14         H          H170        4-Et-Ph        NH        H     NH        OC16         H          H171        4-Et-Ph        NH        H     NH        C6CO3       H          H172        4-Et-Ph        NH        H     NH        C7CO3       H          H173        4-Et-Ph        NH        H     NH        C8CO3       H          H174        4-Et-Ph        NH        H     NH        C9CO3       H          H175        4-Et-Ph        NH        H     NH        C10CO3      H          H176        4-Et-Ph        NH        H     NH        C12CO3      H          H177  4-Et-Ph        NH        H            NH       C16CO3       H          H178  4-Et-Ph        NH        C8           NH       OH            H          H179  4-Et-Ph        NH        C9           NH       OH            H          H180  4-Et-Ph        NH        C10          NH       OH            H          H181  4-Et-Ph        NH        C12          NH       OH            H          H182  4-Et-Ph        NH        C16          NH       OH            H          H183  4-Et-Ph        NH        F1           NH       OH            H          H184  4-Et-Ph        NH        F2           NH       OH            H          H185  4-Et-Ph        NH        F3           NH       OH            H          H186  4-Et-Ph        NH        F4           NH       OH            H          H187  4-Et-Ph        NH        F5           NH       OH            H          H188  4-Et-Ph        NH        F6           NH       OH            H          H189  4-Et-Ph        NH        F7           NH       OH            H          H190  4-Et-Ph        NH        F8           NH       OH            H          H191  4-Et-Ph        NH        F9           NH       OH            H          H192  4-Et-Ph        NH        F10          NH       OH            H          H193  4-Et-Ph        NH        Ph           NH       OH            H          H194  4-Et-Ph        NH        Bn           NH       OH            H          H195  4-Et-Ph        NH        Pe           NH       OH            H          H196  4-Et-Ph        NH        C12          NMe      OH            H          H197  4-Et-Ph        NH        C12          NEt      OH            H          H198  4-Et-Ph        NH        C12          NPr      OH            H          H199  4-Et-Ph        NH        (CH2)3    N        OH            H          H200  4-Et-Ph        NH        (CH2)4    N        OH            H          H201  4-Et-Ph        NH        (CH2)5    N        OH            H          H202  4-Et-Ph        NH        C12          O        OH            H          H203  4-Et-Ph        NH        Ph           O        OH            H          H204  4-Et-Ph        NH        C12          S        OH            H          H205  4-Et-Ph        NH        Ph           S        OH            H          H206      4-Et-Ph       NMe           H          NH      OH         H        H207      4-Et-Ph       NEt           H          NH      OH         H        H208      4-Et-Ph       NPr           H          NH      OH         H        H209      4-Et-Ph       O             H          NH      OH         H        H210      4-Et-Ph       S             H          NH      OH         H        H211      4-Pr-Ph       NH            H          NH      H          H        H212      4-Pr-Ph       NH            H          NH      OH         H        H213      4-Pr-Ph       NH            H          NH      OA6        H        H214      4-Pr-Ph       NH            H          NH      OA8        H        H215      4-Pr-Ph       NH            H          NH      OA9        H        H216      4-Pr-Ph       NH            H          NH      OA10       H        H217      4-Pr-Ph       NH            H          NH      OA12       H        H218      4-Pr-Ph       NH            H          NH      OA14       H        H219      4-Pr-Ph       NH            H          NH      OA16       H        H220      4-Pr-Ph       NH            H          NH      OH         H        A6221      4-Pr-Ph       NH            H          NH      OH         H        A8222      4-Pr-Ph       NH            H          NH      OH         H        A9223      4-Pr-Ph       NH            H          NH      OH         H        A10224      4-Pr-Ph       NH            H          NH      OH         H        A12225      4-Pr-Ph       NH            H          NH      OH         H        A14226      4-Pr-Ph       NH            H          NH      OH         H        A16227      4-Pr-Ph       NH            H          NH      OH         A6       A6228      4-Pr-Ph       NH            H          NH      OH         A8       A8229      4-Pr-Ph       NH            H          NH      OH         A10      A10230      4-Pr-Ph       NH            H          NH      OA2        A2       A2231      4-Pr-Ph       NH            H          NH      OA3        A3       A3232      4-Pr-Ph       NH            H          NH      OA4        A4       A4233      4-Pr-Ph       NH            H          NH      OC6        H        H234      4-Pr-Ph       NH            H          NH      OC7        H        H235        4-Pr-Ph        NH       H           NH            OC8         H   H236        4-Pr-Ph        NH       H           NH            OC10        H   H237        4-Pr-Ph        NH       H           NH            OC11        H   H238        4-Pr-Ph        NH       H           NH            OC12        H   H239        4-Pr-Ph        NH       H           NH            OC14        H   H240        4-Pr-Ph        NH       H           NH            OC16        H   H241        4-Pr-Ph        NH       H           NH            C6CO3      H   H242        4-Pr-Ph        NH       H           NH            C7CO3      H   H243        4-Pr-Ph        NH       H           NH            C8CO3      H   H244        4-Pr-Ph        NH       H           NH            C9CO3      H   H245        4-Pr-Ph        NH       H           NH            C10CO3     H   H246        4-Pr-Ph        NH       H           NH            C12CO3     H   H247        4-Pr-Ph        NH       H           NH            C16CO3     H   H248        4-Pr-Ph        NH       C8          NH            OH          H   H249        4-Pr-Ph        NH       C9          NH            OH          H   H250        4-Pr-Ph        NH       C10         NH            OH          H   H251        4-Pr-Ph        NH       C12         NH            OH          H   H252        4-Pr-Ph        NH       C16         NH            OH          H   H253        4-Pr-Ph        NH       F1          NH            OH          H   H254        4-Pr-Ph        NH       F2          NH            OH          H   H255        4-Pr-Ph        NH       F3          NH            OH          H   H256        4-Pr-Ph        NH       F4          NH            OH          H   H257        4-Pr-Ph        NH       F5          NH            OH          H   H258        4-Pr-Ph        NH       F6          NH            OH          H   H259        4-Pr-Ph        NH       F7          NH            OH          H   H260        4-Pr-Ph        NH       F8          NH            OH          H   H261        4-Pr-Ph        NH       F9          NH            OH          H   H262        4-Pr-Ph        NH       F10         NH            OH          H   H263        4-Pr-Ph        NH       Ph          NH            OH          H   H264      4-Pr-Ph        NH          Bn        NH      OH        H         H265      4-Pr-Ph        NH          Pe        NH      OH        H         H266      4-Pr-Ph        NH          C12       NMe     OH        H         H267      4-Pr-Ph        NH          C12       NEt     OH        H         H268      4-Pr-Ph        NH          C12       NPr     OH        H         H269      4-Pr-Ph        NH          (CH2)3 N       OH        H         H270      4-Pr-Ph        NH          (CH2)4 N       OH        H         H271      4-Pr-Ph        NH          (CH2)5 N       OH        H         H272      4-Pr-Ph        NH          C12       O       OH        H         H273      4-Pr-Ph        NH          Ph        O       OH        H         H274      4-Pr-Ph        NH          C12       S       OH        H         H275      4-Pr-Ph        NH          Ph        S       OH        H         H276      4-Pr-Ph        NMe         H         NH      OH        H         H277      4-Pr-Ph        NEt         H         NH      OH        H         H278      4-Pr-Ph        NPr         H         NH      OH        H         H279      4-Pr-Ph        O           H         NH      OH        H         H280      4-Pr-Ph        S           H         NH      OH        H         H281      4-iPr-Ph       NH          H         NH      H         H         H282      4-iPr-Ph       NH          H         NH      OH        H         H283      4-iPr-Ph       NH          H         NH      OA6       H         H284      4-iPr-Ph       NH          H         NH      OA8       H         H285      4-iPr-Ph       NH          H         NH      OA9       H         H286      4-iPr-Ph       NH          H         NH      OA10      H         H287      4-iPr-Ph       NH          H         NH      OA12      H         H288      4-iPr-Ph       NH          H         NH      OA14      H         H289      4-iPr-Ph       NH          H         NH      OA16      H         H290      4-iPr-Ph       NH          H         NH      OH        H         A6291      4-iPr-Ph       NH          H         NH      OH        H         A8292      4-iPr-Ph       NH          H         NH      OH        H         A9293      4-iPr-Ph       NH       H           NH      OH          H       A10294      4-iPr-Ph       NH       H           NH      OH          H       A12295      4-iPr-Ph       NH       H           NH      OH          H       A14296      4-iPr-Ph       NH       H           NH      OH          H       A16297      4-iPr-Ph       NH       H           NH      OH          A6      A6298      4-iPr-Ph       NH       H           NH      OH          A8      A8299      4-iPr-Ph       NH       H           NH      OH          A10     A10300      4-iPr-Ph       NH       H           NH      OA2         A2      A2301      4-iPr-Ph       NH       H           NH      OA3         A3      A3302      4-iPr-Ph       NH       H           NH      OA4         A4      A4303      4-iPr-Ph       NH       H           NH      OC6         H       H304      4-iPr-Ph       NH       H           NH      OC7         H       H305      4-iPr-Ph       NH       H           NH      OC8         H       H306      4-iPr-Ph       NH       H           NH      OC10        H       H307      4-iPr-Ph       NH       H           NH      OC11        H       H308      4-iPr-Ph       NH       H           NH      OC12        H       H309      4-iPr-Ph       NH       H           NH      OC14        H       H310      4-iPr-Ph       NH       H           NH      OC16        H       H311      4-iPr-Ph       NH       H           NH      C6CO3      H       H312      4-iPr-Ph       NH       H           NH      C7CO3      H       H313      4-iPr-Ph       NH       H           NH      C8CO3      H       H314      4-iPr-Ph       NH       H           NH      C9CO3      H       H315      4-iPr-Ph       NH       H           NH      C10CO3     H       H316      4-iPr-Ph       NH       H           NH      C12CO3     H       H317      4-iPr-Ph       NH       H           NH      C16CO3     H       H318      4-iPr-Ph       NH       C8          NH      OH          H       H319      4-iPr-Ph       NH       C9          NH      OH          H       H320      4-iPr-Ph       NH       C10         NH      OH          H       H321      4-iPr-Ph       NH       C12         NH      OH          H       H322         4-iPr-Ph        NH    C16          NH         OH           H    H323         4-iPr-Ph        NH    F1           NH         OH           H    H324         4-iPr-Ph        NH    F2           NH         OH           H    H325         4-iPr-Ph        NH    F3           NH         OH           H    H326         4-iPr-Ph        NH    F4           NH         OH           H    H327         4-iPr-Ph        NH    F5           NH         OH           H    H328         4-iPr-Ph        NH    F6           NH         OH           H    H329         4-iPr-Ph        NH    F7           NH         OH           H    H330         4-iPr-Ph        NH    F8           NH         OH           H    H331         4-iPr-Ph        NH    F9           NH         OH           H    H332         4-iPr-Ph        NH    F10          NH         OH           H    H333         4-iPr-Ph        NH    Ph           NH         OH           H    H334         4-iPr-Ph        NH    Bn           NH         OH           H    H335         4-iPr-Ph        NH    Pe           NH         OH           H    H336         4-iPr-Ph        NH    C12          NMe        OH           H    H337         4-iPr-Ph        NH    C12          NEt        OH           H    H338         4-iPr-Ph        NH    C12          NPr        OH           H    H339         4-iPr-Ph        NH    (CH2)3    N          OH           H    H340         4-iPr-Ph        NH    (CH2)4    N          OH           H    H341         4-iPr-Ph        NH    (CH2)5    N          OH           H    H342         4-iPr-Ph        NH    C12          O          OH           H    H343         4-iPr-Ph        NH    Ph           O          OH           H    H344         4-iPr-Ph        NH    C12          S          OH           H    H345         4-iPr-Ph        NH    Ph           S          OH           H    H346         4-iPr-Ph        NMe   H            NH         OH           H    H347         4-iPr-Ph        NEt   H            NH         OH           H    H348         4-iPr-Ph        NPr   H            NH         OH           H    H349         4-iPr-Ph        O     H            NH         OH           H    H350         4-iPr-Ph        S     H            NH         OH           H    H351         4-Bu-Ph         NH   H      NH        H            H          H352         4-Bu-Ph         NH   H      NH       OH            H          H353         4-Bu-Ph         NH   H      NH       OA6           H          H354         4-Bu-Ph         NH   H      NH       OA8           H          H355         4-Bu-Ph         NH   H      NH       OA9           H          H356         4-Bu-Ph         NH   H      NH       OA10          H          H357         4-Bu-Ph         NH   H      NH       OA12          H          H358         4-Bu-Ph         NH   H      NH       OA14          H          H359         4-Bu-Ph         NH   H      NH       OA16          H          H360         4-Bu-Ph         NH   H      NH       OH            H          A6361         4-Bu-Ph         NH   H      NH       OH            H          A8362         4-Bu-Ph         NH   H      NH       OH            H          A9363         4-Bu-Ph         NH   H      NH       OH            H          A10364         4-Bu-Ph         NH   H      NH       OH            H          A12365         4-Bu-Ph         NH   H      NH       OH            H          A14366         4-Bu-Ph         NH   H      NH       OH            H          A16367         4-Bu-Ph         NH   H      NH       OH            A6         A6368         4-Bu-Ph         NH   H      NH       OH            A8         A8369         4-Bu-Ph         NH   H      NH       OH            A10        A10370         4-Bu-Ph         NH   H      NH       OA2           A2         A2371         4-Bu-Ph         NH   H      NH       OA3           A3         A3372         4-Bu-Ph         NH   H      NH       OA4           A4         A4373         4-Bu-Ph         NH   H      NH       OC6           H          H374         4-Bu-Ph         NH   H      NH       OC7           H          H375         4-Bu-Ph         NH   H      NH       OC8           H          H376         4-Bu-Ph         NH   H      NH       OC10          H          H377         4-Bu-Ph         NH   H      NH       OC11          H          H378         4-Bu-Ph         NH   H      NH       OC12          H          H379         4-Bu-Ph         NH   H      NH       OC14          H          H380  4-Bu-Ph       NH      H          NH        OC16          H         H381  4-Bu-Ph       NH      H          NH        C6CO3        H         H382  4-Bu-Ph       NH      H          NH        C7CO3        H         H383  4-Bu-Ph       NH      H          NH        C8CO3        H         H384  4-Bu-Ph       NH      H          NH        C9CO3        H         H385  4-Bu-Ph       NH      H          NH        C1OCO3       H         H386  4-Bu-Ph       NH      H          NH        C12CO3       H         H387  4-Bu-Ph       NH      H          NH        C16CO3       H         H388  4-Bu-Ph       NH      C8         NH        OH            H         H389  4-Bu-Ph       NH      C9         NH        OH            H         H390  4-Bu-Ph       NH      C10        NH        OH            H         H391  4-Bu-Ph       NH      C12        NH        OH            H         H392  4-Bu-Ph       NH      C16        NH        OHH           H         H393  4-Bu-Ph       NH      F1         NH        OH            H         H394  4-Bu-Ph       NH      F2         NH        OH            H         H395  4-Bu-Ph       NH      F3         NH        OH            H         H396  4-Bu-Ph       NH      F4         NH        OH            H         H397  4-Bu-Ph       NH      F5         NH        OH            H         H398  4-Bu-Ph       NH      F6         NH        OH            H         H399  4-Bu-Ph       NH      F7         NH        OH            H         H400  4-Bu-Ph       NH      F8         NH        OH            H         H401  4-Bu-Ph       NH      F9         NH        OH            H         H402  4-Bu-Ph       NH      F10        NH        OH            H         H403  4-Bu-Ph       NH      Ph         NH        OH            H         H404  4-Bu-Ph       NH      Bn         NH        OH            H         H405  4-Bu-Ph       NH      Pe         NH        OH            H         H406  4-Bu-Ph       NH      C12        NMe       OH            H         H407  4-Bu-Ph       NH      C12        NEt       OH            H         H408  4-Bu-Ph       NH      C12        NPr       OH            H         H409  4-Bu-Ph         NH    (CH2)3   N          OH           H          H410  4-Bu-Ph         NH    (CH2)4   N          OH           H          H411  4-Bu-Ph         NH    (CH2)5   N          OH           H          H412  4-Bu-Ph         NH    C12         O          OH           H          H413  4-Bu-Ph         NH    Ph          O          OH           H          H414  4-Bu-Ph         NH    C12         S          OH           H          H415  4-Bu-Ph         NH    Ph          S          OH           H          H416  4-Bu-Ph         NMe   H           NH         OH           H          H417  4-Bu-Ph         NEt   H           NH         OH           H          H418  4-Bu-Ph         NPr   H           NH         OH           H          H419  4-Bu-Ph         O     H           NH         OH           H          H420  4-Bu-Ph         S     H           NH         OH           H          H421  4-tBu-Ph        NH    H           NH         H            H          H422  4-tBu-Ph        NH    H           NH         OH           H          H423  4-tBu-Ph        NH    H           NH         OA6          H          H424  4-tBu-Ph        NH    H           NH         OA8          H          H425  4-tBu-Ph        NH    H           NH         OA9          H          H426  4-tBu-Ph        NH    H           NH         OA10         H          H427  4-tBu-Ph        NH    H           NH         OA12         H          H428  4-tBu-Ph        NH    H           NH         OA14         H          H429  4-tBu-Ph        NH    H           NH         OA16         H          H430  4-tBu-Ph        NH    H           NH         OH           H          A6431  4-tBu-Ph        NH    H           NH         OH           H          A8432  4-tBu-Ph        NH    H           NH         OH           H          A9433  4-tBu-Ph        NH    H           NH         OH           H          A10434  4-tBu-Ph        NH    H           NH         OH           H          A12435  4-tBu-Ph        NH    H           NH         OH           H          A14436  4-tBu-Ph        NH    H           NH         OH           H          A16437  4-tBu-Ph        NH    H           NH         OH           A6         A6438  4-tBu-Ph       NH   H            NH          OH            A8         A8439  4-tBu-Ph       NH   H            NH          OH            A10        A10440  4-tBu-Ph       NH   H            NH          OA2           A2         A2441  4-tBu-Ph       NH   H            NH          OA3           A3         A3442  4-tBu-Ph       NH   H            NH          OA4           A4         A4443  4-tBu-Ph       NH   H            NH          OC6           H          H444  4-tBu-Ph       NH   H            NH          OC7           H          H445  4-tBu-Ph       NH   H            NH          OC8           H          H446  4-tBu-Ph       NH   H            NH          OC10          H          H447  4-tBu-Ph       NH   H            NH          OC11          H          H448  4-tBu-Ph       NH   H            NH          OC12          H          H449  4-tBu-Ph       NH   H            NH          OC14          H          H450  4-tBu-Ph       NH   H            NH          OC16          H          H451  4-tBu-Ph       NH   H            NH          C6CO3        H          H452  4-tBu-Ph       NH   H            NH          C7CO3        H          H453  4-tBu-Ph       NH   H            NH          C8CO3        H          H454  4-tBu-Ph       NH   H            NH          C9CO3        H          H455  4-tBu-Ph       NH   H            NH          C10CO3       H          H456  4-tBu-Ph       NH   H            NH          C12CO3       H          H457  4-tBu-Ph       NH   H            NH          C16CO3       H          H458  4-tBu-Ph       NH   C8           NH          OH            H          H459  4-tBu-Ph       NH   C9           NH          OH            H          H460  4-tBu-Ph       NH   C10          NH          OH            H          H461  4-tBu-Ph       NH   C12          NH          OH            H          H462  4-tBu-Ph       NH   C16          NH          OH            H          H463  4-tBu-Ph       NH   F1           NH          OH            H          H464  4-tBu-Ph       NH   F2           NH          OH            H          H465  4-tBu-Ph       NH   F3           NH          OH            H          H466  4-tBu-Ph       NH   F4           NH          OH            H          H467  4-tBu-Ph       NH          F5             NH      OH             H   H468  4-tBu-Ph       NH          F6             NH      OH             H   H469  4-tBu-Ph       NH          F7             NH      OH             H   H470  4-tBu-Ph       NH          F8             NH      OH             H   H471  4-tBu-Ph       NH          F9             NH      OH             H   H472  4-tBu-Ph       NH          F10            NH      OH             H   H473  4-tBu-Ph       NH          Ph             NH      OH             H   H474  4-tBu-Ph       NH          Bn             NH      OH             H   H475  4-tBu-Ph       NH          Pe             NH      OH             H   H476  4-tBu-Ph       NH          C12            NMe     OH             H   H477  4-tBu-Ph       NH          C12            NEt     OH             H   H478  4-tBu-Ph       NH          C12            NPr     OH             H   H479  4-tBu-Ph       NH          (CH2)3      N       OH             H   H480  4-tBu-Ph       NH          (CH2)4      N       OH             H   H481  4-tBu-Ph       NH          (CH2)5      N       OH             H   H482  4-tBu-Ph       NH           C12           O       OH             H   H483  4-tBu-Ph       NH           Ph            O       OH             H   H484  4-tBu-Ph       NH           C12           S       OH             H   H485  4-tBu-Ph       NH           Ph            S       OH             H   H486  4-tBu-Ph       NMe          H             NH      OH             H   H487  4-tBu-Ph       NEt          H             NH      OH             H   H488  4-tBu-Ph       NPr          H             NH      OH             H   H489  4-tBu-Ph       O            H             NH      OH             H   H490  4-tBu-Ph       S            H             NH      OH             H   H491  4-sBu-Ph       NH           H             NH      H              H   H492  4-sBu-Ph       NH           H             NH      OH             H   H493  4-sBu-Ph       NH           H             NH      OA6            H   H494  4-sBu-Ph       NH           H             NH      OA8            H   H495  4-sBu-Ph       NH           H             NH      OA9            H   H496  4-sBu-Ph       NH           H    NH           OA10           H    H497  4-sBu-Ph       NH           H    NH           OA12           H    H498  4-sBu-Ph       NH           H    NH           OA14           H    H499  4-sBu-Ph       NH           H    NH           OA16           H    H500  4-sBu-Ph       NH           H    NH           OH             H    A6501  4-sBu-Ph       NH           H    NH           OH             H    A8502  4-sBu-Ph       NH           H    NH           OH             H    A9503  4-sBu-Ph       NH           H    NH           OH             H    A10504  4-sBu-Ph       NH           H    NH           OH             H    A12505  4-sBu-Ph       NH           H    NH           OH             H    A14506  4-sBu-Ph       NH           H    NH           OH             H    A16507  4-sBu-Ph       NH           H    NH           OH             A6   A6508  4-sBu-Ph       NH           H    NH           OH             A8   A8509  4-sBu-Ph       NH           H    NH           OH             A10  A10510  4-sBu-Ph       NH           H    NH           OA2            A2   A2511  4-sBu-Ph       NH           H    NH           OA3            A3   A3512  4-sBu-Ph       NH           H    NH           OA4            A4   A4513  4-sBu-Ph       NH           H    NH           OC6            H    H514  4-sBu-Ph       NH           H    NH           OC7            H    H515  4-sBu-Ph       NH           H    NH           OC8            H    H516  4-sBu-Ph       NH           H    NH           OC10           H    H517  4-sBu-Ph       NH           H    NH           OC11           H    H518  4-sBu-Ph       NH           H    NH           OC12           H    H519  4-sBu-Ph       NH           H    NH           OC14           H    H520  4-sBu-Ph       NH           H    NH           OC16           H    H521  4-sBu-Ph       NH           H    NH           C6CO3         H    H522  4-sBu-Ph       NH           H    NH           C7CO3         H    H523  4-sBu-Ph       NH           H    NH           C8CO3         H    H524  4-sBu-Ph       NH           H    NH           C9CO3         H    H525  4-sBu-Ph        NH         H               NH   C10CO3          H    H526  4-sBu-Ph        NH         H               NH   C12CO3          H    H527  4-sBu-Ph        NH         H               NH   C16CO3          H    H528  4-sBu-Ph        NH         C8              NH   OH               H    H529  4-sBu-Ph        NH         C9              NH   OH               H    H530  4-sBu-Ph        NH         C10             NH   OH               H    H531  4-sBu-Ph        NH         C12             NH   OH               H    H532  4-sBu-Ph        NH         C16             NH   OH               H    H533  4-sBu-Ph        NH         F1              NH   OH               H    H534  4-sBu-Ph        NH         F2              NH   OH               H    H535  4-sBu-Ph        NH         F3              NH   OH               H    H536  4-sBu-Ph        NH         F4              NH   OH               H    H537  4-sBu-Ph        NH         F5              NH   OH               H    H538  4-sBu-Ph        NH         F6              NH   OH               H    H539  4-sBu-Ph        NH         F7              NH   OH               H    H540  4-sBu-Ph        NH         F8              NH   OH               H    H541  4-sBu-Ph        NH         F9              NH   OH               H    H542  4-sBu-Ph        NH         F10             NH   OH               H    H543  4-sBu-Ph        NH         Ph              NH   OH               H    H544  4-sBu-Ph        NH         Bn              NH   OH               H    H545  4-sBu-Ph        NH         Pe              NH   OH               H    H546  4-sBu-Ph        NH         C12             NMe  OH               H    H547  4-sBu-Ph        NH         C12             NEt  OH               H    H548  4-sBu-Ph        NH         C12             NPr  OH               H    H549  4-sBu-Ph        NH         (CH2)3       N    OH               H    H550  4-sBu-Ph        NH         (CH2)4       N    OH               H    H551  4-sBu-Ph        NH         (CH2)5       N    OH               H    H552  4-sBu-Ph        NH         C12             O    OH               H    H553  4-sBu-Ph        NH         Ph              O    OH               H    H554  4-sBu-Ph       NH         C12          S          OH     H          H555  4-sBu-Ph       NH         Ph           S          OH     H          H556  4-sBu-Ph       NMe        H            NH         OH     H          H557  4-sBu-Ph       NEt        H            NH         OH     H          H558  4-sBu-Ph       NPr        H            NH         OH     H          H559  4-sBu-Ph       O          H            NH         OH     H          H560  4-sBu-Ph       S          H            NH         OH     H          H561  4-Pen-Ph       NH         H            NH         H      H          H562  4-Pen-Ph       NH         H            NH         OH     H          H563  4-Pen-Ph       NH         H            NH         OA6    H          H564  4-Pen-Ph       NH         H            NH         OA8    H          H565  4-Pen-Ph       NH         H            NH         OA9    H          H566  4-Pen-Ph       NH         H            NH         OA10   H          H567  4-Pen-Ph       NH         H            NH         OA12   H          H568  4-Pen-Ph       NH         H            NH         OA14   H          H569  4-Pen-Ph       NH         H            NH         OA16   H          H570  4-Pen-Ph       NH         H            NH         OH     H          A6571  4-Pen-Ph       NH         H            NH         OH     H          A8572  4-Pen-Ph       NH         H            NH         OH     H          A9573  4-Pen-Ph       NH         H            NH         OH     H          A10574  4-Pen-Ph       NH         H            NH         OH     H          A12575  4-Pen-Ph       NH         H            NH         OH     H          A14578  4-Pen-Ph       NH         H            NH         OH     H          A16577  4-Pen-Ph       NH         H            NH         OH     A6         A6578  4-Pen-Ph       NH         H            NH         OH     A8         A8579  4-Pen-Ph       NH         H            NH         OH     A10        A10580  4-Pen-Ph       NH         H            NH         OA2    A2         A2581  4-Pen-Ph       NH         H            NH         OA3    A3         A3582  4-Pen-Ph       NH         H            NH         OA4    A4         A4583  4-Pen-Ph        NH          H      NH          OC6            H    H584  4-Pen-Ph        NH          H      NH          OC7            H    H585  4-Pen-Ph        NH          H      NH          OC8            H    H586  4-Pen-Ph        NH          H      NH          OC10           H    H587  4-Pen-Ph        NH          H      NH          OC11           H    H588  4-Pen-Ph        NH          H      NH          OC12           H    H589  4-Pen-Ph        NH          H      NH          OC14           H    H590  4-Pen-Ph        NH          H      NH          OC16           H    H591  4-Pen-Ph        NH          H      NH          C6CO3         H    H592  4-Pen-Ph        NH          H      NH          C7CO3         H    H593  4-Pen-Ph        NH          H      NH          C8CO3         H    H594  4-Pen-Ph        NH          H      NH          C9CO3         H    H595  4-Pen-Ph        NH          H      NH          C10CO3        H    H596  4-Pen-Ph        NH          H      NH          C12CO3        H    H597  4-Pen-Ph        NH          H      NH          C16CO3        H    H598  4-Pen-Ph        NH          C8     NH          OH             H    H599  4-Pen-Ph        NH          C9     NH          OH             H    H600  4-Pen-Ph        NH          C10    NH          OH             H    H601  4-Pen-Ph        NH          C12    NH          OH             H    H602  4-Pen-Ph        NH          C16    NH          OH             H    H603  4-Pen-Ph        NH          F1     NH          OH             H    H604  4-Pen-Ph        NH          F2     NH          OH             H    H605  4-Pen-Ph        NH          F3     NH          OH             H    H606  4-Pen-Ph        NH          F4     NH          OH             H    H607  4-Pen-Ph        NH          F5     NH          OH             H    H608  4-Pen-Ph        NH          F6     NH          OH             H    H609  4-Pen-Ph        NH          F7     NH          OH             H    H610  4-Pen-Ph        NH          F8     NH          OH             H    H611  4-Pen-Ph        NH          F9     NH          OH             H    H612  4-Pen-Ph       NH         F10          NH         OH            H    H613  4-Pen-Ph       NH         Ph           NH         OH            H    H614  4-Pen-Ph       NH         Bn           NH         OH            H    H615  4-Pen-Ph       NH         Pe           NH         OH            H    H616  4-Pen-Ph       NH         C12          NMe        OH            H    H617  4-Pen-Ph       NH         C12          NEt        OH            H    H618  4-Pen-Ph       NH         C12          NPr        OH            H    H619  4-Pen-Ph       NH         (CH2)3    N          OH            H    H620  4-Pen-Ph       NH         (CH2)4    N          OH            H    H621  4-Pen-Ph       NH         (CH2)5    N          OH            H    H622  4-Pen-Ph       NH         C12          O          OH            H    H623  4-Pen-Ph       NH         Ph           O          OH            H    H624  4-Pen-Ph       NH         C12          S          OH            H    H625  4-Pen-Ph       NH         Ph           S          OH            H    H626  4-Pen-Ph       NMe        H            NH         OH            H    H627  4-Pen-Ph       NEt        H            NH         OH            H    H628  4-Pen-Ph       NPr        H            NH         OH            H    H629  4-Pen-Ph       O          H            NH         OH            H    H630  4-Pen-Ph       S          H            NH         OH            H    H631  4-Hex-Ph       NH         H            NH         H             H    H632  4-Hex-Ph       NH         H            NH         OH            H    H633  4-Hex-Ph       NH         H            NH         OA6           H    H634  4-Hex-Ph       NH         H            NH         OA8           H    H635  4-Hex-Ph       NH         H            NH         OA9           H    H636  4-Hex-Ph       NH         H            NH         OA10          H    H637  4-Hex-Ph       NH         H            NH         OA12          H    H638  4-Hex-Ph       NH         H            NH         OA14          H    H639  4-Hex-Ph       NH         H            NH         OA16          H    H640  4-Hex-Ph       NH         H            NH         OH            H    A6641  4-Hex-Ph       NH         H           NH         OH           H    A8642  4-Hex-Ph       NH         H           NH         OH           H    A9643  4-Hex-Ph       NH         H           NH         OH           H    A10644  4-Hex-Ph       NH         H           NH         OH           H    A12645  4-Hex-Ph       NH         H           NH         OH           H    A14646  4-Hex-Ph       NH         H           NH         OH           H    A16647  4-Hex-Ph       NH         H           NH         OH           A6   A6648  4-Hex-Ph       NH         H           NH         OH           A8   A8649  4-Hex-Ph       NH         H           NH         OH           A10  A10650  4-Hex-Ph       NH         H           NH         OA2          A2   A2651  4-Hex-Ph       NH         H           NH         OA3          A3   A3652  4-Hex-Ph       NH         H           NH         OA4          A4   A4653  4-Hex-Ph       NH         H           NH         OC6          H    H654  4-Hex-Ph       NH         H           NH         OC7          H    H655  4-Hex-Ph       NH         H           NH         OC8          H    H656  4-Hex-Ph       NH         H           NH         OC10         H    H657  4-Hex-Ph       NH         H           NH         OC11         H    H658  4-Hex-Ph       NH         H           NH         OC12         H    H659  4-Hex-Ph       NH         H           NH         OC14         H    H660  4-Hex-Ph       NH         H           NH         OC16         H    H661   4-Hex-Ph      NH         H           NH         C6CO3       H    H662  4-Hex-Ph       NH         H           NH         C7CO3       H    H663  4-Hex-Ph       NH         H           NH         C8CO3       H    H664  4-Hex-Ph       NH         H           NH         C9CO3       H    H665  4-Hex-Ph       NH         H           NH         C10CO3      H    H666  4-Hex-Ph       NH         H           NH         C12CO3      H    H667  4-Hex-Ph       NH         H           NH         C16CO3      H    H668  4-Hex-Ph       NH         C8          NH         OH           H    H669  4-Hex-Ph       NH         C9          NH         OH           H    H670  4-Hex-Ph        NH         C1O          NH         OH            H    H671  4-Hex-Ph        NH         C12          NH         OH            H    H672  4-Hex-Ph        NH         C16          NH         OH            H    H673  4-Hex-Ph        NH         F1           NH         OH            H    H674  4-Hex-Ph        NH         F2           NH         OH            H    H675  4-Hex-Ph        NH         F3           NH         OH            H    H676  4-Hex-Ph        NH         F4           NH         OH            H    H677  4-Hex-Ph        NH         F5           NH         OH            H    H678  4-Hex-Ph        NH         F6           NH         OH            H    H679  4-Hex-Ph        NH         F7           NH         OH            H    H680  4-Hex-Ph        NH         F8           NH         OH            H    H681  4-Hex-Ph        NH         F9           NH         OH            H    H682  4-Hex-Ph        NH         F10          NH         OH            H    H683  4-Hex-Ph        NH         Ph           NH         OH            H    H684  4-Hex-Ph        NH         Bn           NH         OH            H    H685  4-Hex-Ph        NH         Pe           NH         OH            H    H686  4-Hex-Ph        NH         C12          NMe        OH            H    H687  4-Hex-Ph        NH         C12          NEt        OH            H    H688  4-Hex-Ph        NH         C12          NPr        OH            H    H689  4-Hex-Ph        NH         (CH2)3    N          OH            H    H690  4-Hex-Ph        NH         (CH2)4    N          OH            H    H691  4-Hex-Ph        NH         (CH2)5    N          OH            H    H692  4-Hex-Ph        NH         C12          O          OH            H    H693  4-Hex-Ph        NH         Ph           O          OH            H    H694  4-Hex-Ph        NH         C12          S          OH            H    H695  4-Hex-Ph        NH         Ph           S          OH            H    H696  4-Hex-Ph        NMe        H            NH         OH            H    H697  4-Hex-Ph        NEt        H            NH         OH            H    H698  4-Hex-Ph        NPr        H            NH         OH            H    H699  4-Hex-Ph       O         H     NH         OH             H         H700  4-Hex-Ph       S         H     NH         OH             H         H701  4-Hep-Ph       NH        H     NH         H              H         H702  4-Hep-Ph       NH        H     NH         OH             H         H703  4-Hep-Ph       NH        H     NH         OA6            H         H704  4-Hep-Ph       NH        H     NH         OA8            H         H705  4-Hep-Ph       NH        H     NH         OA9            H         H706  4-Hep-Ph       NH        H     NH         OA10           H         H707  4-Hep-Ph       NH        H     NH         OA12           H         H708  4-Hep-Ph       NH        H     NH         OA14           H         H709  4-Hep-Ph       NH        H     NH         OA16           H         H710  4-Hep-Ph       NH        H     NH         OH             H         A6711  4-Hep-Ph       NH        H     NH         OH             H         A8712  4-Hep-Ph       NH        H     NH         OH             H         A9713  4-Hep-Ph       NH        H     NH         OH             H         A10714  4-Hep-Ph       NH        H     NH         OH             H         A12715  4-Hep-Ph       NH        H     NH         OH             H         A14716  4-Hep-Ph       NH        H     NH         OH             H         A16717  4-Hep-Ph       NH        H     NH         OH             A6        A6718  4-Hep-Ph       NH        H     NH         OH             A8        A8719  4-Hep-Ph       NH        H     NH         OH             A10       A10720  4-Hep-Ph       NH        H     NH         OA2            A2        A2721  4-Hep-Ph       NH        H     NH         OA3            A3        A3722  4-Hep-Ph       NH        H     NH         OA4            A4        A4723  4-Hep-Ph       NH        H     NH         OC6            H         H724  4-Hep-Ph       NH        H     NH         OC7            H         H725  4-Hep-Ph       NH        H     NH         OC8            H         H726  4-Hep-Ph       NH        H     NH         OC10           H         H727  4-Hep-Ph       NH        H     NH         OC11           H         H728  4-Hep-Ph      NH       H             NH           OC12            H   H729  4-Hep-Ph      NH       H             NH           OC14            H   H730  4-Hep-Ph      NH       H             NH           OC16            H   H731  4-Hep-Ph      NH       H             NH           C6CO3          H   H732  4-Hep-Ph      NH       H             NH           C7CO3          H   H733  4-Hep-Ph      NH       H             NH           C8CO3          H   H734  4-Hep-Ph      NH       H             NH           C9CO3          H   H735  4-Hep-Ph      NH       H             NH           C10CO3         H   H736  4-Hep-Ph      NH       H             NH           C12CO3         H   H737  4-Hep-Ph      NH       H             NH           C16CO3         H   H738  4-Hep-Ph      NH       C8            NH           OH              H   H739  4-Hep-Ph      NH       C9            NH           OH              H   H740  4-Hep-Ph      NH       C10           NH           OH              H   H741  4-Hep-Ph      NH       C12           NH           OH              H   H742  4-Hep-Ph      NH       C16           NH           OH              H   H743  4-Hep-Ph      NH       F1            NH           OH              H   H744  4-Hep-Ph      NH       F2            NH           OH              H   H745  4-Hep-Ph      NH       F3            NH           OH              H   H746  4-Hep-Ph      NH       F4            NH           OH              H   H747  4-Hep-Ph      NH       F5            NH           OH              H   H748  4-Hep-Ph      NH       F6            NH           OH              H   H749  4-Hep-Ph      NH       F7            NH           OH              H   H750  4-Hep-Ph      NH       F8            NH           OH              H   H751  4-Hep-Ph      NH       F9            NH           OH              H   H752  4-Hep-Ph      NH       F10           NH           OH              H   H753  4-Hep-Ph      NH       Ph            NH           OH              H   H754  4-Hep-Ph      NH       Bn            NH           OH              H   H755  4-Hep-Ph      NH       Pe            NH           OH              H   H756  4-Hep-Ph      NH       C12           NMe          OH              H   H757  4-Hep-Ph       NH            C12             NEt  OH              H   H758  4-Hep-Ph       NH            C12             NPr  OH              H   H759  4-Hep-Ph       NH            (CH2)3       N    OH              H   H760  4-Hep-Ph       NH            (CH2)4       N    OH              H   H761  4-Hep-Ph       NH            (CH2)5       N    OH              H   H762  4-Hep-Ph       NH            C12             O    OH              H   H763  4-Hep-Ph       NH            Ph              O    OH              H   H764  4-Hep-Ph       NH            C12             S    OH              H   H765  4-Hep-Ph       NH            Ph              S    OH              H   H766  4-Hep-Ph       NMe           H               NH   OH              H   H767  4-Hep-Ph       NEt           H               NH   OH              H   H768  4-Hep-Ph       NPr           H               NH   OH              H   H769  4-Hep-Ph       O             H               NH   OH              H   H770  4-Hep-Ph       S             H               NH   OH              H   H771  4-Oct-Ph       NH            H               NH   H               H   H772  4-Oct-Ph       NH            H               NH   OH              H   H773  4-Oct-Ph       NH            H               NH   OA6             H   H774  4-Oct-Ph       NH            H               NH   OA8             H   H775  4-Oct-Ph       NH            H               NH   OA9             H   H776  4-Oct-Ph       NH            H               NH   OA10            H   H777  4-Oct-Ph       NH            H               NH   OA12            H   H778  4-Oct-Ph       NH            H               NH   OA14            H   H779  4-Oct-Ph       NH            H               NH   OA16            H   H780  4-Oct-Ph       NH            H               NH   OH              H   A6781  4-Oct-Ph       NH            H               NH   OH              H   A8782  4-Oct-Ph       NH            H               NH   OH              H   A9783  4-Oct-Ph       NH            H               NH   OH              H   A10784  4-Oct-Ph       NH            H               NH   OH              H   A12785  4-Oct-Ph       NH            H               NH   OH              H   A14786     4-Oct-Ph                 NH      H             NH      OH           H        A16787     4-Oct-Ph                 NH      H             NH      OH           A6       A6788     4-Oct-Ph                 NH      H             NH      OH           A8       A8789     4-Oct-Ph                 NH      H             NH      OH           A10      A10790     4-Oct-Ph                 NH      H             NH      OA2          A2       A2791     4-Oct-Ph                 NH      H             NH      OA3          A3       A3792     4-Oct-Ph                 NH      H             NH      OA4          A4       A4793     4-Oct-Ph                 NH      H             NH      OC6          H        H794     4-Oct-Ph                 NH      H             NH      OC7          H        H795     4-Oct-Ph                 NH      H             NH      OC8          H        H796     4-Oct-Ph                 NH      H             NH      OC10         H        H797     4-Oct-Ph                 NH      H             NH      OC11         H        H798     4-Oct-Ph                 NH      H             NH      OC12         H        H799     4-Oct-Ph                 NH      H             NH      OC14         H        H800     4-Oct-Ph                 NH      H             NH      OC16         H        H801     4-Oct-Ph                 NH      H             NH      C6CO3       H        H802     4-Oct-Ph                 NH      H             NH      C7CO3       H        H803     4-Oct-Ph                 NH      H             NH      C8CO3       H        H804     4-Oct-Ph                 NH      H             NH      C9CO3       H        H805     4-Oct-Ph                 NH      H             NH      C10CO3      H        H806     4-Oct-Ph                 NH      H             NH      C12CO3      H        H807     4-Oct-Ph                 NH      H             NH      C16CO3      H        H808     4-Oct-Ph                 NH      C8            NH      OH           H        H809     4-Oct-Ph                 NH      C9            NH      OH           H        H810     4-Oct-Ph                 NH      C10           NH      OH           H        H811     4-Oct-Ph                 NH      C12           NH      OH           H        H812     4-Oct-Ph                 NH      C16           NH      OH           H        H813     4-Oct-Ph                 NH      F1            NH      OH           H        H814     4-Oct-Ph                 NH      F2            NH      OH           H        H815  4-Oct-Ph       NH       F3            NH          OH              H   H816  4-Oct-Ph       NH       F4            NH          OH              H   H817  4-Oct-Ph       NH       F5            NH          OH              H   H818  4-Oct-Ph       NH       F6            NH          OH              H   H819  4-Oct-Ph       NH       F7            NH          OH              H   H820  4-Oct-Ph       NH       F8            NH          OH              H   H821  4-Oct-Ph       NH       F9            NH          OH              H   H822  4-Oct-Ph       NH       F10           NH          OH              H   H823  4-Oct-Ph       NH       Ph            NH          OH              H   H824  4-Oct-Ph       NH       Bn            NH          OH              H   H825  4-Oct-Ph       NH       Pe            NH          OH              H   H826  4-Oct-Ph       NH       C12           NMe         OH              H   H827  4-Oct-Ph       NH       C12           NEt         OH              H   H828  4-Oct-Ph       NH       C12           NPr         OH              H   H829  4-Oct-Ph       NH       (CH2)3     N           OH              H   H830  4-Oct-Ph       NH       (CH2)4     N           OH              H   H831  4-Oct-Ph       NH       (CH2)5     N           OH              H   H832  4-Oct-Ph       NH       C12           O           OH              H   H833  4-Oct-Ph       NH       Ph            O           OH              H   H834  4-Oct-Ph       NH       C12           S           OH              H   H835  4-Oct-Ph       NH       Ph            S           OH              H   H836  4-Oct-Ph       NMe      H             NH          OH              H   H837  4-Oct-Ph       NEt      H             NH          OH              H   H838  4-Oct-Ph       NPr      H             NH          OH              H   H839  4-Oct-Ph       O        H             NH          OH              H   H840  4-Oct-Ph       S        H             NH          OH              H   H841  4-Dec-Ph       NH       H             NH          H               H   H842  4-Dec-Ph       NH       H             NH          OH              H   H843  4-Dec-Ph       NH       H             NH          OA6             H   H844  4-Dec-Ph      NH         H           NH         OA8           H          H845  4-Dec-Ph      NH         H           NH         OA9           H          H846  4-Dec-Ph      NH         H           NH         OA10          H          H847  4-Dec-Ph      NH         H           NH         OA12          H          H848  4-Dec-Ph      NH         H           NH         OA14          H          H849  4-Dec-Ph      NH         H           NH         OA16          H          H850  4-Dec-Ph      NH         H           NH         OH            H          A6851  4-Dec-Ph      NH         H           NH         OH            H          A8852  4-Dec-Ph      NH         H           NH         OH            H          A9853  4-Dec-Ph      NH         H           NH         OH            H          A10854  4-Dec-Ph      NH         H           NH         OH            H          A12855  4-Dec-Ph      NH         H           NH         OH            H          A14856  4-Dec-Ph      NH         H           NH         OH            H          A16857  4-Dec-Ph      NH         H           NH         OH            A6         A6858  4-Dec-Ph      NH         H           NH         OH            A8         A8859  4-Dec-Ph      NH         H           NH         OH            A10        A10860  4-Dec-Ph      NH         H           NH         OA2           A2         A2861  4-Dec-Ph      NH         H           NH         OA3           A3         A3862  4-Dec-Ph      NH         H           NH         OA4           A4         A4863  4-Dec-Ph      NH         H           NH         OC6           H          H864  4-Dec-Ph      NH         H           NH         OC7           H          H865  4-Dec-Ph      NH         H           NH         OC8           H          H866  4-Dec-Ph      NH         H           NH         OC10          H          H867  4-Dec-Ph      NH         H           NH         OC11          H          H868  4-Dec-Ph      NH         H           NH         OC12          H          H869  4-Dec-Ph      NH         H           NH         OC14          H          H870  4-Dec-Ph      NH         H           NH         OC16          H          H871  4-Dec-Ph      NH         H           NH         C6CO3        H          H872  4-Dec-Ph      NH         H           NH         C7CO3        H          H873  4-Dec-Ph       NH   H               NH            C8CO3          H    H874  4-Dec-Ph       NH   H               NH            C9CO3          H    H875  4-Dec-Ph       NH   H               NH            C10CO3         H    H876  4-Dec-Ph       NH   H               NH            C12CO3         H    H877  4-Dec-Ph       NH   H               NH            C16CO3         H    H878  4-Dec-Ph       NH   C8              NH            OH              H    H879  4-Dec-Ph       NH   C9              NH            OH              H    H880  4-Dec-Ph       NH   C10             NH            OH              H    H881  4-Dec-Ph       NH   C12             NH            OH              H    H882  4-Dec-Ph       NH   C16             NH            OH              H    H883  4-Dec-Ph       NH   F1              NH            OH              H    H884  4-Dec-Ph       NH   F2              NH            OH              H    H885  4-Dec-Ph       NH   F3              NH            OH              H    H886  4-Dec-Ph       NH   F4              NH            OH              H    H887  4-Dec-Ph       NH   F5              NH            OH              H    H888  4-Dec-Ph       NH   F6              NH            OH              H    H889  4-Dec-Ph       NH   F7              NH            OH              H    H890  4-Dec-Ph       NH   F8              NH            OH              H    H891  4-Dec-Ph       NH   F9              NH            OH              H    H892  4-Dec-Ph       NH   F10             NH            OH              H    H893  4-Dec-Ph       NH   Ph              NH            OH              H    H894  4-Dec-Ph       NH   Bn              NH            OH              H    H895  4-Dec-Ph       NH   Pe              NH            OH              H    H896  4-Dec-Ph       NH   C12             NMe           OH              H    H897  4-Dec-Ph       NH   C12             NEt           OH              H    H898  4-Dec-Ph       NH   C12             NPr           OH              H    H899  4-Dec-Ph       NH   (CH2)3       N             OH              H    H900  4-Dec-Ph       NH   (CH2)4       N             OH              H    H901  4-Dec-Ph       NH   (CH2)5       N             OH              H    H902  4-Dec-Ph       NH            C12            O    OH              H    H903  4-Dec-Ph       NH            Ph             O    OH              H    H904  4-Dec-Ph       NH            C12            S    OH              H    H905  4-Dec-Ph       NH            Ph             S    OH              H    H906  4-Dec-Ph       NMe           H              NH   OH              H    H907  4-Dec-Ph       NEt           H              NH   OH              H    H908  4-Dec-Ph       NPr           H              NH   OH              H    H909  4-Dec-Ph       O             H              NH   OH              H    H910  4-Dec-Ph       S             H              NH   OH              H    H911  3-Me-Ph        NH            H              NH   H               H    H912  3-Me-Ph        NH            H              NH   OH              H    H913  3-Me-Ph        NH            H              NH   OA6             H    H914  3-Me-Ph        NH            H              NH   OA8             H    H915  3-Me-Ph        NH            H              NH   OA9             H    H916  3-Me-Ph        NH            H              NH   OA10            H    H917  3-Me-Ph        NH            H              NH   OA12            H    H918  3-Me-Ph        NH            H              NH   OA14            H    H919  3-Me-Ph        NH            H              NH   OA16            H    H920  3-Me-Ph        NH            H              NH   OH              H    A6921  3-Me-Ph        NH            H              NH   OH              H    A8922  3-Me-Ph        NH            H              NH   OH              H    A9923  3-Me-Ph        NH            H              NH   OH              H    A10924  3-Me-Ph        NH            H              NH   OH              H    A12925  3-Me-Ph        NH            H              NH   OH              H    A14926  3-Me-Ph        NH            H              N    OH              H    A16927  3-Me-Ph        NH            H              NH   OH              A6   A6928  3-Me-Ph        NH            H              NH   OH              A8   A8929  3-Me-Ph        NH            H              NH   OH              A10  A10930  3-Me-Ph        NH            H              NH   OA2             A2   A2931  3-Me-Ph       NH           H     NH          OA3            A3  A3932  3-Me-Ph       NH           H     NH          OA4            A4  A4933  3-Me-Ph       NH           H     NH          OC6            H   H934  3-Me-Ph       NH           H     NH          OC7            H   H935  3-Me-Ph       NH           H     NH          OC8            H   H936  3-Me-Ph       NH           H     NH          OC10           H   H937  3-Me-Ph       NH           H     NH          OC11           H   H938  3-Me-Ph       NH           H     NH          OC12           H   H939  3-Me-Ph       NH           H     NH          OC14           H   H940  3-Me-Ph       NH           H     NH          OC16           H   H941  3-Me-Ph       NH           H     NH          C6CO3         H   H942  3-Me-Ph       NH           H     NH          C7CO3         H   H943  3-Me-Ph       NH           H     NH          C8CO3         H   H944  3-Me-Ph       NH           H     NH          C9CO3         H   H945  3-Me-Ph       NH           H     NH          C10CO3        H   H946  3-Me-Ph       NH           H     NH          C12CO3        H   H947  3-Me-Ph       NH           H     NH          C16CO3        H   H948  3-Me-Ph       NH           C8    NH          OH             H   H949  3-Me-Ph       NH           C9    NH          OH             H   H950  3-Me-Ph       NH           C10   NH          OH             H   H951  3-Me-Ph       NH           C12   NH          OH             H   H952  3-Me-Ph       NH           C16   NH          OH             H   H953  3-Me-Ph       NH           F1    NH          OH             H   H954  3-Me-Ph       NH           F2    NH          OH             H   H955  3-Me-Ph       NH           F3    NH          OH             H   H956  3-Me-Ph       NH           F4    NH          OH             H   H957  3-Me-Ph       NH           F5    NH          OH             H   H958  3-Me-Ph       NH           F6    NH          OH             H   H959  3-Me-Ph       NH           F7    NH          OH             H   H960  3-Me-Ph        NH          F8            NH         OH            H    H961  3-Me-Ph        NH          F9            NH         OH            H    H962  3-Me-Ph        NH          F10           NH         OH            H    H963  3-Me-Ph        NH          Ph            NH         OH            H    H964  3-Me-Ph        NH          Bn            NH         OH            H    H965  3-Me-Ph        NH          Pe            NH         OH            H    H966  3-Me-Ph        NH          C12           NMe        OH            H    H967  3-Me-Ph        NH          C12           NEt        OH            H    H968  3-Me-Ph        NH          C12           NPr        OH            H    H969  3-Me-Ph        NH          (CH2)3     N          OH            H    H970  3-Me-Ph        NH          (CH2)4     N          OH            H    H971  3-Me-Ph        NH          (CH2)5     N          OH            H    H972  3-Me-Ph        NH          C12           O          OH            H    H973  3-Me-Ph        NH          Ph            O          OH            H    H974  3-Me-Ph        NH          C12           S          OH            H    H975  3-Me-Ph        NH          Ph            S          OH            H    H976  3-Me-Ph        NMe         H             NH         OH            H    H977  3-Me-Ph        NEt         H             NH         OH            H    H978  3-Me-Ph        NPr         H             NH         OH            H    H979  3-Me-Ph        O           H             NH         OH            H    H980  3-Me-Ph        S           H             NH         OH            H    H981  3-Et-Ph        NH          H             NH         H             H    H982  3-Et-Ph        NH          H             NH         OH            H    H983  3-Et-Ph        NH          H             NH         OA6           H    H984  3-Et-Ph        NH          H             NH         OA8           H    H985  3-Et-Ph        NH          H             NH         OA9           H    H986  3-Et-Ph        NH          H             NH         OA10          H    H987  3-Et-Ph        NH          H             NH         OA12          H    H988  3-Et-Ph        NH          H             NH         OA14          H    H989     3-Et-Ph                   NH      H            NH      OA16         H        H990     3-Et-Ph                   NH      H            NH      OH           H        A6991     3-Et-Ph                   NH      H            NH      OH           H        A8992     3-Et-Ph                   NH      H            NH      OH           H        A9993     3-Et-Ph                   NH      H            NH      OH           H        A10994     3-Et-Ph                   NH      H            NH      OH           H        A12995     3-Et-Ph                   NH      H            NH      OH           H        A14996     3-Et-Ph                   NH      H            NH      OH           H        A16997     3-Et-Ph                   NH      H            NH      OH           A6       A6998     3-Et-Ph                   NH      H            NH      OH           A8       A8999     3-Et-Ph                   NH      H            NH      OH           A10      A101000    3-Et-Ph                   NH      H            NH      OA2          A2       A21001    3-Et-Ph                   NH      H            NH      OA3          A3       A31002    3-Et-Ph                   NH      H            NH      OA4          A4       A41003    3-Et-Ph                   NH      H            NH      OC6          H        H1004    3-Et-Ph                   NH      H            NH      OC7          H        H1005    3-Et-Ph                   NH      H            NH      OC8          H        H1006    3-Et-Ph                   NH      H            NH      OC10         H        H1007    3-Et-Ph                   NH      H            NH      OC11         H        H1008    3-Et-Ph                   NH      H            NH      OC12         H        H1009    3-Et-Ph                   NH      H            NH      OC14         H        H1010    3-Et-Ph                   NH      H            NH      OC16         H        H1011    3-Et-Ph                   NH      H            NH      C6CO3       H        H1012    3-Et-Ph                   NH      H            NH      C7CO3       H        H1013    3-Et-Ph                   NH      H            NH      C8CO3       H        H1014    3-Et-Ph                   NH      H            NH      C9CO3       H        H1015    3-Et-Ph                   NH      H            NH      C10CO3      H        H1016    3-Et-Ph                   NH      H            NH      C12CO3      H        H1017    3-Et-Ph                   NH      H            NH      C16CO3      H        H1018   3-Et-Ph       NH        C8              NH        OH              H   H1019   3-Et-Ph       NH        C9              NH        OH              H   H1020   3-Et-Ph       NH        C10             NH        OH              H   H1021   3-Et-Ph       NH        C12             NH        OH              H   H1022   3-Et-Ph       NH        C16             NH        OH              H   H1023   3-Et-Ph       NH        F1              NH        OH              H   H1024   3-Et-Ph       NH        F2              NH        OH              H   H1025   3-Et-Ph       NH        F3              NH        OH              H   H1026   3-Et-Ph       NH        F4              NH        OH              H   H1027   3-Et-Ph       NH        F5              NH        OH              H   H1028   3-Et-Ph       NH        F6              NH        OH              H   H1029   3-Et-Ph       NH        F7              NH        OH              H   H1030   3-Et-Ph       NH        F8              NH        OH              H   H1031   3-Et-Ph       NH        F9              NH        OH              H   H1032   3-Et-Ph       NH        F10             NH        OH              H   H1033   3-Et-Ph       NH        Ph              NH        OH              H   H1034   3-Et-Ph       NH        Bn              NH        OH              H   H1035   3-Et-Ph       NH        Pe              NH        OH              H   H1036   3-Et-Ph       NH        C12             NMe       OH              H   H1037   3-Et-Ph       NH        C12             NEt       OH              H   H1038   3-Et-Ph       NH        C12             NPr       OH              H   H1039   3-Et-Ph       NH        (CH2)3       N         OH              H   H1040   3-Et-Ph       NH        (CH2)4       N         OH              H   H1041   3-Et-Ph       NH        (CH2)5       N         OH              H   H1042   3-Et-Ph       NH        C12             O         OH              H   H1043   3-Et-Ph       NH        Ph              O         OH              H   H1044   3-Et-Ph       NH        C12             S         OH              H   H1045   3-Et-Ph       NH        Ph              S         OH              H   H1046   3-Et-Ph       NMe       H               NH        OH              H   H1047   3-Et-Ph         NEt          H             NH           OH             H    H1048   3-Et-Ph         NPr          H             NH           OH             H    H1049   3-Et-Ph         O            H             NH           OH             H    H1050   3-Et-Ph         S            H             NH           OH             H    H1051   3-iPr-Ph        NH           H             NH           H              H    H1052   3-iPr-Ph        NH           H             NH           OH             H    H1053   3-iPr-Ph        NH           H             NH           OA6            H    H1054   3-iPr-Ph        NH           H             NH           OA8            H    H1055   3-iPr-Ph        NH           H             NH           OA9            H    H1056   3-iPr-Ph        NH           H             NH           OA10           H    H1057   3-iPr-Ph        NH           H             NH           OA12           H    H1058   3-iPr-Ph        NH           H             NH           OA14           H    H1059   3-iPr-Ph        NH           H             NH           OA16           H    H1060   3-iPr-Ph        NH           H             NH           OH             H    A61061   3-iPr-Ph        NH           H             NH           OH             H    A81062   3-iPr-Ph        NH           H             NH           OH             H    A91063   3-iPr-Ph        NH           H             NH           OH             H    A101064   3-iPr-Ph        NH           H             NH           OH             H    A121065   3-iPr-Ph        NH           H             NH           OH             H    A141066   3-iPr-Ph        H            H             NH           OH             H    A161067   3-iPr-Ph        NH           H             NH           OH             A6   A61068   3-iPr-Ph        NH           H             NH           OH             A8   A81069   3-iPr-Ph        NH           H             NH           OH             A10  A101070   3-iPr-Ph        NH           H             NH           OA2            A2   A21071   3-iPr-Ph        NH           H             NH           OA3            A3   A31072   3-iPr-Ph        NH           H             NH           OA4            A4   A41073   3-iPr-Ph        NH           H             NH           OC6            H    H1074   3-iPr-Ph        NH           H             NH           OC7            H    H1075   3-iPr-Ph        NH           H             NH           OC8            H    H1076   3-iPr-Ph      NH           H             NH           OC10            H   H1077   3-iPr-Ph      NH           H             NH           OC11            H   H1078   3-iPr-Ph      NH           H             NH           OC12            H   H1079   3-iPr-Ph      NH           H             NH           OC14            H   H1080   3-iPr-Ph      NH           H             NH           OC16            H   H1081   3-iPr-Ph      NH           H             NH           C6CO3          H   H1082   3-iPr-Ph      NH           H             NH           C7CO3          H   H1083   3-iPr-Ph      NH           H             NH           C8CO3          H   H1084   3-iPr-Ph      NH           H             NH           C9CO3          H   H1085   3-iPr-Ph      NH           H             NH           C10CO3         H   H1086   3-iPr-Ph      NH           H             NH           C12CO3         H   H1087   3-iPr-Ph      NH           H             NH           C16CO3         H   H1088   3-iPr-Ph      NH           C8            NH           OH              H   H1089   3-iPr-Ph      NH           C9            NH           OH              H   H1090   3-iPr-Ph      NH           C10           NH           OH              H   H1091   3-iPr-Ph      NH           C12           NH           OH              H   H1092   3-iPr-Ph      NH           C16           NH           OH              H   H1093   3-iPr-Ph      NH           F1            NH           OH              H   H1094   3-iPr-Ph      NH           F2            NH           OH              H   H1095   3-iPr-Ph      NH           F3            NH           OH              H   H1096   3-iPr-Ph      NH           F4            NH           OH              H   H1097   3-iPr-Ph      NH           F5            NH           OH              H   H1098   3-iPr-Ph      NH           F6            NH           OH              H   H1099   3-iPr-Ph      NH           F7            NH           OH              H   H1100   3-iPr-Ph      NH           F8            NH           OH              H   H1101   3-iPr-Ph      NH           F9            NH           OH              H   H1102   3-iPr-Ph      NH           F10           NH           OH              H   H1103   3-iPr-Ph      NH           Ph            NH           OH              H   H1104   3-iPr-Ph      NH           Bn            NH           OH              H   H1105   3-iPr-Ph                  NH      Pe           NH       OH           H        H1106   3-iPr-Ph                  NH      C12          NMe      OH           H        H1107   3-iPr-Ph                  NH      C12          NEt      OH           H        H1108   3-iPr-Ph                  NH      C12          NPr      OH           H        H1109   3-iPr-Ph                  NH      (CH2)3    N        OH           H        H1110   3-iPr-Ph                  NH      (CH2)4    N        OH           H        H1111   3-iPr-Ph                  NH      (CH2)5    N        OH           H        H1112   3-iPr-Ph                  NH      C12          O        OH           H        H1113   3-iPr-Ph                  NH      Ph           O        OH           H        H1114   3-iPr-Ph                  NH      C12          S        OH           H        H1115   3-iPr-Ph                  NH      Ph           S        OH           H        H1116   3-iPr-Ph                  NMe     H            NH       OH           H        H1117   3-iPr-Ph                  NEt     H            NH       OH           H        H1118   3-iPr-Ph                  NPr     H            NH       OH           H        H1119   3-iPr-Ph                  O       H            NH       OH           H        H1120   3-iPr-Ph                  S       H            NH       OH           H        H1121   2-Et-Ph                   NH      H            NH       H            H        H1122   2-Et-Ph                   NH      H            NH       OH           H        H1123   2-Et-Ph                   NH      H            NH       OA6          H        H1124   2-Et-Ph                   NH      H            NH       OA8          H        H1125   2-Et-Ph                   NH      H            NH       OA9          H        H1126   2-Et-Ph                   NH      H            NH       OA10         H        H1127   2-Et-Ph                   NH      H            NH       OA12         H        H1128   2-Et-Ph                   NH      H            NH       OA14         H        H1129   2-Et-Ph                   NH      H            NH       OA16         H        H1130   2-Et-Ph                   NH      H            NH       OH           H        A61131   2-Et-Ph                   NH      H            NH       OH           H        A81132   2-Et-Ph                   NH      H            NH       OH           H        A91133   2-Et-Ph                   NH      H            NH       OH           H        A101134   2-Et-Ph        NH          H             NH          OH             H   A121135   2-Et-Ph        NH          H             NH          OH             H   A141136   2-Et-Ph        NH          H             NH          OH             H   A161137   2-Et-Ph        NH          H             NH          OH             A6  A61138   2-Et-Ph        NH          H             NH          OH             A8  A81139   2-Et-Ph        NH          H             NH          OH             A10 A101140   2-Et-Ph        NH          H             NH          OA2            A2  A21141   2-Et-Ph        NH          H             NH          OA3            A3  A31142   2-Et-Ph        NH          H             NH          OA4            A4  A41143   2-Et-Ph        NH          H             NH          OC6            H   H1144   2-Et-Ph        NH          H             NH          OC7            H   H1145   2-Et-Ph        NH          H             NH          OC8            H   H1146   2-Et-Ph        NH          H             NH          OC10           H   H1147   2-Et-Ph        NH          H             NH          OC11           H   H1148   2-Et-Ph        NH          H             NH          OC12           H   H1149   2-Et-Ph        NH          H             NH          OC14           H   H1150   2-Et-Ph        NH          H             NH          OC16           H   H1151   2-Et-Ph        NH          H             NH          C6CO3         H   H1152   2-Et-Ph        NH          H             NH          C7CO3         H   H1153   2-Et-Ph        NH          H             NH          C8CO3         H   H1154   2-Et-Ph        NH          H             NH          C9CO3         H   H1155   2-Et-Ph        NH          H             NH          C10CO3        H   H1156   2-Et-Ph        NH          H             NH          C12CO3        H   H1157   2-Et-Ph        NH          H             NH          C16CO3        H   H1158   2-Et-Ph        NH          C8            NH          OH             H   H1159   2-Et-Ph        NH          C9            NH          OH             H   H1160   2-Et-Ph        NH          C10           NH          OH             H   H1161   2-Et-Ph        NH          C12           NH          OH             H   H1162   2-Et-Ph        NH          C16           NH          OH             H   H1163   2-Et-Ph       NH          F1            NH          OH            H   H1164   2-Et-Ph       NH          F2            NH          OH            H   H1165   2-Et-Ph       NH          F3            NH          OH            H   H1166   2-Et-Ph       NH          F4            NH          OH            H   H1167   2-Et-Ph       NH          F5            NH          OH            H   H1168   2-Et-Ph       NH          F6            NH          OH            H   H1169   2-Et-Ph       NH          F7            NH          OH            H   H1170   2-Et-Ph       NH          F8            NH          OH            H   H1171   2-Et-Ph       NH          F9            NH          OH            H   H1172   2-Et-Ph       NH          F10           NH          OH            H   H1173   2-Et-Ph       NH          Ph            NH          OH            H   H1174   2-Et-Ph       NH          Bn            NH          OH            H   H1175   2-Et-Ph       NH          Pe            NH          OH            H   H1176   2-Et-Ph       NH          C12           NMe         OH            H   H1177   2-Et-Ph       NH          C12           NEt         OH            H   H1178   2-Et-Ph       NH          C12           NPr         OH            H   H1179   2-Et-Ph       NH          (CH2)3     N           OH            H   H1180   2-Et-Ph       NH          (CH2)4     N           OH            H   H1181   2-Et-Ph       NH          (CH2)5     N           OH            H   H1182   2-Et-Ph       NH           C12          O           OH            H   H1183   2-Et-Ph       NH           Ph           O           OH            H   H1184   2-Et-Ph       NH           C12          S           OH            H   H1185   2-Et-Ph       NH           Ph           S           OH            H   H1186   2-Et-Ph       NMe          H            NH          OH            H   H1187   2-Et-Ph       NEt          H            NH          OH            H   H1188   2-Et-Ph       NPr          H            NH          OH            H   H1189   2-Et-Ph       O            H            NH          OH            H   H1190   2-Et-Ph       S            H            NH          OH            H   H1191   2-Pr-Ph       NH           H            NH          H             H   H1192   2-Pr-Ph       NH          H            NH          OH            H    H1193   2-Pr-Ph       NH          H            NH          OA6           H    H1194   2-Pr-Ph       NH          H            NH          OA8           H    H1195   2-Pr-Ph       NH          H            NH          OA9           H    H1196   2-Pr-Ph       NH          H            NH          OA10          H    H1197   2-Pr-Ph       NH          H            NH          OA12          H    H1198   2-Pr-Ph       NH          H            NH          OA14          H    H1199   2-Pr-Ph       NH          H            NH          OA16          H    H1200   2-Pr-Ph       NH          H            NH          OH            H    A61201   2-Pr-Ph       NH          H            NH          OH            H    A81202   2-Pr-Ph       NH          H            NH          OH            H    A91203   2-Pr-Ph       NH          H            NH          OH            H    A101204   2-Pr-Ph       NH          H            NH          OH            H    A121205   2-Pr-Ph       NH          H            NH          OH            H    A141206   2-Pr-Ph       NH          H            NH          OH            H    A161207   2-Pr-Ph       NH          H            NH          OH            A6   A61208   2-Pr-Ph       NH          H            NH          OH            A8   A81209   2-Pr-Ph       NH          H            NH          OH            A10  A101210   2-Pr-Ph       NH          H            NH          OA2           A2   A21211   2-Pr-Ph       NH          H            NH          OA3           A3   A31212   2-Pr-Ph       NH          H            NH          OA4           A4   A41213   2-Pr-Ph       NH          H            NH          OC6           H    H1214   2-Pr-Ph       NH          H            NH          OC7           H    H1215   2-Pr-Ph       NH          H            NH          OC8           H    H1216   2-Pr-Ph       NH          H            NH          OC10          H    H1217   2-Pr-Ph       NH          H            NH          OC11          H    H1218   2-Pr-Ph       NH          H            NH          OC12          H    H1219   2-Pr-Ph       NH          H            NH          OC14          H    H1220   2-Pr-Ph       NH          H            NH          OC16          H    H1221  2-Pr-Ph         NH   H               NH         C6CO3           H    H1222  2-Pr-Ph         NH   H               NH         C7CO3           H    H1223  2-Pr-Ph         NH   H               NH         C8CO3           H    H1224  2-Pr-Ph         NH   H               NH         C9CO3           H    H1225  2-Pr-Ph         NH   H               NH         C10CO3          H    H1226  2-Pr-Ph         NH   H               NH         C12CO3          H    H1227  2-Pr-Ph         NH   H               NH         C16CO3          H    H1228  2-Pr-Ph         NH   C8              NH         OH               H    H1229  2-Pr-Ph         NH   C9              NH         OH               H    H1230  2-Pr-Ph         NH   C10             NH         OH               H    H1231  2-Pr-Ph         NH   C12             NH         OH               H    H1232  2-Pr-Ph         NH   C16             NH         OH               H    H1233  2-Pr-Ph         NH   F1              NH         OH               H    H1234  2-Pr-Ph         NH   F2              NH         OH               H    H1235  2-Pr-Ph         NH   F3              NH         OH               H    H1236  2-Pr-Ph         NH   F4              NH         OH               H    H1237  2-Pr-Ph         NH   F5              NH         OH               H    H1238  2-Pr-Ph         NH   F6              NH         OH               H    H1239  2-Pr-Ph         NH   F7              NH         OH               H    H1240  2-Pr-Ph         NH   F8              NH         OH               H    H1241  2-Pr-Ph         NH   F9              NH         OH               H    H1242  2-Pr-Ph         NH   F10             NH         OH               H    H1243  2-Pr-Ph         NH   Ph              NH         OH               H    H1244  2-Pr-Ph         NH   Bn              NH         OH               H    H1245  2-Pr-Ph         NH   Pe              NH         OH               H    H1246  2-Pr-Ph         NH   C12             NMe        OH               H    H1247  2-Pr-Ph         NH   C12             NEt        OH               H    H1248  2-Pr-Ph         NH   C12             NPr        OH               H    H1249  2-Pr-Ph         NH   (CH2)3       N          OH               H    H1250  2-Pr-Ph        NH          (CH2)4     N    OH            H   H1251  2-Pr-Ph        NH          (CH2)5     N    OH            H   H1252  2-Pr-Ph        NH          C12           O    OH            H   H1253  2-Pr-Ph        NH          Ph            O    OH            H   H1254  2-Pr-Ph        NH          C12           S    OH            H   H1255  2-Pr-Ph        NH          Ph            S    OH            H   H1256  2-Pr-Ph        NMe         H             NH   OH            H   H1257  2-Pr-Ph        NEt         H             NH   OH            H   H1258  2-Pr-Ph        NPr         H             NH   OH            H   H1259  2-Pr-Ph        O           H             NH   OH            H   H1260  2-Pr-Ph        S           H             NH   OH            H   H1261  2-iPr-Ph       NH          H             NH   H             H   H1262  2-iPr-Ph       NH          H             NH   OH            H   H1263  2-iPr-Ph       NH          H             NH   OA6           H   H1264  2-iPr-Ph       NH          H             NH   OA8           H   H1265  2-iPr-Ph       NH          H             NH   OA9           H   H1266  2-iPr-Ph       NH          H             NH   OA10          H   H1267  2-iPr-Ph       NH          H             NH   OA12          H   H1268  2-iPr-Ph       NH          H             NH   OA14          H   H1269  2-iPr-Ph       NH          H             NH   OA16          H   H1270  2-iPr-Ph       NH          H             NH   OH            H   A61271  2-iPr-Ph       NH          H             NH   OH            H   A81272  2-iPr-Ph       NH          H             NH   OH            H   A91273  2-iPr-Ph       NH          H             NH   OH            H   A101274  2-iPr-Ph       NH          H             NH   OH            H   A121275  2-iPr-Ph       NH          H             NH   OH            H   A141276  2-iPr-Ph       NH          H             NH   OH            H   A161277  2-iPr-Ph       NH          H             NH   OH            A6  A61278  2-iPr-Ph       NH          H             NH   OH            A8  A81279  2-iPr-Ph       NH           H             NH   OH              A10  A101280  2-iPr-Ph       NH           H             NH   OA2             A2   A21281  2-iPr-Ph       NH           H             NH   OA3             A3   A31282  2-iPr-Ph       NH           H             NH   OA4             A4   A41283  2-iPr-Ph       NH           H             NH   OC6             H    H1284  2-iPr-Ph       NH           H             NH   OC7             H    H1285  2-iPr-Ph       NH           H             NH   OC8             H    H1286  2-iPr-Ph       NH           H             NH   OC10            H    H1287  2-iPr-Ph       NH           H             NH   OC11            H    H1288  2-iPr-Ph       NH           H             NH   OC12            H    H1289  2-iPr-Ph       NH           H             NH   OC14            H    H1290  2-iPr-Ph       NH           H             NH   OC16            H    H1291  2-iPr-Ph       NH           H             NH   C6CO3          H    H1292  2-iPr-Ph       NH           H             NH   C7CO3          H    H1293  2-iPr-Ph       NH           H             NH   C8CO3          H    H1294  2-iPr-Ph       NH           H             NH   C9CO3          H    H1295  2-iPr-Ph       NH           H             NH   C10CO3         H    H1296  2-iPr-Ph       NH           H             NH   C12CO3         H    H1297  2-iPr-Ph       NH           H             NH   C16CO3         H    H1298  2-iPr-Ph       NH           C8            NH   OH              H    H1299  2-iPr-Ph       NH           C9            NH   OH              H    H1300  2-iPr-Ph       NH           C10           NH   OH              H    H1301  2-iPr-Ph       NH           C12           NH   OH              H    H1302  2-iPr-Ph       NH           C16           NH   OH              H    H1303  2-iPr-Ph       NH           F1            NH   OH              H    H1304  2-iPr-Ph       NH           F2            NH   OH              H    H1305  2-iPr-Ph       NH           F3            NH   OH              H    H1306  2-iPr-Ph       NH           F4            NH   OH              H    H1307  2-iPr-Ph       NH           F5            NH   OH              H    H1308  2-iPr-Ph       NH          F6            NH   OH            H   H1309  2-iPr-Ph       NH          F7            NH   OH            H   H1310  2-iPr-Ph       NH          F8            NH   OH            H   H1311  2-iPr-Ph       NH          F9            NH   OH            H   H1312  2-iPr-Ph       NH          F10           NH   OH            H   H1313  2-iPr-Ph       NH          Ph            NH   OH            H   H1314  2-iPr-Ph       NH          Bn            NH   OH            H   H1315  2-iPr-Ph       NH          Pe            NH   OH            H   H1316  2-iPr-Ph       NH          C12           NMe  OH            H   H1317  2-iPr-Ph       NH          C12           NEt  OH            H   H1318  2-iPr-Ph       NH          C12           NPr  OH            H   H1319  2-iPr-Ph       NH          (CH2)3     N    OH            H   H1320  2-iPr-Ph       NH          (CH2)4     N    OH            H   H1321  2-iPr-Ph       NH          (CH2)5     N    OH            H   H1322  2-iPr-Ph       NH          C12           O    OH            H   H1323  2-iPr-Ph       NH          Ph            O    OH            H   H1324  2-iPr-Ph       NH          C12           S    OH            H   H1325  2-iPr-Ph       NH          Ph            S    OH            H   H1326  2-iPr-Ph       NMe         H             NH   OH            H   H1327  2-iPr-Ph       NEt         H             NH   OH            H   H1328  2-iPr-Ph       NPr         H             NH   OH            H   H1329  2-iPr-Ph       O           H             NH   OH            H   H1330  2-iPr-Ph       S           H             NH   OH            H   H1331  2-Bu-Ph        NH          H             NH   H             H   H1332  2-Bu-Ph        NH          H             NH   OH            H   H1333  2-Bu-Ph        NH          H             NH   OA6           H   H1334  2-Bu-Ph        NH          H             NH   OA8           H   H1335  2-Bu-Ph        NH          H             NH   OA9           H   H1336  2-Bu-Ph        NH          H             NH   OA10          H   H1337  2-Bu-Ph         NH   H             NH           OA12            H    H1338  2-Bu-Ph         NH   H             NH           OA14            H    H1339  2-Bu-Ph         NH   H             NH           OA16            H    H1340  2-Bu-Ph         NH   H             NH           OH              H    A61341  2-Bu-Ph         NH   H             NH           OH              H    A81342  2-Bu-Ph         NH   H             NH           OH              H    A91343  2-Bu-Ph         NH   H             NH           OH              H    A101344  2-Bu-Ph         NH   H             NH           OH              H    A121345  2-Bu-Ph         NH   H             NH           OH              H    A141346  2-Bu-Ph         NH   H             NH           OH              H    A161347  2-Bu-Ph         NH   H             NH           OH              A6   A61348  2-Bu-Ph         NH   H             NH           OH              A8   A81349  2-Bu-Ph         NH   H             NH           OH              A10  A101350  2-Bu-Ph         NH   H             NH           OA2             A2   A221351  2-Bu-Ph         NH   H             NH           OA3             A3   A31352  2-Bu-Ph         NH   H             NH           OA4             A4   A41353  2-Bu-Ph         NH   H             NH           OC6             H    H1354  2-Bu-Ph         NH   H             NH           OC7             H    H1355  2-Bu-Ph         NH   H             NH           OC8             H    H1356  2-Bu-Ph         NH   H             NH           OC10            H    H1357  2-Bu-Ph         NH   H             NH           OC11            H    H1358  2-Bu-Ph         NH   H             NH           OC12            H    H1359  2-Bu-Ph         NH   H             NH           OC14            H    H1360  2-Bu-Ph         NH   H             NH           OC16            H    H1361  2-Bu-Ph         NH   H             NH           C6CO3          H    H1362  2-Bu-Ph         NH   H             NH           C7CO3          H    H1363  2-Bu-Ph         NH   H             NH           C8CO3          H    H1364  2-Bu-Ph         NH   H             NH           C9CO3          H    H1365  2-Bu-Ph         NH   H             NH           C10CO3         H    H1366 2-Bu-Ph       NH          H             NH          C12CO3       H   H1367 2-Bu-Ph       NH          H             NH          C16CO3       H   H1368 2-Bu-Ph       NH          C8            NH          OH            H   H1369 2-Bu-Ph       NH          C9            NH          OH            H   H1370 2-Bu-Ph       NH          C10           NH          OH            H   H1371 2-Bu-Ph       NH          C12           NH          OH            H   H1372 2-Bu-Ph       NH          C16           NH          OH            H   H1373 2-Bu-Ph       NH          F1            NH          OH            H   H1374 2-Bu-Ph       NH          F2            NH          OH            H   H1375 2-Bu-Ph       NH          F3            NH          OH            H   H1376 2-Bu-Ph       NH          F4            NH          OH            H   H1377 2-Bu-Ph       NH          F5            NH          OH            H   H1378 2-Bu-Ph       NH          F6            NH          OH            H   H1379 2-Bu-Ph       NH          F7            NH          OH            H   H1380 2-Bu-Ph       NH          F8            NH          OH            H   H1381 2-Bu-Ph       NH          F9            NH          OH            H   H1382 2-Bu-Ph       NH          F10           NH          OH            H   H1383 2-Bu-Ph       NH          Ph            NH          OH            H   H1384 2-Bu-Ph       NH          Bn            NH          OH            H   H1385 2-Bu-Ph       NH          Pe            NH          OH            H   H1386 2-Bu-Ph       NH          C12           NMe         OH            H   H1387 2-Bu-Ph       NH          C12           NEt         OH            H   H1388 2-Bu-Ph       NH          C12           NPr         OH            H   H1389 2-Bu-Ph       NH          (CH2)3     N           OH            H   H1390 2-Bu-Ph       NH          (CH2)4     N           OH            H   H1391 2-Bu-Ph       NH          (CH2)5     N           OH            H   H1392 2-Bu-Ph       NH          C12           O           OH            H   H1393 2-Bu-Ph       NH          Ph            O           OH            H   H1394 2-Bu-Ph       NH          C12           S           OH            H   H1395 2-Bu-Ph         NH   Ph              S    OH               H    H1396 2-Bu-Ph         NMe  H               NH   OH               H    H1397 2-Bu-Ph         NEt  H               NH   OH               H    H1398 2-Bu-Ph         NPr  H               NH   OH               H    H1399 2-Bu-Ph         O    H               NH   OH               H    H1400 2-Bu-Ph         S    H               NH   OH               H    H1401 4-Vin-Ph        NH   H               NH   H                H    H1402 4-Vin-Ph        NH   H               NH   OH               H    H1403 4-Vin-Ph        NH   H               NH   OA6              H    H1404 4-Vin-Ph        NH   H               NH   OA8              H    H1405 4-Vin-Ph        NH   H               NH   OA9              H    H1406 4-Vin-Ph        NH   H               NH   OA10             H    H1407 4-Vin-Ph        NH   H               NH   OA12             H    H1408 4-Vin-Ph        NH   H               NH   OA14             H    H1409 4-Vin-Ph        NH   H               NH   OA16             H    H1410 4-Vin-Ph        NH   H               NH   OH               H    A61411 4-Vin-Ph        NH   H               NH   OH               H    A81412 4-Vin-Ph        NH   H               NH   OH               H    A91413 4-Vin-Ph        NH   H               NH   OH               H    A101414 4-Vin-Ph        NH   H               NH   OH               H    A121415 4-Vin-Ph        NH   H               NH   OH               H    A141416 4-Vin-Ph        NH   H               NH   OH               H    A161417 4-Vin-Ph        NH   H               NH   OH               A6   A61418 4-Vin-Ph        NH   H               NH   OH               A8   A81419 4-Vin-Ph        NH   H               NH   OH               A10  A101420 4-Vin-Ph        NH   H               NH   OA2              A2   A21421 4-Vin-Ph        NH   H               NH   OA3              A3   A31422 4-Vin-Ph        NH   H               NH   OA4              A4   A41423 4-Vin-Ph        NH   H               NH   OC6              H    H1424 4-Vin-Ph       NH  H             NH            OC7               H   H1425 4-Vin-Ph       NH  H             NH            OC8               H   H1426 4-Vin-Ph       NH  H             NH            OC10              H   H1427 4-Vin-Ph       NH  H             NH            OC11              H   H1428 4-Vin-Ph       NH  H             NH            OC12              H   H1429 4-Vin-Ph       NH  H             NH            OC14              H   H1430 4-Vin-Ph       NH  H             NH            OC16              H   H1431 4-Vin-Ph       NH  H             NH            C6CO3            H   H1432 4-Vin-Ph       NH  H             NH            C7CO3            H   H1433 4-Vin-Ph       NH  H             NH            C8CO3            H   H1434 4-Vin-Ph       NH  H             NH            C9CO3            H   H1435 4-Vin-Ph       NH  H             NH            C10CO3           H   H1436 4-Vin-Ph       NH  H             NH            C12CO3           H   H1437 4-Vin-Ph       NH  H             NH            C16CO3           H   H1438 4-Vin-Ph       NH  C8            NH            OH                H   H1439 4-Vin-Ph       NH  C9            NH            OH                H   H1440 4-Vin-Ph       NH  C10           NH            OH                H   H1441 4-Vin-Ph       NH  C12           NH            OH                H   H1442 4-Vin-Ph       NH  C16           NH            OH                H   H1443 4-Vin-Ph       NH  F1            NH            OH                H   H1444 4-Vin-Ph       NH  F2            NH            OH                H   H1445 4-Vin-Ph       NH  F3            NH            OH                H   H1446 4-Vin-Ph       NH  F4            NH            OH                H   H1447 4-Vin-Ph       NH  F5            NH            OH                H   H1448 4-Vin-Ph       NH  F6            NH            OH                H   H1449 4-Vin-Ph       NH  F7            NH            OH                H   H1450 4-Vin-Ph       NH  F8            NH            OH                H   H1451 4-Vin-Ph       NH  F9            NH            OH                H   H1452 4-Vin-Ph       NH  F10           NH            OH                H   H1453 4-Vin-Ph       NH   Ph             NH           OH             H   H1454 4-Vin-Ph       NH   Bn             NH           OH             H   H1455 4-Vin-Ph       NH   Pe             NH           OH             H   H1456 4-Vin-Ph       NH   C12            NMe          OH             H   H1457 4-Vin-Ph       NH   C12            NEt          OH             H   H1458 4-Vin-Ph       NH   C12            NPr          OH             H   H1459 4-Vin-Ph       NH   (CH2)3      N            OH             H   H1460 4-Vin-Ph       NH   (CH2)4      N            OH             H   H1461 4-Vin-Ph       NH   (CH2)5      N            OH             H   H1462 4-Vin-Ph       NH   C12            O            OH             H   H1463 4-Vin-Ph       NH   Ph             O            OH             H   H1464 4-Vin-Ph       NH   C12            S            OH             H   H1465 4-Vin-Ph       NH   Ph             S            OH             H   H1466 4-Vin-Ph       NMe  H              NH           OH             H   H1467 4-Vin-Ph       NEt  H              NH           OH             H   H1468 4-Vin-Ph       NPr  H              NH           OH             H   H1469 4-Vin-Ph       O    H              NH           OH             H   H1470 4-Vin-Ph       S    H              NH           OH             H   H1471 4-CF3-Ph      NH   H              NH           H              H   H1472 4-CF3-Ph      NH   H              NH           OH             H   H1473 4-CF3-Ph      NH   H              NH           OA6            H   H1474 4-CF3-Ph      NH   H              NH           OA8            H   H1475 4-CF3-Ph      NH   H              NH           OA9            H   H1476 4-CF3-Ph      NH   H              NH           OA10           H   H1477 4-CF3-Ph      NH   H              NH           OA12           H   H1478 4-CF3-Ph      NH   H              NH           OA14           H   H1479 4-CF3-Ph      NH   H              NH           OA16           H   H1480 4-CF3-Ph      NH   H              NH           OH             H   A61481 4-CF3-Ph      NH   H              NH           OH             H   A81482 4-CF3-Ph         NH   H      NH            OH               H    A91483 4-CF3-Ph         NH   H      NH            OH               H    A101484 4-CF3-Ph         NH   H      NH            OH               H    A121485 4-CF3-Ph         NH   H      NH            OH               H    A141486 4-CF3-Ph         NH   H      NH            OH               H    A161487 4-CF3-Ph         NH   H      NH            OH               A6   A61488 4-CF3-Ph         NH   H      NH            OH               A8   A81489 4-CF3-Ph         NH   H      NH            OH               A10  A101490 4-CF3-Ph         NH   H      NH            OA2              A2   A21491 4-CF3-Ph         NH   H      NH            OA3              A3   A31492 4-CF3-Ph         NH   H      NH            OA4              A4   A41493 4-CF3-Ph         NH   H      NH            OC6              H    H1494 4-CF3-Ph         NH   H      NH            OC7              H    H1495 4-CF3-Ph         NH   H      NH            OC8              H    H1496 4-CF3-Ph         NH   H      NH            OC10             H    H1497 4-CF3-Ph         NH   H      NH            OC11             H    H1498 4-CF3-Ph         NH   H      NH            OC12             H    H1499 4-CF3-Ph         NH   H      NH            OC14             H    H1500 4-CF3-Ph         NH   H      NH            OC16             H    H1501 4-CF3-Ph         NH   H      NH            C6CO3           H    H1502 4-CF3-Ph         NH   H      NH            C7CO3           H    H1503 4-CF3-Ph         NH   H      NH            C8CO3           H    H1504 4-CF3-Ph         NH   H      NH            C9CO3           H    H1505 4-CF3-Ph         NH   H      NH            C10CO3          H    H15O6 4-CF3-Ph         NH   H      NH            C12CO3          H    H1507 4-CF3-Ph         NH   H      NH            C16CO3          H    H1508 4-CF3-Ph         NH   C8     NH            OH               H    H1509 4-CF3-Ph         NH   C9     NH            OH               H    H1510 4-CF3-Ph         NH   C10    NH            OH               H    H1511 4-CF3-Ph       NH          C12           NH   OH            H   H1512 4-CF3-Ph       NH          C16           NH   OH            H   H1513 4-CF3-Ph       NH          F1            NH   OH            H   H1514 4-CF3-Ph       NH          F2            NH   OH            H   H1515 4-CF3-Ph       NH          F3            NH   OH            H   H1516 4-CF3-Ph       NH          F4            NH   OH            H   H1517 4-CF3-Ph       NH          F5            NH   OH            H   H1518 4-CF3-Ph       NH          F6            NH   OH            H   H1519 4-CF3-Ph       NH          F7            NH   OH            H   H1520 4-CF3-Ph       NH          F8            NH   OH            H   H1521 4-CF3-Ph       NH          F9            NH   OH            H   H1522 4-CF3-Ph       NH          F10           NH   OH            H   H1523 4-CF3-Ph       NH          Ph            NH   OH            H   H1524 4-CF3-Ph       NH          Bn            NH   OH            H   H1525 4-CF3-Ph       NH          Pe            NH   OH            H   H1526 4-CF3-Ph       NH          C12           NMe  OH            H   H1527 4-CF3-Ph       NH          C12           NEt  OH            H   H1528 4-CF3-Ph       NH          C12           NPr  OH            H   H1529 4-CF3-Ph       NH          (CH2)3     N    OH            H   H1530 4-CF3-Ph       NH          (CH2)4     N    OH            H   H1531 4-CF3-Ph       NH          (CH2)5     N    OH            H   H1532 4-CF3-Ph       NH          C12           O    OH            H   H1533 4-CF3-Ph       NH          Ph            O    OH            H   H1534 4-CF3-Ph       NH          C12           S    OH            H   H1535 4-CF3-Ph       NH          Ph            S    OH            H   H1536 4-CF3-Ph       NMe         H             NH   OH            H   H1537 4-CF3-Ph       NEt         H             NH   OH            H   H1538 4-CF3-Ph       NPr         H             NH   OH            H   H1539 4-CF3-Ph       O           H             NH   OH            H   H1540 4-CF3-Ph         S            H     NH           OH              H    H1541 2,4-Me2-Ph      NH           H     NH           H               H    H1542 2,4-Me2-Ph      NH           H     NH           OH              H    H1543 2,4-Me2-Ph      NH           H     NH           OA6             H    H1544 2,4-Me2-Ph      NH           H     NH           OA8             H    H1545 2,4-Me2-Ph      NH           H     NH           OA9             H    H1546 2,4-Me2-Ph      NH           H     NH           OA10            H    H1547 2,4-Me2-Ph      NH           H     NH           OA12            H    H1548 2,4-Me2-Ph      NH           H     NH           OA14            H    H1549 2,4-Me2-Ph      NH           H     NH           OA16            H    H1550 2,4-Me2-Ph      NH           H     NH           OH              H    A61551 2,4-Me2-Ph      NH           H     NH           OH              H    A81552 2,4-Me2-Ph      NH           H     NH           OH              H    A91553 2,4-Me2-Ph      NH           H     NH           OH              H    A101554 2,4-Me2-Ph      NH           H     NH           OH              H    A121555 2,4-Me2-Ph      NH           H     NH           OH              H    A141556 2,4-Me2-Ph      NH           H     NH           OH              H    A161557 2,4-Me2-Ph      NH           H     NH           OH              A6   A61558 2,4-Me2-Ph      NH           H     NH           OH              A8   A81559 2,4-Me2-Ph      NH           H     NH           OH              A10  A101560 2,4-Me2-Ph      NH           H     NH           OA2             A2   A21561 2,4-Me2-Ph      NH           H     NH           OA3             A3   A31562 2,4-Me2-Ph      NH           H     NH           OA4             A4   A41563 2,4-Me2-Ph      NH           H     NH           OC6             H    H1564 2,4-Me2-Ph      NH           H     NH           OC7             H    H1565 2,4-Me2-Ph      NH           H     NH           OC8             H    H1566 2,4-Me2-Ph      NH           H     NH           OC10            H    H1567 2,4-Me2-Ph      NH           H     NH           OC11            H    H1568 2,4-Me2-Ph      NH           H     NH           OC12            H    H1569  2,4-Me2-Ph       NH         H      NH            OC14             H    H1570  2,4-Me2-Ph       NH         H      NH            OC16             H    H1571  2,4-Me2-Ph       NH         H      NH            C6CO3           H    H1572  2,4-Me2-Ph       NH         H      NH            C7CO3           H    H1573  2,4-Me2-Ph       NH         H      NH            C8CO3           H    H1574  2,4-Me2-Ph       NH         H      NH            C9CO3           H    H1575  2,4-Me2-Ph       NH         H      NH            C10CO3          H    H1576  2,4-Me2-Ph       NH         H      NH            C12CO3          H    H1577  2,4-Me2-Ph       NH         H      NH            C16CO3          H    H1578  2,4-Me2-Ph       NH         C8     NH            OH               H    H1579  2,4-Me2-Ph       NH         C9     NH            OH               H    H1580  2,4-Me2-Ph       NH         C10    NH            OH               H    H1581  2,4-Me2-Ph       NH         C12    NH            OH               H    H1582  2,4-Me2-Ph       NH         C16    NH            OH               H    H1583  2,4-Me2-Ph       NH         F1     NH            OH               H    H1584  2,4-Me2-Ph       NH         F2     NH            OH               H    H1585  2,4-Me2-Ph       NH         F3     NH            OH               H    H1586  2,4-Me2-Ph       NH         F4     NH            OH               H    H1587  2,4-Me2-Ph       NH         F5     NH            OH               H    H1588  2,4-Me2-Ph       NH         F6     NH            OH               H    H1589  2,4-Me2-Ph       NH         F7     NH            OH               H    H1590  2,4-Me2-Ph       NH         F8     NH            OH               H    H1591  2,4-Me2-Ph       NH         F9     NH            OH               H    H1592  2,4-Me2-Ph       NH         F10    NH            OH               H    H1593  2,4-Me2-Ph       NH         Ph     NH            OH               H    H1594  2,4-Me2-Ph       NH         Bn     NH            OH               H    H1595  2,4-Me2-Ph       NH         Pe     NH            OH               H    H1596  2,4-Me2-Ph       NH         C12    NMe           OH               H    H1597  2,4-Me2-Ph       NH         C12    NEt           OH               H    H1598 2,4-Me2-Ph       NH          C12          NPr         OH      H    H1599 2,4-Me2-Ph       NH          (CH2)3    N           OH      H    H1600 2,4-Me2-Ph       NH          (CH2)4    N           OH      H    H1601 2,4-Me2-Ph       NH          (CH2)5    N           OH      H    H1602 2,4-Me2-Ph       NH          C12          O           OH      H    H1603 2,4-Me2-Ph       NH          Ph           O           OH      H    H1604 2,4-Me2-Ph       NH          C12          S           OH      H    H1605 2,4-Me2-Ph       NH          Ph           S           OH      H    H1606 2,4-Me2-Ph       NMe         H            NH          OH      H    H1607 2,4-Me2-Ph       NEt         H            NH          OH      H    H1608 2,4-Me2-Ph       NPr         H            NH          OH      H    H1609 2,4-Me2-Ph       O           H            NH          OH      H    H1610 2,4-Me2-Ph       S           H            NH          OH      H    H1611 3,4-Me2-Ph       NH          H            NH          H       H    H1612 3,4-Me2-Ph       NH          H            NH          OH      H    H1613 3,4-Me2-Ph       NH          H            NH          OA6     H    H1614 3,4-Me2-Ph       NH          H            NH          OA8     H    H1615 3,4-Me2-Ph       NH          H            NH          OA9     H    H1616 3,4-Me2-Ph       NH          H            NH          OA10    H    H1617 3,4-Me2-Ph       NH          H            NH          OA12    H    H1618 3,4-Me2-Ph       NH          H            NH          OA14    H    H1619 3,4-Me2-Ph       NH          H            NH          OA16    H    H1620 3,4-Me2-Ph       NH          H            NH          OH      H    A61621 3,4-Me2-Ph       NH          H            NH          OH      H    A81622 3,4-Me2-Ph       NH          H            NH          OH      H    A91623 3,4-Me2-Ph       NH          H            NH          OH      H    A101624 3,4-Me2-Ph       NH          H            NH          OH      H    A121625 3,4-Me2-Ph       NH          H            NH          OH      H    A141626 3,4-Me2-Ph       NH          H            NH          OH      H    A161627 3,4-Me2-Ph       NH           H              NH           OH              A6   A61628 3,4-Me2-Ph       NH           H              NH           OH              A8   A81629 3,4-Me2-Ph       NH           H              NH           OH              A10  A101630 3,4-Me2-Ph       NH           H              NH           OA2             A2   A21631 3,4-Me2-Ph       NH           H              NH           OA3             A3   A31632 3,4-Me2-Ph       NH           H              NH           OA4             A4   A41633 3,4-Me2-Ph       NH           H              NH           OC6             H    H1634 3,4-Me2-Ph       NH           H              NH           OC7             H    H1635 3,4-Me2-Ph       NH           H              NH           OC8             H    H1636 3,4-Me2-Ph       NH           H              NH           OC10            H    H1637 3,4-Me2-Ph       NH           H              NH           OC11            H    H1638 3,4-Me2-Ph       NH           H              NH           OC12            H    H1639 3,4-Me2-Ph       NH           H              NH           OC14            H    H1640 3,4-Me2-Ph       NH           H              NH           OC16            H    H1641 3,4-Me2-Ph       NH           H              NH           C6CO3          H    H1642 3,4-Me2-Ph       NH           H              NH           C7CO3          H    H1643 3,4-Me2-Ph       NH           H              NH           C8CO3          H    H1644 3,4-Me2-Ph       NH           H              NH           C9CO3          H    H1645 3,4-Me2-Ph       NH           H              NH           C10CO3         H    H1646 3,4-Me2-Ph       NH           H              NH           C12CO3         H    H1647 3,4-Me2-Ph       NH           H              NH           C16CO3         H    H1648 3,4-Me2-Ph       NH           C8             NH           OH              H    H1649 3,4-Me2-Ph       NH           C9             NH           OH              H    H1650 3,4-Me2-Ph       NH           C10            NH           OH              H    H1651 3,4-Me2-Ph       NH           C12            NH           OH              H    H1652 3,4-Me2-Ph       NH           C16            NH           OH              H    H1653 3,4-Me2-Ph       NH           F1             NH           OH              H    H1654 3,4-Me2-Ph       NH           F2             NH           OH              H    H1655 3,4-Me2-Ph       NH           F3             NH           OH              H    H1656 3,4-Me2-Ph       NH          F4            NH   OH             H    H1657 3,4-Me2-Ph       NH          F5            NH   OH             H    H1658 3,4-Me2-Ph       NH          F6            NH   OH             H    H1659 3,4-Me2-Ph       NH          F7            NH   OH             H    H1660 3,4-Me2-Ph       NH          F8            NH   OH             H    H1661 3,4-Me2-Ph       NH          F9            NH   OH             H    H1662 3,4-Me2-Ph       NH          F10           NH   OH             H    H1663 3,4-Me2-Ph       NH          Ph            NH   OH             H    H1664 3,4-Me2-Ph       NH          Bn            NH   OH             H    H1665 3,4-Me2-Ph       NH          Pe            NH   OH             H    H1666 3,4-Me2-Ph       NH          C12           NHe  OH             H    H1667 3,4-Me2-Ph       NH          C12           NEt  OH             H    H1668 3,4-Me2-Ph       NH          C12           NPr  OH             H    H1669 3,4-Me2-Ph       NH          (CH2)3     N    OH             H    H1670 3,4-Me2-Ph       NH          (CH2)4     N    OH             H    H1671 3,4-Me2-Ph       NH          (CH2)5     N    OH             H    H1672 3,4-Me2-Ph       NH          C12           O    OH             H    H1673 3,4-Me2-Ph       NH          Ph            O    OH             H    H1674 3,4-Me2-Ph       NH          C12           S    OH             H    H1675 3,4-Me2-Ph       NH          Ph            S    OH             H    H1676 3,4-Me2-Ph       NMe         H             NH   OH             H    H1677 3,4-Me2-Ph       NEt         H             NH   OH             H    H1678 3,4-Me2-Ph       NPr         H             NH   OH             H    H1679 3,4-Me2-Ph       O           H             NH   OH             H    H1680 3,4-Me2-Ph       S           H             NH   OH             H    H1681 3,5-Me2-Ph       NH          H             NH   H              H    H1682 3,5-Me2-Ph       NH          H             NH   OH             H    H1683 3,5-Me2-Ph       NH          H             NH   OA6            H    H1684 3,5-Me2-Ph       NH          H             NH   OA8            H    H1685 3,5-Me2-Ph       NH   H            NH         OA9           H    H1686 3,5-Me2-Ph       NH   H            NH         OA10          H    H1687 3,5-Me2-Ph       NH   H            NH         OA12          H    H1688 3,5-Me2-Ph       NH   H            NH         OA14          H    H1689 3,5-Me2-Ph       NH   H            NH         OA16          H    H1690 3,5-Me2-Ph       NH   H            NH         OH            H    A61691 3,5-Me2-Ph       NH   H            NH         OH            H    A81692 3,5-Me2-Ph       NH   H            NH         OH            H    A91693 3,5-Me2-Ph       NH   H            NH         OH            H    A101694 3,5-Me2-Ph       NH   H            NH         OH            H    A121695 3,5-Me2-Ph       NH   H            NH         OH            H    A141696 3,5-Me2-Ph       NH   H            NH         OH            H    A161697 3,5-Me2-Ph       NH   H            NH         OH            A6   A61698 3,5-Me2-Ph       NH   H            NH         OH            A8   A81699 3,5-Me2-Ph       NH   H            NH         OH            A10  A101700 3,5-Me2-Ph       NH   H            NH         OA2           A2   A21701 3,5-Me2-Ph       NH   H            NH         OA3           A3   A31702 3,5-Me2-Ph       NH   H            NH         OA4           A4   A41703 3,5-Me2-Ph       NH   H            NH         OC6           H    H1704 3,5-Me2-Ph       NH   H            NH         OC7           H    H1705 3,5-Me2-Ph       NH   H            NH         OC8           H    H1706 3,5-Me2-Ph       NH   H            NH         OC10          H    H1707 3,5-Me2-Ph       NH   H            NH         OC11          H    H1708 3,5-Me2-Ph       NH   H            NH         OC12          H    H1709 3,5-Me2-Ph       NH   H            NH         OC14          H    H1710 3,5-Me2-Ph       NH   H            NH         OC16          H    H1711 3,5-Me2-Ph       NH   H            NH         C6CO3        H    H1712 3,5-Me2-Ph       NH   H            NH         C7CO3        H    H1713 3,5-Me2-Ph       NH   H            NH         C8CO3        H    H1714 3,5-Me2-Ph     NH           H              NH   C9CO3          H    H1715 3,5-Me2-Ph     NH           H              NH   C10CO3         H    H1716 3,5-Me2-Ph     NH           H              NH   C12CO3         H    H1717 3,5-Me2-Ph     NH           H              NH   C16CO3         H    H1718 3,5-Me2-Ph     NH           C8             NH   OH              H    H1719 3,5-Me2-Ph     NH           C9             NH   OH              H    H1720 3,5-Me2-Ph     NH           C10            NH   OH              H    H1721 3,5-Me2-Ph     NH           C12            NH   OH              H    H1722 3,5-Me2-Ph     NH           C16            NH   OH              H    H1723 3,5-Me2-Ph     NH           F1             NH   OH              H    H1724 3,5-Me2-Ph     NH           F2             NH   OH              H    H1725 3,5-Me2-Ph     NH           F3             NH   OH              H    H1726 3,5-Me2-Ph     NH           F4             NH   OH              H    H1727 3,5-Me2-Ph     NH           F5             NH   OH              H    H1728 3,5-Me2-Ph     NH           F6             NH   OH              H    H1729 3,5-Me2-Ph     NH           F7             NH   OH              H    H1730 3,5-Me2-Ph     NH           F8             NH   OH              H    H1731 3,5-Me2-Ph     NH           F9             NH   OH              H    H1732 3,5-Me2-Ph     NH           F10            NH   OH              H    H1733 3,5-Me2-Ph     NH           Ph             NH   OH              H    H1734 3,5-Me2-Ph     NH           Bn             NH   OH              H    H1735 3,5-Me2-Ph     NH           Pe             NH   OH              H    H1736 3,5-Me2-Ph     NH           C12            NMe  OH              H    H1737 3,5-Me2-Ph     NH           C12            NEt  OH              H    H1738 3,5-Me2-Ph     NH           C12            NPr  OH              H    H1739 3,5-Me2-Ph     NH           (CH2)3      N    OH              H    H1740 3,5-Me2-Ph     NH           (CH2)4      N    OH              H    H1741 3,5-Me2-Ph     NH           (CH2)5      N    OH              H    H1742 3,5-Me2-Ph     NH           C12            O    OH              H    H1743 3,5-Me2-Ph        NH   Ph           O    OH            H    H1744 3,5-Me2-Ph        NH   C12          S    OH            H    H1745 3,5-Me2-Ph        NH   Ph           S    OH            H    H1746 3,5-Me2-Ph        NMe  H            NH   OH            H    H1747 3,5-Me2-Ph        NEt  H            NH   OH            H    H1748 3,5-Me2-Ph        NPr  H            NH   OH            H    H1749 2,4,6-Me3-Ph     O    H            NH   OH            H    H1750 2,4,6-Me3-Ph     S    H            NH   OH            H    H1751 2,4,6-Me3-Ph     NH   H            NH   H             H    H1752 2,4,6-Me3-Ph     NH   H            NH   OH            H    H1753 2,4,6-Me3-Ph     NH   H            NH   OA6           H    H1754 2,4,6-Me3-Ph     NH   H            NH   OA8           H    H1755 2,4,6-Me3-Ph     NH   H            NH   OA9           H    H1756 2,4,6-Me3-Ph     NH   H            NH   OA10          H    H1757 2,4,6-Me3-Ph     NH   H            NH   OA12          H    H1758 2,4,6-Me3-Ph     NH   H            NH   OA14          H    H1759 2,4,6-Me3-Ph     NH   H            NH   OA16          H    H1760 2,4,6-Me3-Ph     NH   H            NH   OH            H    A61761 2,4,6-Me3-Ph     NH   H            NH   OH            H    A81762 2,4,6-Me3-Ph     NH   H            NH   OH            H    A91763 2,4,6-Me3-Ph     NH   H            NH   OH            H    A101764 2,4,6-Me3-Ph     NH   H            NH   OH            H    A121765 2,4,6-Me3-Ph     NH   H            NH   OH            H    A141766 2,4,6-Me3-Ph     NH   H            NH   OH            H    A161767 2,4,6-Me3-Ph     NH   H            NH   OH            A6   A61768 2,4,6-Me3-Ph     NH   H            NH   OH            A8   A81769 2,4,6-Me3-Ph     NH   H            NH   OH            A10  A101770 2,4,6-Me3-Ph     NH   H            NH   OA2           A2   A21771 2,4,6-Me3-Ph     NH   H            NH   OA3           A3   A31772 2,4,6-Me3-Ph     NH        H           NH        OA4          A4   A41773 2,4,6-Me3-Ph     NH        H           NH        OC6          H    H1774 2,4,6-Me3-Ph     NH        H           NH        OC7          H    H1775 2,4,6-Me3-Ph     NH        H           NH        OC8          H    H1776 2,4,6-Me3-Ph     NH        H           NH        OC10         H    H1777 2,4,6-Me3-Ph     NH        H           NH        OC11         H    H1778 2,4,6-Me3-Ph     NH        H           NH        OC12         H    H1779 2,4,6-Me3-Ph     NH        H           NH        OC14         H    H1780 2,4,6-Me3-Ph     NH        H           NH        OC16         H    H1781 2,4,6-Me3-Ph     NH        H           NH        C6CO3       H    H1782 2,4,6-Me3-Ph     NH        H           NH        C7CO3       H    H1783 2,4,6-Me3-Ph     NH        H           NH        C8CO3       H    H1784 2,4,6-Me3-Ph     NH        H           NH        C9CO3       H    H1785 2,4,6-Me3-Ph     NH        H           NH        C10CO3      H    H1786 2,4,6-Me3-Ph     NH        H           NH        C12CO3      H    H1787 2,4,6-Me3-Ph     NH        H           NH        C16CO3      H    H1788 2,4,6-Me3-Ph     NH        C8          NH        OH           H    H1789 2,4,6-Me3-Ph     NH        C9          NH        OH           H    H1790 2,4,6-Me3-Ph     NH        C10         NH        OH           H    H1791 2,4,6-Me3-Ph     NH        C12         NH        OH           H    H1792 2,4,6-Me3-Ph     NH        C16         NH        OH           H    H1793 2,4,6-Me3-Ph     NH        F1          NH        OH           H    H1794 2,4,6-Me3-Ph     NH        F2          NH        OH           H    H1795 2,4,6-Me3-Ph     NH        F3          NH        OH           H    H1796 2,4,6-Me3-Ph     NH        F4          NH        OH           H    H1797 2,4,6-Me3-Ph     NH        F5          NH        OH           H    H1798 2,4,6-Me3-Ph     NH        F6          NH        OH           H    H1799 2,4,6-Me3-Ph     NH        F7          NH        OH           H    H1800 2,4,6-Me3-Ph     NH        F8          NH        OH           H    H1801 2,4,6-Me3-Ph     NH   F9           NH         OH           H    H1802 2,4,6-Me3-Ph     NH   F10          NH         OH           H    H1803 2,4,6-Me3-Ph     NH   Ph           NH         OH           H    H1804 2,4,6-Me3-Ph     NH   Bn           NH         OH           H    H1805 2,4,6-Me3-Ph     NH   Pe           NH         OH           H    H1806 2,4,6-Me3-Ph     NH   C12          NMe        OH           H    H1807 2,4,6-Me3-Ph     NH   C12          NEt        OH           H    H1808 2,4,6-Me3-Ph     NH   C12          NPr        OH           H    H1809 2,4,6-Me3-Ph     NH   (CH2)3    N          OH           H    H1810 2,4,6-Me3-Ph     NH   (CH2)4    N          OH           H    H1811 2,4,6-Me3-Ph     NH   (CH2)5    N          OH           H    H1812 2,4,6-Me3-Ph     NH   C12          O          OH           H    H1813 2,4,6-Me3-Ph     NH   Ph           O          OH           H    H1814 2,4,6-Me3-Ph     NH   C12          S          OH           H    H1815 2,4,6-Me3-Ph     NH   Ph           S          OH           H    H1816 2,4,6-Me3-Ph     NMe  H            NH         OH           H    H1817 2,4,6-Me3-Ph     NEt  H            NH         OH           H    H1818 2,4,6-Me3-Ph     NPr  H            NH         OH           H    H1819 2,4,6-Me3-Ph     O    H            NH         OH           H    H1820 2,4,6-Me3-Ph     S    H            NH         OH           H    H1821 2-MeO-Ph            NH   H            NH         H            H    H1822 2-MeO-Ph            NH   H            NH         OH           H    H1823 2-MeO-Ph            NH   H            NH         OA6          H    H1824 2-MeO-Ph            NH   H            NH         OA8          H    H1825 2-MeO-Ph            NH   H            NH         OA9          H    H1826 2-MeO-Ph            NH   H            NH         OA10         H    H1827 2-MeO-Ph            NH   H            NH         OA12         H    H1828 2-MeO-Ph            NH   H            NH         OA14         H    H1829 2-MeO-Ph            NH   H            NH         OA16         H    H1830 2-MeO-Ph       NH  H             NH           OH              H   A61831 2-MeO-Ph       NH  H             NH           OH              H   A81832 2-MeO-Ph       NH  H             NH           OH              H   A91833 2-MeO-Ph       NH  H             NH           OH              H   A101834 2-MeO-Ph       NH  H             NH           OH              H   A121835 2-MeO-Ph       NH  H             NH           OH              H   A141836 2-MeO-Ph       NH  H             NH           OH              H   A161837 2-MeO-Ph       NH  H             NH           OH              A6  A61838 2-MeO-Ph       NH  H             NH           OH              A8  A81839 2-MeO-Ph       NH  H             NH           OH              A10 A101840 2-MeO-Ph       NH  H             NH           OA2             A2  A21841 2-MeO-Ph       NH  H             NH           OA3             A3  A31842 2-MeO-Ph       NH  H             NH           OA4             A4  A41843 2-MeO-Ph       NH  H             NH           OC6             H   H1844 2-MeO-Ph       NH  H             NH           OC7             H   H1845 2-MeO-Ph       NH  H             NH           OC8             H   H1846 2-MeO-Ph       NH  H             NH           OC10            H   H1847 2-MeO-Ph       NH  H             NH           OC11            H   H1848 2-MeO-Ph       NH  H             NH           OC12            H   H1849 2-MeO-Ph       NH  H             NH           OC14            H   H1850 2-MeO-Ph       NH  H             NH           OC16            H   H1851 2-MeO-Ph       NH  H             NH           C6CO3          H   H1852 2-MeO-Ph       NH  H             NH           C7CO3          H   H1853 2-MeO-Ph       NH  H             NH           C8CO3          H   H1854 2-MeO-Ph       NH  H             NH           C9CO3          H   H1855 2-MeO-Ph       NH  H             NH           C10CO3         H   H1856 2-MeO-Ph       NH  H             NH           C12CO3         H   H1857 2-MeO-Ph       NH  H             NH           C16CO3         H   H1858 2-MeO-Ph       NH  C8            NH           OH              H   H1859 2-MeO-Ph      NH         C9           NH         OH           H   H1860 2-MeO-Ph      NH         C10          NH         OH           H   H1861 2-MeO-Ph      NH         C12          NH         OH           H   H1862 2-MeO-Ph      NH         C16          NH         OH           H   H1863 2-MeO-Ph      NH         F1           NH         OH           H   H1864 2-MeO-Ph      NH         F2           NH         OH           H   H1865 2-MeO-Ph      NH         F3           NH         OH           H   H1866 2-MeO-Ph      NH         F4           NH         OH           H   H1867 2-MeO-Ph      NH         F5           NH         OH           H   H1868 2-MeO-Ph      NH         F6           NH         OH           H   H1869 2-MeO-Ph      NH         F7           NH         OH           H   H1870 2-MeO-Ph      NH         F8           NH         OH           H   H1871 2-MeO-Ph      NH         F9           NH         OH           H   H1872 2-MeO-Ph      NH         F10          NH         OH           H   H1873 2-MeO-Ph      NH         Ph           NH         OH           H   H1874 2-MeO-Ph      NH         Bn           NH         OH           H   H1875 2-MeO-Ph      NH         Pe           NH         OH           H   H1876 2-MeO-Ph      NH         C12          NMe        OH           H   H1877 2-MeO-Ph      NH         C12          NEt        OH           H   H1878 2-MeO-Ph      NH         C12          NPr        OH           H   H1879 2-MeO-Ph      NH         (CH2)3    N          OH           H   H1880 2-MeO-Ph      NH         (CH2)4    N          OH           H   H1881 2-MeO-Ph      NH         (CH2)5    N          OH           H   H1882 2-MeO-Ph      NH         C12          O          OH           H   H1883 2-MeO-Ph      NH         Ph           O          OH           H   H1884 2-MeO-Ph      NH         C12          S          OH           H   H1885 2-MeO-Ph      NH         Ph           S          OH           H   H1886 2-MeO-Ph      NMe        H            NH         OH           H   H1887 2-MeO-Ph      NEt        H            NH         OH           H   H1888   2-MeO-Ph                 NPr     H            NH       OH            H         H1889   2-MeO-Ph                 O       H            NH       OH            H         H1890   2-MeO-Ph                 S       H            NH       OH            H         H1891   2-EtO-Ph                 NH      H            NH       H             H         H1892   2-EtO-Ph                 NH      H            NH       OH            H         H1893   2-EtO-Ph                 NH      H            NH       OA6           H         H1894   2-EtO-Ph                 NH      H            NH       OA8           H         H1895   2-EtO-Ph                 NH      H            NH       OA9           H         H1896   2-EtO-Ph                 NH      H            NH       OA10          H         H1897   2-EtO-Ph                 NH      H            NH       OA12          H         H1898   2-EtO-Ph                 NH      H            NH       OA14          H         H1899   2-EtO-Ph                 NH      H            NH       OA16          H         H1900   2-EtO-Ph                 NH      H            NH       OH            H         A61901   2-EtO-Ph                 NH      H            NH       OH            H         A81902   2-EtO-Ph                 NH      H            NH       OH            H         A91903   2-EtO-Ph                 NH      H            NH       OH            H         A101904   2-EtO-Ph                 NH      H            NH       OH            H         A121905   2-EtO-Ph                 NH      H            NH       OH            H         A141906   2-EtO-Ph                 NH      H            NH       OH            H         A161907   2-EtO-Ph                 NH      H            NH       OH            A6        A61908   2-EtO-Ph                 NH      H            NH       OH            A8        A81909   2-EtO-Ph                 NH      H            NH       OH            A10       A101910   2-EtO-Ph                 NH      H            NH       OA2           A2        A21911   2-EtO-Ph                 NH      H            NH       OA3           A3        A31912   2-EtO-Ph                 NH      H            NH       OA4           A4        A41913   2-EtO-Ph                 NH      H            NH       OC6           H         H1914   2-EtO-Ph                 NH      H            NH       OC7           H         H1915   2-EtO-Ph                 NH      H            NH       OC8           H         H1916   2-EtO-Ph                 NH      H            NH       OC10          H         H1917   2-EtO-Ph                 NH       H            NH       OC11         H         H1918   2-EtO-Ph                 NH       H            NH       OC12         H         H1919   2-EtO-Ph                 NH       H            NH       OC14         H         H1920   2-EtO-Ph                 NH       H            NH       OC16         H         H1921   2-EtO-Ph                 NH       H            NH       C6CO3       H         H1922   2-EtO-Ph                 NH       H            NH       C7CO3       H         H1923   2-EtO-Ph                 NH       H            NH       C8CO3       H         H1924   2-EtO-Ph                 NH       H            NH       C9CO3       H         H1925   2-EtO-Ph                 NH       H            NH       C10CO3      H         H1926   2-EtO-Ph                 NH       H            NH       C12CO3      H         H1927   2-EtO-Ph                 NH       H            NH       C16CO3      H         H1928   2-EtO-Ph                 NH       C8           NH       OH           H         H1929   2-EtO-Ph                 NH       C9           NH       OH           H         H1930   2-EtO-Ph                 NH       C10          NH       OH           H         H1931   2-EtO-Ph                 NH       C12          NH       OH           H         H1932   2-EtO-Ph                 NH       C16          NH       OH           H         H1933   2-EtO-Ph                 NH       F1           NH       OH           H         H1934   2-EtO-Ph                 NH       F2           NH       OH           H         H1935   2-EtO-Ph                 NH       F3           NH       OH           H         H1936   2-EtO-Ph                 NH       F4           NH       OH           H         H1937   2-EtO-Ph                 NH       F5           NH       OH           H         H1938   2-EtO-Ph                 NH       F6           NH       OH           H         H1939   2-EtO-Ph                 NH       F7           NH       OH           H         H1940   2-EtO-Ph                 NH       F8           NH       OH           H         H1941   2-EtO-Ph                 NH       F9           NH       OH           H         H1942   2-EtO-Ph                 NH       F10          NH       OH           H         H1943   2-EtO-Ph                 NH       Ph           NH       OH           H         H1944   2-EtO-Ph                 NH       Bn           NH       OH           H         H1945   2-EtO-Ph                 NH       Pe           NH       OH           H         H1946   2-EtO-Ph                 NH      C12          NMe      OH            H        H1947   2-EtO-Ph                 NH      C12          NEt      OH            H        H1948   2-EtO-Ph                 NH      C12          NPr      OH            H        H1949   2-EtO-Ph                 NH      (CH2)3    N        OH            H        H1950   2-EtO-Ph                 NH      (CH2)4    N        OH            H        H1951   2-EtO-Ph                 NH      (CH2)5    N        OH            H        H1952   2-EtO-Ph                 NH      C12          O        OH            H        H1953   2-EtO-Ph                 NH      Ph           O        OH            H        H1954   2-EtO-Ph                 NH      C12          S        OH            H        H1955   2-EtO-Ph                 NH      Ph           S        OH            H        H1956   2-EtO-Ph                 NMe     H            NH       OH            H        H1957   2-EtO-Ph                 NEt     H            NH       OH            H        H1958   2-EtO-Ph                 NPr     H            NH       OH            H        H1959   2-EtO-Ph                 O       H            NH       OH            H        H1960   2-EtO-Ph                 S       H            NH       OH            H        H1961   3-EtO-Ph                 NH      H            NH       H             H        H1962   3-EtO-Ph                 NH      H            NH       OH            H        H1963   3-EtO-Ph                 NH      H            NH       OA6           H        H1964   3-EtO-Ph                 NH      H            NH       OA8           H        H1965   3-EtO-Ph                 NH      H            NH       OA9           H        H1966   3-EtO-Ph                 NH      H            NH       OA10          H        H1967   3-EtO-Ph                 NH      H            NH       OA12          H        H1968   3-EtO-Ph                 NH      H            NH       OA14          H        H1969   3-EtO-Ph                 NH      H            NH       OA16          H        H1970   3-EtO-Ph                 NH      H            NH       OH            H        A61971   3-EtO-Ph                 NH      H            NH       OH            H        A81972   3-EtO-Ph                 NH      H            NH       OH            H        A91973   3-EtO-Ph                 NH      H            NH       OH            H        A101974   3-EtO-Ph                 NH      H            NH       OH            H        A121975   3-EtO-Ph                 NH       H            NH       OH            H        A141976   3-EtO-Ph                 NH       H            NH       OH            H        A161977   3-EtO-Ph                 NH       H            NH       OH            A6       A61978   3-EtO-Ph                 NH       H            NH       OH            A8       A81979   3-EtO-Ph                 NH       H            NH       OH            A10      A101980   3-EtO-Ph                 NH       H            NH       OA2           A2       A21981   3-EtO-Ph                 NH       H            NH       OA3           A3       A31982   3-EtO-Ph                 NH       H            NH       OA4           A4       A41983   3-EtO-Ph                 NH       H            NH       OC6           H        H1984   3-EtO-Ph                 NH       H            NH       OC7           H        H1985   3-EtO-Ph                 NH       H            NH       OC8           H        H1986   3-EtO-Ph                 NH       H            NH       OC10          H        H1987   3-EtO-Ph                 NH       H            NH       OC11          H        H1988   3-EtO-Ph                 NH       H            NH       OC12          H        H1989   3-EtO-Ph                 NH       H            NH       OC14          H        H1990   3-EtO-Ph                 NH       H            NH       OC16          H        H1991   3-EtO-Ph                 NH       H            NH       C6CO3        H        H1992   3-EtO-Ph                 NH       H            NH       C7CO3        H        H1993   3-EtO-Ph                 NH       H            NH       C8CO3        H        H1994   3-EtO-Ph                 NH       H            NH       C9CO3        H        H1995   3-EtO-Ph                 NH       H            NH       C10CO3       H        H1996   3-EtO-Ph                 NH       H            NH       C12CO3       H        H1997   3-EtO-Ph                 NH       H            NH       C16CO3       H        H1998   3-EtO-Ph                 NH       C8           NH       OH            H        H1999   3-EtO-Ph                 NH       C9           NH       OH            H        H2000   3-EtO-Ph                 NH       C10          NH       OH            H        H2001   3-EtO-Ph                 NH       C12          NH       OH            H        H2002   3-EtO-Ph                 NH       C16          NH       OH            H        H2003   3-EtO-Ph                 NH       F1           NH       OH            H        H2004 3-EtO-Ph       NH         F2          NH         OH           H   H2005 3-EtO-Ph       NH         F3          NH         OH           H   H2006 3-EtO-Ph       NH         F4          NH         OH           H   H2007 3-EtO-Ph       NH         F5          NH         OH           H   H2008 3-EtO-Ph       NH         F6          NH         OH           H   H2009 3-EtO-Ph       NH         F7          NH         OH           H   H2010 3-EtO-Ph       NH         F8          NH         OH           H   H2011 3-EtO-Ph       NH         F9          NH         OH           H   H2012 3-EtO-Ph       NH         F10         NH         OH           H   H2013 3-EtO-Ph       NH         Ph          NH         OH           H   H2014 3-EtO-Ph       NH         Bn          NH         OH           H   H2015 3-EtO-Ph       NH         Pe          NH         OH           H   H2016 3-EtO-Ph       NH         C12         NMe        OH           H   H2017 3-EtO-Ph       NH         C12         NEt        OH           H   H2018 3-EtO-Ph       NH         C12         NPr        OH           H   H2019 3-EtO-Ph       NH         (CH2)3   N          OH           H   H2020 3-EtO-Ph       NH         (CH2)4   N          OH           H   H2021 3-EtO-Ph       NH         (CH2)5   N          OH           H   H2022 3-EtO-Ph       NH         C12         O          OH           H   H2023 3-EtO-Ph       NH         Ph          O          OH           H   H2024 3-EtO-Ph       NH         C12         S          OH           H   H2025 3-EtO-Ph       NH         Ph          S          OH           H   H2026 3-EtO-Ph       NMe        H           NH         OH           H   H2027 3-EtO-Ph       NEt        H           NH         OH           H   H2028 3-EtO-Ph       NPr        H           NH         OH           H   H2029 3-EtO-Ph       O          H           NH         OH           H   H2030 3-EtO-Ph       S          H           NH         OH           H   H2031 4-EtO-Ph       NH         H           NH         H            H   H2032 4-EtO-Ph       NH         H           NH         OH           H   H2033 4-EtO-Ph       NH  H             NH           OA6             H   H2034 4-EtO-Ph       NH  H             NH           OA8             H   H2035 4-EtO-Ph       NH  H             NH           OA9             H   H2036 4-EtO-Ph       NH  H             NH           OA10            H   H2037 4-EtO-Ph       HH  H             NH           OA12            H   H2038 4-EtO-Ph       NH  H             NH           OA14            H   H2039 4-EtO-Ph       NH  H             NH           OA16            H   H2040 4-EtO-Ph       NH  H             NH           OH              H   A62041 4-EtO-Ph       NH  H             NH           OH              H   A82042 4-EtO-Ph       NH  H             NH           OH              H   A92043 4-EtO-Ph       NH  H             NH           OH              H   A102044 4-EtO-Ph       NH  H             NH           OH              H   A122045 4-EtO-Ph       NH  H             NH           OH              H   A142046 4-EtO-Ph       NH  H             NH           OH              H   A162047 4-EtO-Ph       NH  H             NH           OH              A6  A62048 4-EtO-Ph       NH  H             NH           OH              A8  A82049 4-EtO-Ph       NH  H             NH           OH              A10 A102050 4-EtO-Ph       NH  H             NH           OA2             A2  A22051 4-EtO-Ph       NH  H             NH           OA3             A3  A32052 4-EtO-Ph       NH  H             NH           OA4             A4  A42053 4-EtO-Ph       NH  H             NH           OC6             H   H2054 4-EtO-Ph       NH  H             NH           OC7             H   H2055 4-EtO-Ph       NH  H             NH           OC8             H   H2056 4-EtO-Ph       NH  H             NH           OC10            H   H2057 4-EtO-Ph       NH  H             NH           OC11            H   H2058 4-EtO-Ph       NH  H             NH           OC12            H   H2059 4-EtO-Ph       NH  H             NH           OC14            H   H2060 4-EtO-Ph       NH  H             NH           OC16            H   H2061 4-EtO-Ph       NH  H             NH           C6CO3          H   H2062 4-EtO-Ph       NH   H              NH            C7CO3          H   H2063 4-EtO-Ph       NH   H              NH            C8CO3          H   H2064 4-EtO-Ph       NH   H              NH            C9CO3          H   H2065 4-EtO-Ph       NH   H              NH            C10CO3         H   H2066 4-EtO-Ph       NH   H              NH            C12CO3         H   H2067 4-EtO-Ph       NH   H              NH            C16CO3         H   H2068 4-EtO-Ph       NH   C8             NH            OH              H   H2069 4-EtO-Ph       NH   C9             NH            OH              H   H2070 4-EtO-Ph       NH   C10            NH            OH              H   H2071 4-EtO-Ph       NH   C12            NH            OH              H   H2072 4-EtO-Ph       NH   C16            NH            OH              H   H2073 4-EtO-Ph       NH   F1             NH            OH              H   H2074 4-EtO-Ph       NH   F2             NH            OH              H   H2075 4-EtO-Ph       NH   F3             NH            OH              H   H2076 4-EtO-Ph       NH   F4             NH            OH              H   H2077 4-EtO-Ph       NH   F5             NH            OH              H   H2078 4-EtO-Ph       NH   F6             NH            OH              H   H2079 4-EtO-Ph       NH   F7             NH            OH              H   H2080 4-EtO-Ph       NH   F8             NH            OH              H   H2081 4-EtO-Ph       NH   F9             NH            OH              H   H2082 4-EtO-Ph       NH   F10            NH            OH              H   H2083 4-EtO-Ph       NH   Ph             NH            OH              H   H2084 4-EtO-Ph       NH   Bn             NH            OH              H   H2085 4-EtO-Ph       NH   Pe             NH            OH              H   H2086 4-EtO-Ph       NH   C12            NMe           OH              H   H2087 4-EtO-Ph       NH   C12            NEt           OH              H   H2088 4-EtO-Ph       NH   C12            NPr           OH              H   H2089 4-EtO-Ph       NH   (CH2)3      N             OH              H   H2090 4-EtO-Ph       NH   (CH2)4      N             OH              H   H2091 4-EtO-Ph       NH   (CH2)5   N         OH           H         H2092 4-EtO-Ph       NH   C12         O         OH           H         H2093 4-EtO-Ph       NH   Ph          O         OH           H         H2094 4-EtO-Ph       NH   C12         S         OH           H         H2095 4-EtO-Ph       NH   Ph          S         OH           H         H2096 4-EtO-Ph       NMe  H           NH        OH           H         H2097 4-EtO-Ph       NEt  H           NH        OH           H         H2098 4-EtO-Ph       NPr  H           NH        OH           H         H2099 4-EtO-Ph       O    H           NH        OH           H         H2100 4-EtO-Ph       S    H           NH        OH           H         H2101 3-iPrO-Ph      NH   H           NH        H            H         H2102 3-iPrO-Ph      NH   H           NH        OH           H         H2103 3-iPrO-Ph      NH   H           NH        OA6          H         H2104 3-iPrO-Ph      NH   H           NH        OA8          H         H2105 3-iPrO-Ph      NH   H           NH        OA9          H         H2106 3-iPrO-Ph      NH   H           NH        OA10         H         H2107 3-iPrO-Ph      NH   H           NH        OA12         H         H2108 3-iPrO-Ph      NH   H           NH        OA14         H         H2109 3-iPrO-Ph      NH   H           NH        OA16         H         H2110 3-iPrO-Ph      NH   H           NH        OH           H         A62111 3-iPrO-Ph      NH   H           NH        OH           H         A82112 3-iPrO-Ph      NH   H           NH        OH           H         A92113 3-iPrO-Ph      NH   H           NH        OH           H         A102114 3-iPrO-Ph      NH   H           NH        OH           H         A122115 3-iPrO-Ph      NH   H           NH        OH           H         A142116 3-iPrO-Ph      NH   H           NH        OH           H         A162117 3-iPrO-Ph      NH   H           NH        OH           A6        A62118 3-iPrO-Ph      NH   H           NH        OH           A8        A82119 3-iPrO-Ph      NH   H           NH        OH           A10       A102120 3-iPrO-Ph      NH   H            NH          OA2          A2  A22121 3-iPrO-Ph      NH   H            NH          OA3          A3  A32122 3-iPrO-Ph      NH   H            NH          OA4          A4  A42123 3-iPrO-Ph      NH   H            NH          OC6          H   H2124 3-iPrO-Ph      NH   H            NH          OC7          H   H2125 3-iPrO-Ph      NH   H            NH          OC8          H   H2126 3-iPrO-Ph      NH   H            NH          OC10         H   H2127 3-iPrO-Ph      NH   H            NH          OC11         H   H2128 3-iPrO-Ph      NH   H            NH          OC12         H   H2129 3-iPrO-Ph      NH   H            NH          OC14         H   H2130 3-iPrO-Ph      NH   H            NH          OC16         H   H2131 3-iPrO-Ph      NH   H            NH          C6CO3       H   H2132 3-iPrO-Ph      NH   H            NH          C7CO3       H   H2133 3-iPrO-Ph      NH   H            NH          C8CO3       H   H2134 3-iPrO-Ph      NH   H            NH          C9CO3       H   H2135 3-iPrO-Ph      NH   H            NH          C10CO3      H   H2136 3-iPrO-Ph      NH   H            NH          C12CO3      H   H2137 3-iPrO-Ph      NH   H            NH          C16CO3      H   H2138 3-iPrO-Ph      NH   C8           NH          OH           H   H2139 3-iPrO-Ph      NH   C9           NH          OH           H   H2140 3-iPrO-Ph      NH   C10          NH          OH           H   H2141 3-iPrO-Ph      NH   C12          NH          OH           H   H2142 3-iPrO-Ph      NH   C16          NH          OH           H   H2143 3-iPrO-Ph      NH   F1           NH          OH           H   H2144 3-iPrO-Ph      NH   F2           NH          OH           H   H2145 3-iPrO-Ph      NH   F3           NH          OH           H   H2146 3-iPrO-Ph      NH   F4           NH          OH           H   H2147 3-iPrO-Ph      NH   F5           NH          OH           H   H2148 3-iPrO-Ph      NH   F6           NH          OH           H   H2149 3-iPrO-Ph             NH  F7            NH  OH            H   H2150 3-iPrO-Ph             NH  F8            NH  OH            H   H2151 3-iPrO-Ph             NH  F9            NH  OH            H   H2152 3-iPrO-Ph             NH  F10           NH  OH            H   H2153 3-iPrO-Ph             NH  Ph            NH  OH            H   H2154 3-iPrO-Ph             NH  Bn            NH  OH            H   H2155 3-iPrO-Ph             NH  Pe            NH  OH            H   H2156 3-iPrO-Ph             NH  C12           NMe OH            H   H2157 3-iPrO-Ph             NH  C12           NEt OH            H   H2158 3-iPrO-Ph             NH  C12           NPr OH            H   H2159 3-iPrO-Ph             NH  (CH2)3     N   OH            H   H2160 3-iPrO-Ph             NH  (CH2)4     N   OH            H   H2161 3-iPrO-Ph             NH  (CH2)5     N   OH            H   H2162 3-iPrO-PH             NH   C12          O   OH            H   H2163 3-iPrO-Ph             NH   Ph           O   OH            H   H2164 3-iPrO-Ph             NH   C12          S   OH            H   H2165 3-iPrO-Ph             NH   Ph           S   OH            H   H2166 3-iPrO-Ph             NMe  H            NH  OH            H   H2167 3-iPrO-Ph             NEt  H            NH  OH            H   H2168 3-iPrO-Ph             NPr  H            NH  OH            H   H2169 3-iPrO-Ph             O    H            NH  OH            H   H2170 3-iPrO-Ph             S    H            NH  OH            H   H2171 4-iPrO-Ph             NH   H            NH  H             H   H2172 4-iPrO-Ph             NH   H            NH  OH            H   H2173 4-iPrO-Ph             NH   H            NH  OA6           H   H2174 4-iPrO-Ph             NH   H            NH  OA8           H   H2175 4-iPrO-Ph             NH   H            NH  OA9           H   H2176 4-iPrO-Ph             NH   H            NH  OA10          H   H2177 4-iPrO-Ph             NH   H            NH  OA12          H   H2178 4-iPrO-Ph      NH  H           NH         OA14          H          H2179 4-iPrO-Ph      NH  H           NH         OA16          H          H2180 4-iPrO-Ph      NH  H           NH         OH            H          A62181 4-iPrO-Ph      NH  H           NH         OH            H          A82182 4-iPrO-Ph      NH  H           NH         OH            H          A92183 4-iPrO-Ph      NH  H           NH         OH            H          A102184 4-iPrO-Ph      NH  H           NH         OH            H          A122185 4-iPrO-Ph      NH  H           NH         OH            H          A142186 4-iPrO-Ph      NH  H           NH         OH            H          A162187 4-iPrO-Ph      NH  H           NH         OH            A6         A62188 4-iPrO-Ph      NH  H           NH         OH            A8         A82189 4-iPrO-Ph      NH  H           NH         OH            A10        A102190 4-iPrO-Ph      NH  H           NH         OA2           A2         A22191 4-iPrO-Ph      NH  H           NH         OA3           A3         A32192 4-iPrO-Ph      NH  H           NH         OA4           A4         A42193 4-iPrO-Ph      NH  H           NH         OC6           H          H2194 4-iPrO-Ph      NH  H           NH         OC7           H          H2195 4-iPrO-Ph      NH  H           NH         OC8           H          H2196 4-iPrO-Ph      NH  H           NH         OC10          H          H2197 4-iPrO-Ph      NH  H           NH         OC11          H          H2198 4-iPrO-Ph      NH  H           NH         OC12          H          H2199 4-iPrO-Ph      NH  H           NH         OC14          H          H2200 4-iPrO-Ph      NH  H           NH         OC16          H          H2201 4-iPrO-Ph      NH  H           NH         C6CO3        H          H2202 4-iPrO-Ph      NH  H           NH         C7CO3        H          H2203 4-iPrO-Ph      NH  H           NH         C8CO3        H          H2204 4-iPrO-Ph      NH  H           NH         C9CO3        H          H2205 4-iPrO-Ph      NH  H           NH         C10CO3       H          H2206 4-iPrO-Ph      NH  H           NH         C12CO3       H          H2207       4-iPrO-Ph      NH  H               NH   C16CO3          H    H2208       4-iPrO-Ph      NH  C8              NH   OH               H    H2209       4-iPrO-Ph      NH  C9              NH   OH               H    H2210       4-iPrO-Ph      NH  C10             NH   OH               H    H2211       4-iPrO-Ph      NH  C12             NH   OH               H    H2212       4-iPrO-Ph      NH  C16             NH   OH               H    H2213       4-iPrO-Ph      NH  F1              NH   OH               H    H2214       4-iPrO-Ph      NH  F2              NH   OH               H    H2215       4-iPrO-Ph      NH  F3              NH   OH               H    H2216       4-iPrO-Ph      NH  F4              NH   OH               H    H2217       4-iPrO-Ph      NH  F5              NH   OH               H    H2218       4-iPrO-Ph      NH  F6              NH   OH               H    H2219       4-iPrO-Ph      NH  F7              NH   OH               H    H2220       4-iPrO-Ph      NH  F8              NH   OH               H    H2221       4-iPrO-Ph      NH  F9              NH   OH               H    H2222       4-iPrO-Ph      NH  F10             NH   OH               H    H2223       4-iPrO-Ph      NH  Ph              NH   OH               H    H2224       4-iPrO-Ph      NH  Bn              NH   OH               H    H2225       4-iPrO-Ph      NH  Pe              NH   OH               H    H2226       4-iPrO-Ph      NH  C12             NMe  OH               H    H2227       4-iPrO-Ph      NH  C12             NEt  OH               H    H2228       4-iPrO-Ph      NH  C12             NPr  OH               H    H2229       4-iPrO-Ph      NH  (CH2)3       N    OH               H    H2230       4-iPrO-Ph      NH  (CH2)4       N    OH               H    H2231       4-iPrO-Ph      NH  (CH2)5       N    OH               H    H2232       4-iPrO-Ph      NH  C12             O    OH               H    H2233       4-iPrO-Ph      NH  Ph              O    OH               H    H2234       4-iPrO-Ph      NH  C12             S    OH               H    H2235       4-iPrO-Ph      NH  Ph              S    OH               H    H2236   4-iPrO-Ph               NMe     H           NH      OH           H        H2237   4-iPrO-Ph               NEt     H           NH      OH           H        H2238   4-iPrO-Ph               NPr     H           NH      OH           H        H2239   4-iPrO-Ph               O       H           NH      OH           H        H2240   4-iPrO-Ph               S       H           NH      OH           H        H2241   4-BuO-Ph                NH      H           NH      H            H        H2242   4-BuO-Ph                NH      H           NH      OH           H        H2243   4-BuO-Ph                NH      H           NH      OA6          H        H2244   4-BuO-Ph                NH      H           NH      OA8          H        H2245   4-BuO-Ph                NH      H           NH      OA9          H        H2246   4-BuO-Ph                NH      H           NH      OA10         H        H2247   4-BuO-Ph                NH      H           NH      OA12         H        H2248   4-BuO-Ph                NH      H           NH      OA14         H        H2249   4-BuO-Ph                NH      H           NH      OA16         H        H2250   4-BuO-Ph                NH      H           NH      OH           H        A62251   4-BuO-Ph                NH      H           NH      OH           H        A82252   4-BuO-Ph                NH      H           NH      OH           H        A92253   4-BuO-Ph                NH      H           NH      OH           H        A102254   4-BuO-Ph                NH      H           NH      OH           H        A122255   4-BuO-Ph                NH      H           NH      OH           H        A142256   4-BuO-Ph                NH      H           NH      OH           H        A162257   4-BuO-Ph                NH      H           NH      OH           A6       A62258   4-BuO-Ph                NH      H           NH      OH           A8       A82259   4-BuO-Ph                NH      H           NH      OH           A10      A102260   4-BuO-Ph                NH      H           NH      OA2          A2       A22261   4-BuO-Ph                NH      H           NH      OA3          A3       A32262   4-BuO-Ph                NH      H           NH      OA4          A4       A42263   4-BuO-Ph                NH      H           NH      OC6          H        H2264   4-BuO-Ph                NH      H           NH      OC7          H        H2265  4-BuO-Ph       NH  H           NH          OC8            H    H2266  4-BuO-Ph       NH  H           NH          OC10           H    H2267  4-BuO-Ph       NH  H           NH          OC11           H    H2268  4-BuO-Ph       NH  H           NH          OC12           H    H2269  4-BuO-Ph       NH  H           NH          OC14           H    H2270  4-BuO-Ph       NH  H           NH          OC16           H    H2271  4-BuO-Ph       NH  H           NH          C6CO3         H    H2272  4-BuO-Ph       NH  H           NH          C7CO3         H    H2273  4-BuO-Ph       NH  H           NH          C8CO3         H    H2274  4-BuO-Ph       NH  H           NH          C9CO3         H    H2275  4-BuO-Ph       NH  H           NH          C10CO3        H    H2276  4-BuO-Ph       NH  H           NH          C12CO3        H    H2277  4-BuO-Ph       NH  H           NH          C16CO3        H    H2278  4-BuO-Ph       NH  C8          NH          OH             H    H2279  4-BuO-Ph       NH  C9          NH          OH             H    H2280  4-BuO-Ph       NH  C10         NH          OH             H    H2281  4-BuO-Ph       NH  C12         NH          OH             H    H2282  4-BuO-Ph       NH  C16         NH          OH             H    H2283  4-BuO-Ph       NH  F1          NH          OH             H    H2284  4-BuO-Ph       NH  F2          NH          OH             H    H2285  4-BuO-Ph       NH  F3          NH          OH             H    H2286  4-BuO-Ph       NH  F4          NH          OH             H    H2287  4-BuO-Ph       NH  F5          NH          OH             H    H2288  4-BuO-Ph       NH  F6          NH          OH             H    H2289  4-BuO-Ph       NH  F7          NH          OH             H    H2290  4-BuO-Ph       NH  F8          NH          OH             H    H2291  4-BuO-Ph       NH  F9          NH          OH             H    H2292  4-BuO-Ph       NH  F10         NH          OH             H    H2293  4-BuO-Ph       NH  Ph          NH          OH             H    H2294       4-BuO-Ph       NH   Bn              NH   OH              H    H2295       4-BuO-Ph       NH   Pe              NH   OH              H    H2296       4-BuO-Ph       NH   C12             NMe  OH              H    H2297       4-BuO-Ph       NH   C12             NEt  OH              H    H2298       4-BuO-Ph       NH   C12             NPr  OH              H    H2299       4-BuO-Ph       NH   (CH2)3       N    OH              H    H2300       4-BuO-Ph       NH   (CH2)4       N    OH              H    H2301       4-BuO-Ph       NH   (CH2)5       N    OH              H    H2302       4-BuO-Ph       NH   C12             O    OH              H    H2303       4-BuO-Ph       NH   Ph              O    OH              H    H2304       4-BuO-Ph       NH   C12             S    OH              H    H2305       4-BuO-Ph       NH   Ph              S    OH              H    H2306       4-BuO-Ph       NMe  H               NH   OH              H    H2307       4-BuO-Ph       NEt  H               NH   OH              H    H2308       4-BuO-Ph       NPr  H               NH   OH              H    H2309       4-BuO-Ph       O    H               NH   OH              H    H2310       4-BuO-Ph       S    H               NH   OH              H    H2311       4-PenO-Ph      NH   H               NH   H               H    H2312       4-PenO-Ph      NH   H               NH   OH              H    H2313       4-PenO-Ph      NH   H               NH   OA6             H    H2314       4-PenO-Ph      NH   H               NH   OA8             H    H2315       4-PenO-Ph      NH   H               NH   OA9             H    H2316       4-PenO-Ph      NH   H               NH   OA10            H    H2317       4-PenO-Ph      NH   H               NH   OA12            H    H2318       4-PenO-Ph      NH   H               NH   OA14            H    H2319       4-PenO-Ph      NH   H               NH   OA16            H    H2320       4-PenO-Ph      NH   H               NH   OH              H    A62321       4-PenO-Ph      NH   H               NH   OH              H    A82322       4-PenO-Ph      NH   H               NH   OH              H    A92323       4-PenO-Ph      NH   H             NH   OH              H    A102324       4-PenO-Ph      NH   H             NH   OH              H    A122325       4-PenO-Ph      NH   H             NH   OH              H    A142326       4-PenO-Ph      NH   H             NH   OH              H    A162327       4-PenO-Ph      NH   H             NH   OH              A6   A62328       4-PenO-Ph      NH   H             NH   OH              A8   A82329       4-PenO-Ph      NH   H             NH   OH              A10  A102330       4-PenO-Ph      NH   H             NH   OA2             A2   A22331       4-PenO-Ph      NH   H             NH   OA3             A3   A32332       4-PenO-Ph      NH   H             NH   OA4             A4   A42333       4-PenO-Ph      NH   H             NH   OC6             H    H2334       4-PenO-Ph      NH   H             NH   OC7             H    H2335       4-PenO-Ph      NH   H             NH   OC8             H    H2336       4-PenO-Ph      NH   H             NH   OC10            H    H2337       4-PenO-Ph      NH   H             NH   OC1             H    H2338       4-PenO-Ph      NH   H             NH   OC12            H    H2339       4-PenO-Ph      NH   H             NH   OC14            H    H2340       4-PenO-Ph      NH   H             NH   OC16            H    H2341       4-PenO-Ph      NH   H             NH   C6CO3          H    H2342       4-PenO-Ph      NH   H             NH   C7CO3          H    H2343       4-PenO-Ph      NH   H             NH   C8CO3          H    H2344       4-PenO-Ph      NH   H             NH   C9CO3          H    H2345       4-PenO-Ph      NH   H             NH   C10CO3         H    H2346       4-PenO-Ph      NH   H             NH   C12CO3         H    H2347       4-PenO-Ph      NH   H             NH   C16CO3         H    H2348       4-PenO-Ph      NH   C8            NH   OH              H    H2349       4-PenO-Ph      NH   C9            NH   OH              H    H2350       4-PenO-Ph      NH   C10           NH   OH              H    H2351       4-PenO-Ph      NH   C12           NH   OH              H    H2352       4-PenO-Ph       NH   C16               NH   OH           H    H2353       4-PenO-Ph       NH   F1                NH   OH           H    H2354       4-PenO-Ph       NH   F2                NH   OH           H    H2355       4-PenO-Ph       NH   F3                NH   OH           H    H2356       4-PenO-Ph       NH   F4                NH   OH           H    H2357       4-PenO-Ph       NH   F5                NH   OH           H    H2358       4-PenO-Ph       NH   F6                NH   OH           H    H2359       4-PenO-Ph       NH   F7                NH   OH           H    H2360       4-PenO-Ph       NH   F8                NH   OH           H    H2361       4-PenO-Ph       NH   F9                NH   OH           H    H2362       4-PenO-Ph       NH   F10               NH   OH           H    H2363       4-PenO-Ph       NH   Ph                NH   OH           H    H2364       4-PenO-Ph       NH   Bn                NH   OH           H    H2365       4-PenO-Ph       NH   Pe                NH   OH           H    H2366       4-PenO-Ph       NH   C12               NMe  OH           H    H2367       4-PenO-Ph       NH   C12               NEt  OH           H    H2368       4-PenO-Ph       NH   C12               NPr  OH           H    H2369       4-PenO-Ph       NH   (CH2)3         N    OH           H    H2370       4-PenO-Ph       NH   (CH2)4         N    OH           H    H2371       4-PenO-Ph       NH   (CH2)5         N    OH           H    H2372       4-PenO-Ph       NH   C12               O    OH           H    H2373       4-PenO-Ph       NH   Ph                O    OH           H    H2374       4-PenO-Ph       NH   C12               S    OH           H    H2375       4-PenO-Ph       NH   Ph                S    OH           H    H2376       4-PenO-Ph       NMe  H                 NH   OH           H    H2377       4-PenO-Ph       NEt  H                 NH   OH           H    H2378       4-PenO-Ph       NPr  H                 NH   OH           H    H2379       4-PenO-Ph       O    H                 NH   OH           H    H2380       4-PenO-Ph       S    H                 NH   OH           H    H2381  4-HexO-Ph      NH  H             NH   H               H             H2382  4-HexO-Ph      NH  H             NH   OH              H             H2383  4-HexO-Ph      NH  H             NH   OA6             H             H2384  4-HexO-Ph      NH  H             NH   OA8             H             H2385  4-HexO-Ph      NH  H             NH   OA9             H             H2386  4-HexO-Ph      NH  H             NH   OA10            H             H2387  4-HexO-Ph      NH  H             NH   OA12            H             H2388  4-HexO-Ph      NH  H             NH   OA14            H             H2389  4-HexO-Ph      NH  H             NH   OA16            H             H2390  4-HexO-Ph      NH  H             NH   OH              H             A62391  4-HexO-Ph      NH  H             NH   OH              H             A82392  4-HexO-Ph      NH  H             NH   OH              H             A92393  4-HexO-Ph      NH  H             NH   OH              H             A102394  4-HexO-Ph      NH  H             NH   OH              H             A122395  4-HexO-Ph      NH  H             NH   OH              H             A142396  4-HexO-Ph      NH  H             NH   OH              H             A162397  4-HexO-Ph      NH  H             NH   OH              A6            A62398  4-HexO-Ph      NH  H             NH   OH              A8            A82399  4-HexO-Ph      NH  H             NH   OH              A10           A102400  4-HexO-Ph      NH  H             NH   OA2             A2            A22401  4-HexO-Ph      NH  H             NH   OA3             A3            A32402  4-HexO-Ph      NH  H             NH   OA4             A4            A42403  4-HexO-Ph      NH  H             NH   OC6             H             H2404  4-HexO-Ph      NH  H             NH   OC7             H             H2405  4-HexO-Ph      NH  H             NH   OC8             H             H2406  4-HexO-Ph      NH  H             NH   OC10            H             H2407  4-HexO-Ph      NH  H             NH   OC11            H             H2408  4-HexO-Ph      NH  H             NH   OC12            H             H2409  4-HexO-Ph      NH  H             NH   OC14            H             H2410       4-HexO-Ph      NH   H                NH   OC16               H   H2411       4-HexO-Ph      NH   H                NH   C6CO3             H   H2412       4-HexO-Ph      NH   H                NH   C7CO3             H   H2413       4-HexO-Ph      NH   H                NH   C8CO3             H   H2414       4-HexO-Ph      NH   H                NH   C9CO3             H   H2415       4-HexO-Ph      NH   H                NH   C10CO3            H   H2416       4-HexO-Ph      NH   H                NH   C12CO3            H   H2417       4-HexO-Ph      NH   H                NH   C16CO3            H   H2418       4-HexO-Ph      NH   C8               NH   OH                 H   H2419       4-HexO-Ph      NH   C9               NH   OH                 H   H2420       4-HexO-Ph      NH   C10              NH   OH                 H   H2421       4-HexO-Ph      NH   C12              NH   OH                 H   H2422       4-HexO-Ph      NH   C16              NH   OH                 H   H2423       4-HexO-Ph      NH   F1               NH   OH                 H   H2424       4-HexO-Ph      NH   F2               NH   OH                 H   H2425       4-HexO-Ph      NH   F3               NH   OH                 H   H2426       4-HexO-Ph      NH   F4               NH   OH                 H   H2427       4-HexO-Ph      NH   F5               NH   OH                 H   H2428       4-HexO-Ph      NH   F6               NH   OH                 H   H2429       4-HexO-Ph      NH   F7               NH   OH                 H   H2430       4-HexO-Ph      NH   F8               NH   OH                 H   H2431       4-HexO-Ph      NH   F9               NH   OH                 H   H2432       4-HexO-Ph      NH   F10              NH   OH                 H   H2433       4-HexO-Ph      NH   Ph               NH   OH                 H   H2434       4-HexO-Ph      NH   Bn               NH   OH                 H   H2435       4-HexO-Ph      NH   Pe               NH   OH                 H   H2436       4-HexO-Ph      NH   C12              NMe  OH                 H   H2437       4-HexO-Ph      NH   C12              NEt  OH                 H   H2438       4-HexO-Ph      NH   C12              NPr  OH                 H   H2439       4-HexO-Ph       NH   (CH2)3       N    OH              H    H2440       4-HexO-Ph       NH   (CH2)4       N    OH              H    H2441       4-HexO-Ph       NH   (CH2)5       N    OH              H    H2442       4-HexO-Ph       NH   C12             O    OH              H    H2443       4-HexO-Ph       NH   Ph              O    OH              H    H2444       4-HexO-Ph       NH   C12             S    OH              H    H2445       4-HexO-Ph       NH   Ph              S    OH              H    H2446       4-HexO-Ph       NMe  H               NH   OH              H    H2447       4-HexO-Ph       NEt  H               NH   OH              H    H2448       4-HexO-Ph       NPr  H               NH   OH              H    H2449       4-HexO-Ph       O    H               NH   OH              H    H2450       4-HexO-Ph       S    H               NH   OH              H    H2451       3-BnO-Ph        NH   H               NH   H               H    H2452       3-BnO-Ph        NH   H               NH   OH              H    H2453       3-BnO-Ph        NH   H               NH   OA6             H    H2454       3-BnO-Ph        NH   H               NH   OA8             H    H2455       3-BnO-Ph        NH   H               NH   OA9             H    H2456       3-BnO-Ph        NH   H               NH   OA10            H    H2457       3-BnO-Ph        NH   H               NH   OA12            H    H2458       3-BnO-Ph        NH   H               NH   OA14            H    H2459       3-BnO-Ph        NH   H               NH   OA16            H    H2460       3-BnO-Ph        NH   H               NH   OH              H    A62461       3-BnO-Ph        NH   H               NH   OH              H    A82462       3-BnO-Ph        NH   H               NH   OH              H    A92463       3-BnO-Ph        NH   H               NH   OH              H    A102464       3-BnO-Ph        NH   H               NH   OH              H    A122465       3-BnO-Ph        NH   H               NH   OH              H    A142466       3-BnO-Ph        NH   H               NH   OH              H    A162467       3-BnO-Ph        NH   H               NH   OH              A6   A62468    3-BnO-Ph       NH   H             NH          OH             A8   A82469    3-BnO-Ph       NH   H             NH          OH             A10  A102470    3-BnO-Ph       NH   H             NH          OA2            A2   A22471    3-BnO-Ph       NH   H             NH          OA3            A3   A32472    3-BnO-Ph       NH   H             NH          OA4            A4   A42473    3-BnO-Ph       NH   H             NH          OC6            H    H2474    3-BnO-Ph       NH   H             NH          OC7            H    H2475    3-BnO-Ph       NH   H             NH          OC8            H    H2476    3-BnO-Ph       NH   H             NH          OC10           H    H2477    3-BnO-Ph       NH   H             NH          OC11           H    H2478    3-BnO-Ph       NH   H             NH          OC12           H    H2479    3-BnO-Ph       NH   H             NH          OC14           H    H2480    3-BnO-Ph       NH   H             NH          OC16           H    H2481    3-BnO-Ph       NH   H             NH          C6CO3         H    H2482    3-BnO-Ph       NH   H             NH          C7CO3         H    H2483    3-BnO-Ph       NH   H             NH          C8CO3         H    H2484    3-BnO-Ph       NH   H             NH          C9CO3         H    H2485    3-BnO-Ph       NH   H             NH          C10CO3        H    H2486    3-BnO-Ph       NH   H             NH          C12CO3        H    H2487    3-BnO-Ph       NH   H             NH          C16CO3        H    H2488    3-BnO-Ph       NH   C8            NH          OH             H    H2489    3-BnO-Ph       NH   C9            NH          OH             H    H2490    3-BnO-Ph       NH   C10           NH          OH             H    H2491    3-BnO-Ph       NH   C12           NH          OH             H    H2492    3-BnO-Ph       NH   C16           NH          OH             H    H2493    3-BnO-Ph       NH   F1            NH          OH             H    H2494    3-BnO-Ph       NH   F2            NH          OH             H    H2495    3-BnO-Ph       NH   F3            NH          OH             H    H2496    3-BnO-Ph       NH   F4            NH          OH             H    H2497    3-BnO-Ph              NH   F5            NH   OH            H   H2498    3-BnO-Ph              NH   F6            NH   OH            H   H2499    3-BnO-Ph              NH   F7            NH   OH            H   H2500    3-BnO-Ph              NH   F8            NH   OH            H   H2501    3-BnO-Ph              NH   F9            NH   OH            H   H2502    3-BnO-Ph              NH   F10           NH   OH            H   H2503    3-BnO-Ph              NH   Ph            NH   OH            H   H2504    3-BnO-Ph              NH   Bn            NH   OH            H   H2505    3-BnO-Ph              NH   Pe            NH   OH            H   H2506    3-BnO-Ph              NH   C12           NMe  OH            H   H2507    3-BnO-Ph              NH   C12           NEt  OH            H   H2508    3-BnO-Ph              NH   C12           NPr  OH            H   H2509    3-BnO-Ph              NH   (CH2)3     N    OH            H   H2510    3-BnO-Ph              NH   (CH2)4     N    OH            H   H2511    3-BnO-Ph              NH   (CH2)5     N    OH            H   H2512    3-BnO-Ph              NH   C12           O    OH            H   H2513    3-BnO-Ph              NH   Ph            O    OH            H   H2514    3-BnO-Ph              NH   C12           S    OH            H   H2515    3-BnO-Ph              NH   Ph            S    OH            H   H2516    3-BnO-Ph              NMe  H             NH   OH            H   H2517    3-BnO-Ph              NEt  H             NH   OH            H   H2518    3-BnO-Ph              NPr  H             NH   OH            H   H2519    3-BnO-Ph              O    H             NH   OH            H   H2520    3-BnO-Ph              S    H             NH   OH            H   H2521    2-Me-4-MeO-Ph         NH   H             NH   H             H   H2522    2-Me-4-MeO-Ph         NH   H             NH   OH            H   H2523    2-Me-4-MeO-Ph         NH   H             NH   OA6           H   H2524    2-Me-4-MeO-Ph         NH   H             NH   OA8           H   H2525    2-Me-4-MeO-Ph         NH   H             NH   OA9           H   H2526    2-Me-4-MeO-Ph    NH   H            NH   OA10                H    H2527    2-Me-4-MeO-Ph    NH   H            NH   OA12                H    H2528    2-Me-4-MeO-Ph    NH   H            NH   OA14                H    H2529    2-Me-4-MeO-Ph    NH   H            NH   OA16                H    H2530    2-Me-4-MeO-Ph    NH   H            NH   OH                  H    A62531    2-Me-4-MeO-Ph    NH   H            NH   OH                  H    A82532    2-Me-4-MeO-Ph    NH   H            NH   OH                  H    A92533    2-Me-4-MeO-Ph    NH   H            NH   OH                  H    A102534    2-Me-4-MeO-Ph    NH   H            NH   OH                  H    A122535    2-Me-4-MeO-Ph    NH   H            NH   OH                  H    A142536    2-Me-4-MeO-Ph    NH   H            NH   OH                  H    A162537    2-Me-4-MeO-Ph    NH   H            NH   OH                  A6   A62538    2-Me-4-MeO-Ph    NH   H            NH   OH                  A8   A82539    2-Me-4-MeO-Ph    NH   H            NH   OH                  A10  A102540    2-Me-4-MeO-Ph    NH   H            NH   OA2                 A2   A22541    2-Me-4-MeO-Ph    NH   H            NH   OA3                 A3   A32542    2-Me-4-MeO-Ph    NH   H            NH   OA4                 A4   A42543    2-Me-4-MeO-Ph    NH   H            NH   OC6                 H    H2544    2-Me-4-MeO-Ph    NH   H            NH   OC7                 H    H2545    2-Me-4-MeO-Ph    NH   H            NH   OC8                 H    H2546    2-Me-4-MeO-Ph    NH   H            NH   OC10                H    H2547    2-Me-4-MeO-Ph    NH   H            NH   OC11                H    H2548    2-Me-4-MeO-Ph    NH   H            NH   OC12                H    H2549    2-Me-4-MeO-Ph    NH   H            NH   OC14                H    H2550    2-Me-4-MeO-Ph    NH   H            NH   OC16                H    H2551    2-Me-4-MeO-Ph    NH   H            NH   C6CO3              H    H2552    2-Me-4-MeO-Ph    NH   H            NH   C7CO3              H    H2553    2-Me-4-MeO-Ph    NH   H            NH   C8CO3              H    H2554    2-Me-4-MeO-Ph    NH   H            NH   C9CO3              H    H2555      2-Me-4-MeO-Ph          NH   H            NH   C10CO3   H   H2556      2-Me-4-MeO-Ph          NH   H            NH   C12CO3   H   H2557      2-Me-4-MeO-Ph          NH   H            NH   C16CO3   H   H2558      2-Me-4-MeO-Ph          NH   C8           NH   OH        H   H2559      2-Me-4-MeO-Ph          NH   C9           NH   OH        H   H2560      2-Me-4-MeO-Ph          NH   C10          NH   OH        H   H2561      2-Me-4-MeO-Ph          NH   C12          NH   OH        H   H2562      2-Me-4-MeO-Ph          NH   C16          NH   OH        H   H2563      2-Me-4-MeO-Ph          NH   F1           NH   OH        H   H2564      2-Me-4-MeO-Ph          NH   F2           NH   OH        H   H2565      2-Me-4-MeO-Ph          NH   F3           NH   OH        H   H2566      2-Me-4-MeO-Ph          NH   F4           NH   OH        H   H2567      2-Me-4-MeO-Ph          NH   F5           NH   OH        H   H2568      2-Me-4-MeO-Ph          NH   F6           NH   OH        H   H2569      2-Me-4-MeO-Ph          NH   F7           NH   OH        H   H2570      2-Me-4-MeO-Ph          NH   F8           NH   OH        H   H2571      2-Me-4-MeO-Ph          NH   F9           NH   OH        H   H2572      2-Me-4-MeO-Ph          NH   F1O          NH   OH        H   H2573      2-Me-4-MeO-Ph          NH   Ph           NH   OH        H   H2574      2-Me-4-MeO-Ph          NH   Bn           NH   OH        H   H2575      2-Me-4-MeO-Ph          NH   Pe           NH   OH        H   H2576      2-Me-4-MeO-Ph          NH   C12          NMe  OH        H   H2577      2-Me-4-MeO-Ph          NH   C12          NEt  OH        H   H2578      2-Me-4-MeO-Ph          NH   C12          NPr  OH        H   H2579      2-Me-4-MeO-Ph          NH   (CH2)3    N    OH        H   H2580      2-Me-4-MeO-Ph          NH   (CH2)4    N    OH        H   H2581      2-Me-4-MeO-Ph          NH   (CH2)5    N    OH        H   H2582      2-Me-4-MeO-Ph          NH   C12          O    OH        H   H2583      2-Me-4-MeO-Ph          NH   Ph           O    OH        H   H2584      2-Me-4-MeO-Ph          NH   C12          S    OH             H    H2585      2-Me-4-MeO-Ph          NH   Ph           S    OH             H    H2586      2-Me-4-MeO-Ph          NMe  H            NH   OH             H    H2587      2-Me-4-MeO-Ph          NEt  H            NH   OH             H    H2588      2-Me-4-MeO-Ph          NPr  H            NH   OH             H    H2589      2-Me-4-MeO-Ph          O    H            NH   OH             H    H2590      2-Me-4-MeO-Ph          S    H            NH   OH             H    H2591      3-PhO-Ph               NH   H            NH   H              H    H2592      3-PhO-Ph               NH   H            NH   OH             H    H2593      3-PhO-Ph               NH   H            NH   OA6            H    H2594      3-PhO-Ph               NH   H            NH   OA8            H    H2595      3-PhO-Ph               NH   H            NH   OA9            H    H2596      3-PhO-Ph               NH   H            NH   OA10           H    H2597      3-PhO-Ph               NH   H            NH   OA12           H    H2598      3-PhO-Ph               NH   H            NH   OA14           H    H2599      3-PhO-Ph               NH   H            NH   OA16           H    H2600      3-PhO-Ph               NH   H            NH   OH             H    A62601      3-PhO-Ph               NH   H            NH   OH             H    A82602      3-PhO-Ph               NH   H            NH   OH             H    A92603      3-PhO-Ph               NH   H            NH   OH             H    A102604      3-PhO-Ph               NH   H            NH   OH             H    A122605      3-PhO-Ph               NH   H            NH   OH             H    A142606      3-PhO-Ph               NH   H            NH   OH             H    A162607      3-PhO-Ph               NH   H            NH   OH             A6   A62608      3-PhO-Ph               NH   H            NH   OH             A8   A82609      3-PhO-Ph               NH   H            NH   OH             A10  A102610      3-PhO-Ph               NH   H            NH   OA2            A2   A22611      3-PhO-Ph               NH   H            NH   OA3            A3   A32612      3-PhO-Ph               NH   H            NH   OA4            A4   A42613  3-PhO-Ph                 NH      H          NH       OC6           H       H2614  3-PhO-Ph                 NH      H          NH       OC7           H       H2615  3-PhO-Ph                 NH      H          NH       OC8           H       H2616  3-PhO-Ph                 NH      H          NH       OC10          H       H2617  3-PhO-Ph                 NH      H          NH       OC11          H       H2618  3-PhO-Ph                 NH      H          NH       OC12          H       H2619  3-PhO-Ph                 NH      H          NH       OC14          H       H2620  3-PhO-Ph                 NH      H          NH       OC16          H       H2621  3-PhO-Ph                 NH      H          NH       C6CO3        H       H2622  3-PhO-Ph                 NH      H          NH       C7CO3        H       H2623  3-PhO-Ph                 NH      H          NH       C8CO3        H       H2624  3-PhO-Ph                 NH      H          NH       C9CO3        H       H2625  3-PhO-Ph                 NH      H          NH       C10CO3       H       H2626  3-PhO-Ph                 NH      H          NH       C12CO3       H       H2627  3-PhO-Ph                 NH      H          NH       C16CO3       H       H2628  3-PhO-Ph                 NH      C8         NH       OH            H       H2629  3-PhO-Ph                 NH      C9         NH       OH            H       H2630  3-PhO-Ph                 NH      C10        NH       OH            H       H2631  3-PhO-Ph                 NH      C12        NH       OH            H       H2632  3-PhO-Ph                 NH      C16        NH       OH            H       H2633  3-PhO-Ph                 NH      F1         NH       OH            H       H2634  3-PhO-Ph                 NH      F2         NH       OH            H       H2635  3-PhO-Ph                 NH      F3         NH       OH            H       H2636  3-PhO-Ph                 NH      F4         NH       OH            H       H2637  3-PhO-Ph                 NH      F5         NH       OH            H       H2638  3-PhO-Ph                 NH      F6         NH       OH            H       H2639  3-PhO-Ph                 NH      F7         NH       OH            H       H2640  3-PhO-Ph                 NH      F8         NH       OH            H       H2641  3-PhO-Ph                 NH      F9         NH       OH            H       H2642      3-PhO-Ph         NH   F10             NH     OH             H   H2643      3-PhO-Ph         NH   Ph              NH     OH             H   H2644      3-PhO-Ph         NH   Bn              NH     OH             H   H2645      3-PhO-Ph         NH   Pe              NH     OH             H   H2646      3-PhO-Ph         NH   C12             NMe    OH             H   H2647      3-PhO-Ph         NH   C12             NEt    OH             H   H2648      3-PhO-Ph         NH   C12             NPr    OH             H   H2649      3-PhO-Ph         NH   (CH2)3       N      OH             H   H2650      3-PhO-Ph         NH   (CH2)4       N      OH             H   H2651      3-PhO-Ph         NH   (CH2)5       N      OH             H   H2652      3-PhO-Ph         NH   C12             O      OH             H   H2653      3-PhO-Ph         NH   Ph              O      OH             H   H2654      3-PhO-Ph         NH   C12             S      OH             H   H2655      3-PhO-Ph         NH   Ph              S      OH             H   H2656      3-PhO-Ph         NMe  H               NH     OH             H   H2657      3-PhO-Ph         NEt  H               NH     OH             H   H2658      3-PhO-Ph         NPr  H               NH     OH             H   H2659      3-PhO-Ph         O    H               NH     OH             H   H2660      3-PhO-Ph         S    H               NH     OH             H   H2661      3,4-(OCH2O)-Ph NH   H               NH     H              H   H2662      3,4-(OCH2O)-Ph NH   H               NH     OH             H   H2663      3,4-(OCH2O)-Ph NH   H               NH     OA6            H   H2664      3,4-(OCH2O)-Ph NH   H               NH     OA8            H   H2665      3,4-(OCH2O)-Ph NH   H               NH     OA9            H   H2666      3,4-(OCH2O)-Ph NH   H               NH     OA10           H   H2667      3,4-(OCH2O)-Ph NH   H               NH     OA12           H   H2668      3,4-(OCH2O)-Ph NH   H               NH     OA14           H   H2669      3,4-(OCH2O)-Ph NH   H               NH     OA16           H   H2670      3,4-(OCH2O)-Ph NH   H               NH     OH             H   A62671      3,4-(OCH2O)-Ph          NH  H            NH  OH             H   A82672      3,4-(OCH2O)-Ph          NH  H            NH  OH             H   A92673      3,4-(OCH2O)-Ph          NH  H            NH  OH             H   A102674      3,4-(OCH2O)-Ph          NH  H            NH  OH             H   A122675      3,4-(OCH2O)-Ph          NH  H            NH  OH             H   A142676      3,4-(OCH2O)-Ph          NH  H            NH  OH             H   A162677      3,4-(OCH2O)-Ph          NH  H            NH  OH             A6  A62678      3,4-(OCH2O)-Ph          NH  H            NH  OH             A8  A82679      3,4-(OCH2O)-Ph          NH  H            NH  OH             A10 A102680      3,4-(OCH2O)-Ph          NH  H            NH  OA2            A2  A22681      3,4-(OCH2O)-Ph          NH  H            NH  OA3            A3  A32682      3,4-(OCH2O)-Ph          NH  H            NH  OA4            A4  A42683      3,4-(OCH2O)-Ph          NH  H            NH  OC6            H   H2684      3,4-(OCH2O)-Ph          NH  H            NH  OC7            H   H2685      3,4-(OCH2O)-Ph          NH  H            NH  OC8            H   H2686      3,4-(OCH2O)-Ph          NH  H            NH  OC10           H   H2687      3,4-(OCH2O)-Ph          NH  H            NH  OC11           H   H2688      3,4-(OCH2O)-Ph          NH  H            NH  OC12           H   H2689      3,4-(OCH2O)-Ph          NH  H            NH  OC14           H   H2690      3,4-(OCH2O)-Ph          NH  H            NH  OC16           H   H2691      3,4-(OCH2O)-Ph          NH  H            NH  C6CO3         H   H2692      3,4-(OCH2O)-Ph          NH  H            NH  C7CO3         H   H2693      3,4-(OCH2O)-Ph          NH  H            NH  C8CO3         H   H2694      3,4-(OCH2O)-Ph          NH  H            NH  C9CO3         H   H2695      3,4-(OCH2O)-Ph          NH  H            NH  C10CO3        H   H2696      3,4-(OCH2O)-Ph          NH  H            NH  C12CO3        H   H2697      3,4-(OCH2O)-Ph          NH  H            NH  C16CO3        H   H2698      3,4-(OCH2O)-Ph          NH  C8           NH  OH             H   H2699      3,4-(OCH2O)-Ph          NH  C9           NH  OH             H   H2700   3,4-(OCH2O)-Ph           NH           C10            NH   OH    H   H2701   3,4-(OCH2O)-Ph           NH           C12            NH   OH    H   H2702   3,4-(OCH2O)-Ph           NH           C16            NH   OH    H   H2703   3,4-(OCH2O)-Ph           NH           F1             NH   OH    H   H2704   3,4-(OCH2O)-Ph           NH           F2             NH   OH    H   H2705   3,4-(OCH2O)-Ph           NH           F3             NH   OH    H   H2706   3,4-(OCH2O)-Ph           NH           F4             NH   OH    H   H2707   3,4-(OCH2O)-Ph           NH           F5             NH   OH    H   H2708   3,4-(OCH2O)-Ph           NH           F6             NH   OH    H   H2709   3,4-(OCH2O)-Ph           NH           F7             NH   OH    H   H2710   3,4-(OCH2O)-Ph           NH           F8             NH   OH    H   H2711   3,4-(OCH2O)-Ph           NH           F9             NH   OH    H   H2712   3,4-(OCH2O)-Ph           NH           F1O            NH   OH    H   H2713   3,4-(OCH2O)-Ph           NH           Ph             NH   OH    H   H2714   3,4-(OCH2O)-Ph           NH           Bn             NH   OH    H   H2715   3,4-(OCH2O)-Ph           NH           Pe             NH   OH    H   H2716   3,4-(OCH2O)-Ph           NH           C12            NMe  OH    H   H2717   3,4-(OCH2O)-Ph           NH           C12            NEt  OH    H   H2718   3,4-(OCH2O)-Ph           NH           C12            NPr  OH    H   H2719   3,4-(OCH2O)-Ph           NH           (CH2)3      N    OH    H   H2720   3,4-(OCH2O)-Ph           NH           (CH2)4      N    OH    H   H2721   3,4-(OCH2O)-Ph           NH           (CH2)5      N    OH    H   H2722   3,4-(OCH2O)-Ph           NH           C12            O    OH    H   H2723   3,4-(OCH2O)-Ph           NH           Ph             O    OH    H   H2724   3,4-(OCH2O)-Ph           NH           C12            S    OH    H   H2725   3,4-(OCH2O)-Ph           NH           Ph             S    OH    H   H2726   3,4-(OCH2O)-Ph           NMe          H              NH   OH    H   H2727   3,4-(OCH2O)-Ph           NEt          H              NH   OH    H   H2728   3,4-(OCH2O)-Ph           NPr          H              NH   OH    H   H2729     3,4-(OCH2O)-Ph          O   H    NH          OH             H   H2730     3,4-(OCH2O)-Ph          S   H    NH          OH             H   H2731     3,5-(MeO)2-Ph           NH  H    NH          H              H   H2732     3,5-(MeO)2-Ph           NH  H    NH          OH             H   H2733     3,5-(MeO)2-Ph           NH  H    NH          OA6            H   H2734     3,5-(MeO)2-Ph           NH  H    NH          OA8            H   H2735     3,5-(MeO)2-Ph           NH  H    NH          OA9            H   H2736     3,5-(MeO)2-Ph           NH  H    NH          OA1O           H   H2737     3,5-(MeO)2-Ph           NH  H    NH          OA12           H   H2738     3,5-(MeO)2-Ph           NH  H    NH          OA14           H   H2739     3,5-(MeO)2-Ph           NH  H    NH          OA16           H   H2740     3,5-(MeO)2-Ph           NH  H    NH          OH             H   A62741     3,5-(MeO)2-Ph           NH  H    NH          OH             H   A82742     3,5-(MeO)2-Ph           NH  H    NH          OH             H   A92743     3,5-(MeO)2-Ph           NH  H    NH          OH             H   A102744     3,5-(MeO)2-Ph           NH  H    NH          OH             H   A122745     3,5-(MeO)2-Ph           NH  H    NH          OH             H   A142746     3,5-(MeO)2-Ph           NH  H    NH          OH             H   A162747     3,5-(MeO)2-Ph           NH  H    NH          OH             A6  A62748     3,5-(MeO)2-Ph           NH  H    NH          OH             A8  A82749     3,5-(MeO)2-Ph           NH  H    NH          OH             A10 A102750     3,5-(MeO)2-Ph           NH  H    NH          OA2            A2  A22751     3,5-(MeO)2-Ph           NH  H    NH          OA3            A3  A32752     3,5-(MeO)2-Ph           NH  H    NH          OA4            A4  A42753     3,5-(MeO)2-Ph           NH  H    NH          OC6            H   H2754     3,5-(MeO)2-Ph           NH  H    NH          OC7            H   H2755     3,5-(MeO)2-Ph           NH  H    NH          OC8            H   H2756     3,5-(MeO)2-Ph           NH  H    NH          OC10           H   H2757     3,5-(MeO)2-Ph           NH  H    NH          OC11           H   H2758     3,5-(MeO)2-Ph        NH      H         NH      OC12          H   H2759     3,5-(MeO)2-Ph        NH      H         NH      OC14          H   H2760     3,5-(MeO)2-Ph        NH      H         NH      OC16          H   H2761     3,5-(MeO)2-Ph        NH      H         NH      C6CO3        H   H2762     3,5-(MeO)2-Ph        NH      H         NH      C7CO3        H   H2763     3,5-(MeO)2-Ph        NH      H         NH      C8CO3        H   H2764     3,5-(MeO)2-Ph        NH      H         NH      C9CO3        H   H2765     3,5-(MeO)2-Ph        NH      H         NH      C10CO3       H   H2766     3,5-(MeO)2-Ph        NH      H         NH      C12CO3       H   H2767     3,5-(MeO)2-Ph        NH      H         NH      C16CO3       H   H2768     3,5-(MeO)2-Ph        NH      C8        NH      OH            H   H2769     3,5-(MeO)2-Ph        NH      C9        NH      OH            H   H2770     3,5-(MeO)2-Ph        NH      C10       NH      OH            H   H2771     3,5-(MeO)2-Ph        NH      C12       NH      OH            H   H2772     3,5-(MeO)2-Ph        NH      C16       NH      OH            H   H2773     3,5-(MeO)2-Ph        NH      F1        NH      OH            H   H2774     3,5-(MeO)2-Ph        NH      F2        NH      OH            H   H2775     3,5-(MeO)2-Ph        NH      F3        NH      OH            H   H2776     3,5-(MeO)2-Ph        NH      F4        NH      OH            H   H2777     3,5-(MeO)2-Ph        NH      F5        NH      OH            H   H2778     3,5-(MeO)2-Ph        NH      F6        NH      OH            H   H2779     3,5-(MeO)2-Ph        NH      F7        NH      OH            H   H2780     3,5-(MeO)2-Ph        NH      F8        NH      OH            H   H2781     3,5-(MeO)2-Ph        NH      F9        NH      OH            H   H2782     3,5-(MeO)2-Ph        NH      F10       NH      OH            H   H2783     3,5-(MeO)2-Ph        NH      Ph        NH      OH            H   H2784     3,5-(MeO)2-Ph        NH      Bn        NH      OH            H   H2785     3,5-(MeO)2-Ph        NH      Pe        NH      OH            H   H2786     3,5-(MeO)2-Ph        NH      C12       NMe     OH            H   H2787  3,5-(MeO)2-Ph        NH      C12          NEt     OH            H        H2788  3,5-(MeO)2-Ph        NH      C12          NPr     OH            H        H2789  3,5-(MeO)2-Ph        NH      (CH2)3    N       OH            H        H2790  3,5-(MeO)2-Ph        NH      (CH2)4    N       OH            H        H2791  3,5-(MeO)2-Ph        NH      (CH2)5    N       OH            H        H2792  3,5-(MeO)2-Ph        NH      C12          O       OH            H        H2793  3,5-(MeO)2-Ph        NH      Ph           O       OH            H        H2794  3,5-(MeO)2-Ph        NH      C12          S       OH            H        H2795  3,5-(MeO)2-Ph        NH      Ph           S       OH            H        H2796  3,5-(MeO)2-Ph        NMe     H            NH      OH            H        H2797  3,5-(MeO)2-Ph        HEt     H            NH      OH            H        H2798  3,5-(MeO)2-Ph        NPr     H            NH      OH            H        H2799  3,5-(MeO)2-Ph        O       H            NH      OH            H        H2800  3,5-(MeO)2-Ph        S       H            NH      OH            H        H2801  3,4,5-(MeO)3-Ph     NH      H            NH      H             H        H2802  3,4,5-(MeO)3-Ph     NH      H            NH      OH            H        H2803  3,4,5-(MeO)3-Ph     NH      H            NH      OA6           H        H2804  3,4,5-(MeO)3-Ph     NH      H            NH      OA8           H        H2805  3,4,5-(MeO)3-Ph     NH      H            NH      OA9           H        H2806  3,4,5-(MeO)3-Ph     NH      H            NH      OA10          H        H2807  3,4,5-(MeO)3-Ph     NH      H            NH      OA12          H        H2808  3,4,5-(MeO)3-Ph     NH      H            NH      OA14          H        H2809  3,4,5-(MeO)3-Ph     NH      H            NH      OA16          H        H2810  3,4,5-(MeO)3-Ph     NH      H            NH      OH            H        A62811  3,4,5-(MeO)3-Ph     NH      H            NH      OH            H        A82812  3,4,5-(MeO)3-Ph     NH      H            NH      OH            H        A92813  3,4,5-(MeO)3-Ph     NH      H            NH      OH            H        A102814  3,4,5-(MeO)3-Ph     NH      H            NH      OH            H        A122815  3,4,5-(MeO)3-Ph     NH      H            NH      OH            H        A142816  3,4,5-(MeO)3-Ph        NH   H           NH  OH                H    A162817  3,4,5-(MeO)3-Ph        NH   H           NH  OH                A6   A62818  3,4,5-(MeO)3-Ph        NH   H           NH  OH                A8   A82819  3,4,5-(MeO)3-Ph        NH   H           NH  OH                A10  A102820  3,4,5-(MeO)3-Ph        NH   H           NH  OA2               A2   A22821  3,4,5-(MeO)3-Ph        NH   H           NH  OA3               A3   A32822  3,4,5-(MeO)3-Ph        NH   H           NH  OA4               A4   A42823  3,4,5-(MeO)3-Ph        NH   H           NH  OC6               H    H2824  3,4,5-(MeO)3-Ph        NH   H           NH  OC7               H    H2825  3,4,5-(MeO)3-Ph        NH   H           NH  OC8               H    H2826  3,4,5-(MeO)3-Ph        NH   H           NH  OC10              H    H2827  3,4,5-(MeO)3-Ph        NH   H           NH  OC11              H    H2828  3,4,5-(MeO)3-Ph        NH   H           NH  OC12              H    H2829  3,4,5-(MeO)3-Ph        NH   H           NH  OC14              H    H2830  3,4,5-(MeO)3-Ph        NH   H           NH  OC16              H    H2831  3,4,5-(MeO)3-Ph        NH   H           NH  C6CO3            H    H2832  3,4,5-(MeO)3-Ph        NH   H           NH  C7CO3            H    H2833  3,4,5-(MeO)3-Ph        NH   H           NH  C8CO3            H    H2834  3,4,5-(MeO)3-Ph        NH   H           NH  C9CO3            H    H2835  3,4,5-(MeO)3-Ph        NH   H           NH  C10CO3           H    H2836  3,4,5-(MeO)3-Ph        NH   H           NH  C12CO3           H    H2837  3,4,5-(MeO)3-Ph        NH   H           NH  C16CO3           H    H2838  3,4,5-(MeO)3-Ph        NH   C8          NH  OH                H    H2839  3,4,5-(MeO)3-Ph        NH   C9          NH  OH                H    H2840  3,4,5-(MeO)3-Ph        NH   C10         NH  OH                H    H2841  3,4,5-(MeO)3-Ph        NH   C12         NH  OH                H    H2842  3,4,5-(MeO)3-Ph        NH   C16         NH  OH                H    H2843  3,4,5-(MeO)3-Ph        NH   F1          NH  OH                H    H2844  3,4,5-(MeO)3-Ph        NH   F2          NH  OH                H    H2845   3,4,5-(MeO)3-Ph        NH  F3           NH   OH           H   H2846   3,4,5-(MeO)3-Ph        NH  F4           NH   OH           H   H2847   3,4,5-(MeO)3-Ph        NH  F5           NH   OH           H   H2848   3,4,5-(MeO)3-Ph        NH  F6           NH   OH           H   H2849   3,4,5-(MeO)3-Ph        NH  F7           NH   OH           H   H2850   3,4,5-(MeO)3-Ph        NH  F8           NH   OH           H   H2851   3,4,5-(MeO)3-Ph        NH  F9           NH   OH           H   H2852   3,4,5-(MeO)3-Ph        NH  F10          NH   OH           H   H2853   3,4,5-(MeO)3-Ph        NH  Ph           NH   OH           H   H2854   3,4,5-(MeO)3-Ph        NH  Bn           NH   OH           H   H2855   3,4,5-(MeO)3-Ph        NH  Pe           NH   OH           H   H2856   3,4,5-(MeO)3-Ph        NH  C12          NMe  OH           H   H2857   3,4,5-(MeO)3-Ph        NH  C12          NEt  OH           H   H2858   3,4,5-(MeO)3-Ph        NH  C12          NPr  OH           H   H2859   3,4,5-(MeO)3-Ph        NH  (CH2)3    N    OH           H   H2860   3,4,5-(MeO)3-Ph        NH  (CH2)4    N    OH           H   H2861   3,4,5-(MeO)3-Ph        NH  (CH2)5    N    OH           H   H2862   3,4,5-(MeO)3-Ph        NH  C12          O    OH           H   H2863   3,4,5-(MeO)3-Ph        NH  Ph           O    OH           H   H2864   3,4,5-(MeO)3-Ph        NH  C12          S    OH           H   H2865   3,4,5-(MeO)3-Ph        NH  Ph           S    OH           H   H2866   3,4,5-(MeO)3-Ph        NMe H            NH   OH           H   H2867   3,4,5-(MeO)3-Ph        NEt H            NH   OH           H   H2868   3,4,5-(MeO)3-Ph        NPr H            NH   OH           H   H2869   3,4,5-(MeO)3-Ph        O   H            NH   OH           H   H2870   3,4,5-(MeO)3-Ph        S   H            NH   OH           H   H2871   2-F-Ph                    NH  H            NH   H            H   H2872   2-F-Ph                    NH  H            NH   OH           H   H2873   2-F-Ph                    NH  H            NH   OA6          H   H2874   2-F-Ph                    NH       H             NH       OA8          H        H2875   2-F-Ph                    NH       H             NH       OA9          H        H2876   2-F-Ph                    NH       H             NH       OA10         H        H2877   2-F-Ph                    NH       H             NH       OA12         H        H2878   2-F-Ph                    NH       H             NH       OA14         H        H2879   2-F-Ph                    NH       H             NH       OA16         H        H2880   2-F-Ph                    NH       H             NH       OH           H        A62881   2-F-Ph                    NH       H             NH       OH           H        A82882   2-F-Ph                    NH       H             NH       OH           H        A92883   2-F-Ph                    NH       H             NH       OH           H        A102884   2-F-Ph                    NH       H             NH       OH           H        A122885   2-F-Ph                    NH       H             NH       OH           H        A142886   2-F-Ph                    NH       H             NH       OH           H        A162887   2-F-Ph                    NH       H             NH       OH           A6       A62888   2-F-Ph                    NH       H             NH       OH           A8       A82889   2-F-Ph                    NH       H             NH       OH           A10      A102890   2-F-Ph                    NH       H             NH       OA2          A2       A22891   2-F-Ph                    NH       H             NH       OA3          A3       A32892   2-F-Ph                    NH       H             NH       OA4          A4       A42893   2-F-Ph                    NH       H             NH       OC6          H        H2894   2-F-Ph                    NH       H             NH       OC7          H        H2895   2-F-Ph                    NH       H             NH       OC8          H        H2896   2-F-Ph                    NH       H             NH       OC10         H        H2897   2-F-Ph                    NH       H             NH       OC11         H        H2898   2-F-Ph                    NH       H             NH       OC12         H        H2899   2-F-Ph                    NH       H             NH       OC14         H        H2900   2-F-Ph                    NH       H             NH       OC16         H        H2901   2-F-Ph                    NH       H             NH       C6CO3       H        H2902   2-F-Ph                    NH       H             NH       C7CO3       H        H2903   2-F-Ph          NH   H                 NH   C8CO3             H    H2904   2-F-Ph          NH   H                 NH   C9CO3             H    H2905   2-F-Ph          NH   H                 NH   C10CO3            H    H2906   2-F-Ph          NH   H                 NH   C12CO3            H    H2907   2-F-Ph          NH   H                 NH   C16CO3            H    H2908   2-F-Ph          NH   C8                NH   OH                 H    H2909   2-F-Ph          NH   C9                NH   OH                 H    H2910   2-F-Ph          NH   C10               NH   OH                 H    H2911   2-F-Ph          NH   C12               NH   OH                 H    H2912   2-F-Ph          NH   C16               NH   OH                 H    H2913   2-F-Ph          NH   F1                NH   OH                 H    H2914   2-F-Ph          NH   F2                NH   OH                 H    H2915   2-F-Ph          NH   F3                NH   OH                 H    H2916   2-F-Ph          NH   F4                NH   OH                 H    H2917   2-F-Ph          NH   F5                NH   OH                 H    H2918   2-F-Ph          NH   F6                NH   OH                 H    H2919   2-F-Ph          NH   F7                NH   OH                 H    H2920   2-F-Ph          NH   F8                NH   OH                 H    H2921   2-F-Ph          NH   F9                NH   OH                 H    H2922   2-F-Ph          NH   F10               NH   OH                 H    H2923   2-F-Ph          NH   Ph                NH   OH                 H    H2924   2-F-Ph          NH   Bn                NH   OH                 H    H2925   2-F-Ph          NH   Pe                NH   OH                 H    H2926   2-F-Ph          NH   C12               NMe  OH                 H    H2927   2-F-Ph          NH   C12               NEt  OH                 H    H2928   2-F-Ph          NH   C12               NPr  OH                 H    H2929   2-F-Ph          NH   (CH2)3         N    OH                 H    H2930   2-F-Ph          NH   (CH2)4         N    OH                 H    H2931   2-F-Ph          NH   (CH2)5         N    OH                 H    H2932   2-F-Ph                      NH       C12           O        OH            H         H2933   2-F-Ph                      NH       Ph            O        OH            H         H2934   2-F-Ph                      NH       C12           S        OH            H         H2935   2-F-Ph                      NH       Ph            S        OH            H         H2936   2-F-Ph                      NMe      H             NH       OH            H         H2937   2-F-Ph                      NEt      H             NH       OH            H         H2938   2-F-Ph                      NPr      H             NH       OH            H         H2939   2-F-Ph                      O        H             NH       OH            H         H2940   2-F-Ph                      S        H             NH       OH            H         H2941   3-F-Ph                      NH       H             NH       H             H         H2942   3-F-Ph                      NH       H             NH       OH            H         H2943   3-F-Ph                      NH       H             NH       OA6           H         H2944   3-F-Ph                      NH       H             NH       OA8           H         H2945   3-F-Ph                      NH       H             NH       OA9           H         H2946   3-F-Ph                      NH       H             NH       OA10          H         H2947   3-F-Ph                      NH       H             NH       OA12          H         H2948   3-F-Ph                      NH       H             NH       OA14          H         H2949   3-F-Ph                      NH       H             NH       OA16          H         H2950   3-F-Ph                      NH       H             NH       OH            H         A62951   3-F-Ph                      NH       H             NH       OH            H         A82952   3-F-Ph                      NH       H             NH       OH            H         A92953   3-F-Ph                      NH       H             NH       OH            H         A102954   3-F-Ph                      NH       H             NH       OH            H         A122955   3-F-Ph                      NH       H             NH       OH            H         A142956   3-F-Ph                      NH       H             NH       OH            H         A162957   3-F-Ph                      NH       H             NH       OH            A6        A62958   3-F-Ph                      NH       H             NH       OH            A8        A82959   3-F-Ph                      NH       H             NH       OH            A10       A102960   3-F-Ph                      NH       H             NH       OA2           A2        A22961   3-F-Ph                     NH       H            NH      OA3          A3       A32962   3-F-Ph                     NH       H            NH      OA4          A4       A42963   3-F-Ph                     NH       H            NH      OC6          H        H2964   3-F-Ph                     NH       H            NH      OC7          H        H2965   3-F-Ph                     NH       H            NH      OC8          H        H2966   3-F-Ph                     NH       H            NH      OC10         H        H2967   3-F-Ph                     NH       H            NH      OC11         H        H2968   3-F-Ph                     NH       H            NH      OC12         H        H2969   3-F-Ph                     NH       H            NH      OC14         H        H2970   3-F-Ph                     NH       H            NH      OC16         H        H2971   3-F-Ph                     NH       H            NH      C6CO3       H        H2972   3-F-Ph                     NH       H            NH      C7CO3       H        H2973   3-F-Ph                     NH       H            NH      C8CO3       H        H2974   3-F-Ph                     NH       H            NH      C9CO3       H        H2975   3-F-Ph                     NH       H            NH      C10CO3      H        H2976   3-F-Ph                     NH       H            NH      C12CO3      H        H2977   3-F-Ph                     NH       H            NH      C16CO3      H        H2978   3-F-Ph                     NH       C8           NH      OH           H        H2979   3-F-Ph                     NH       C9           NH      OH           H        H2980   3-F-Ph                     NH       C10          NH      OH           H        H2981   3-F-Ph                     NH       C12          NH      OH           H        H2982   3-F-Ph                     NH       C16          NH      OH           H        H2983   3-F-Ph                     NH       F1           NH      OH           H        H2984   3-F-Ph                     NH       F2           NH      OH           H        H2985   3-F-Ph                     NH       F3           NH      OH           H        H2986   3-F-Ph                     NH       F4           NH      OH           H        H2987   3-F-Ph                     NH       F5           NH      OH           H        H2988   3-F-Ph                     NH       F6           NH      OH           H        H2989   3-F-Ph                     NH       F7           NH      OH           H        H2990   3-F-Ph         NH       F8          NH        OH            H         H2991   3-F-Ph         NH       F9          NH        OH            H         H2992   3-F-Ph         NH       F10         NH        OH            H         H2993   3-F-Ph         NH       Ph          NH        OH            H         H2994   3-F-Ph         NH       Bn          NH        OH            H         H2995   3-F-Ph         NH       Pe          NH        OH            H         H2996   3-F-Ph         NH       C12         NMe       OH            H         H2997   3-F-Ph         NH       C12         NEt       OH            H         H2998   3-F-Ph         NH       C12         NPr       OH            H         H2999   3-F-Ph         NH       (CH2)3   N         OH            H         H3000   3-F-Ph         NH       (CH2)4   N         OH            H         H3001   3-F-Ph         NH       (CH2)5   N         OH            H         H3002   3-F-Ph         NH       C12         O         OH            H         H3003   3-F-Ph         NH       Ph          O         OH            H         H3004   3-F-Ph         NH       C12         S         OH            H         H3005   3-F-Ph         NH       Ph          S         OH            H         H3006   3-F-Ph         NMe      H           NH        OH            H         H3007   3-F-Ph         NEt      H           NH        OH            H         H3008   3-F-Ph         NPr      H           NH        OH            H         H3009   3-F-Ph         O        H           NH        OH            H         H3010   3-F-Ph         S        H           NH        OH            H         H3011   4-F-Ph         NH       H           NH        H             H         H3012   4-F-Ph         NH       H           NH        OH            H         H3013   4-F-Ph         NH       H           NH        OA6           H         H3014   4-F-Ph         NH       H           NH        OA8           H         H3015   4-F-Ph         NH       H           NH        OA9           H         H3016   4-F-Ph         NH       H           NH        OA10          H         H3017   4-F-Ph         NH       H           NH        OA12          H         H3018   4-F-Ph         NH       H           NH        OA14          H         H3019   4-F-Ph                   NH      H           NH      OA16         H        H3020   4-F-Ph                   NH      H           NH      OH           H        A63021   4-F-Ph                   NH      H           NH      OH           H        A83022   4-F-Ph                   NH      H           NH      OH           H        A93023   4-F-Ph                   NH      H           NH      OH           H        A103024   4-F-Ph                   NH      H           NH      OH           H        A123025   4-F-Ph                   NH      H           NH      OH           H        A143026   4-F-Ph                   NH      H           NH      OH           H        A163027   4-F-Ph                   NH      H           NH      OH           A6       A63028   4-F-Ph                   NH      H           NH      OH           A8       A83029   4-F-Ph                   NH      H           NH      OH           A10      A103030   4-F-Ph                   NH      H           NH      OA2          A2       A23031   4-F-Ph                   NH      H           NH      OA3          A3       A33032   4-F-Ph                   NH      H           NH      OA4          A4       A43033   4-F-Ph                   NH      H           NH      OC6          H        H3034   4-F-Ph                   NH      H           NH      OC7          H        H3035   4-F-Ph                   NH      H           NH      OC8          H        H3036   4-F-Ph                   NH      H           NH      OC10         H        H3037   4-F-Ph                   NH      H           NH      OC11         H        H3038   4-F-Ph                   NH      H           NH      OC12         H        H3039   4-F-Ph                   NH      H           NH      OC14         H        H3040   4-F-Ph                   NH      H           NH      OC16         H        H3041   4-F-Ph                   NH      H           NH      C6CO3       H        H3042   4-F-Ph                   NH      H           NH      C7CO3       H        H3043   4-F-Ph                   NH      H           NH      C8CO3       H        H3044   4-F-Ph                   NH      H           NH      C9CO3       H        H3045   4-F-Ph                   NH      H           NH      C10CO3      H        H3046   4-F-Ph                   NH      H           NH      C12CO3      H        H3047   4-F-Ph                   NH      H           NH      C16CO3      H        H3048     4-F-Ph        NH      C8         NH      OH           H        H3049     4-F-Ph        NH      C9         NH      OH           H        H3050     4-F-Ph        NH      C10        NH      OH           H        H3051     4-F-Ph        NH      C12        NH      OH           H        H3052     4-F-Ph        NH      C16        NH      OH           H        H3053     4-F-Ph        NH      F1         NH      OH           H        H3054     4-F-Ph        NH      F2         NH      OH           H        H3055     4-F-Ph        NH      F3         NH      OH           H        H3056     4-F-Ph        NH      F4         NH      OH           H        H3057     4-F-Ph        NH      F5         NH      OH           H        H3058     4-F-Ph        NH      F6         NH      OH           H        H3059     4-F-Ph        NH      F7         NH      OH           H        H3060     4-F-Ph        NH      F8         NH      OH           H        H3061     4-F-Ph        NH      F9         NH      OH           H        H3062     4-F-Ph        NH      F10        NH      OH           H        H3063     4-F-Ph        NH      Ph         NH      OH           H        H3064     4-F-Ph        NH      Bn         NH      OH           H        H3065     4-F-Ph        NH      Pe         NH      OH           H        H3066     4-F-Ph        NH      C12        NMe     OH           H        H3067     4-F-Ph        NH      C12        NEt     OH           H        H3068     4-F-Ph        NH      C12        NPr     OH           H        H3069     4-F-Ph        NH      (CH2)3  N       OH           H        H3070     4-F-Ph        NH      (CH2)4  N       OH           H        H3071     4-F-Ph        NH      (CH2)5  N       OH           H        H3072     4-F-Ph        NH      C12        O       OH           H        H3073     4-F-Ph        NH      Ph         O       OH           H        H3074     4-F-Ph        NH      C12        S       OH           H        H3075     4-F-Ph        NH      Ph         S       OH           H        H3076     4-F-Ph        NMe     H          NH      OH           H        H3077   4-F-Ph                   NEt      H           NH       OH            H         H3078   4-F-Ph                   NPr      H           NH       OH            H         H3079   4-F-Ph                   O        H           NH       OH            H         H3080   4-F-Ph                   S        H           NH       OH            H         H3081   4-Cl-Ph                  NH       H           NH       H             H         H3082   4-Cl-Ph                  NH       H           NH       OH            H         H3083   4-Cl-Ph                  NH       H           NH       OA6           H         H3084   4-Cl-Ph                  NH       H           NH       OA8           H         H3085   4-Cl-Ph                  NH       H           NH       OA9           H         H3086   4-Cl-Ph                  NH       H           NH       OA10          H         H3087   4-Cl-Ph                  NH       H           NH       OA12          H         H3088   4-Cl-Ph                  NH       H           NH       OA14          H         H3089   4-Cl-Ph                  NH       H           NH       OA16          H         H3090   4-Cl-Ph                  NH       H           NH       OH            H         A63091   4-Cl-Ph                  NH       H           NH       OH            H         A83092   4-Cl-Ph                  NH       H           NH       OH            H         A93093   4-Cl-Ph                  NH       H           NH       OH            H         A103094   4-Cl-Ph                  NH       H           NH       OH            H         A123095   4-Cl-Ph                  NH       H           NH       OH            H         A143096   4-Cl-Ph                  NH       H           NH       OH            H         A163097   4-Cl-Ph                  NH       H           NH       OH            A6        A63098   4-Cl-Ph                  NH       H           NH       OH            A8        A83099   4-Cl-Ph                  NH       H           NH       OH            A10       A103100   4-Cl-Ph                  NH       H           NH       OA2           A2        A23101   4-Cl-Ph                  NH       H           NH       OA3           A3        A33102   4-Cl-Ph                  NH       H           NH       OA4           A4        A43103   4-Cl-Ph                  NH       H           NH       OC6           H         H3104   4-Cl-Ph                  NH       H           NH       OC7           H         H3105   4-Cl-Ph                  NH       H           NH       OC8           H         H3106     4-Cl-Ph          NH   H            NH   OC10           H        H3107     4-Cl-Ph          NH   H            NH   OC11           H        H3108     4-Cl-Ph          NH   H            NH   OC12           H        H3109     4-Cl-Ph          NH   H            NH   OC14           H        H3110     4-Cl-Ph          NH   H            NH   OC16           H        H3111     4-Cl-Ph          NH   H            NH   C6CO3         H        H3112     4-Cl-Ph          NH   H            NH   C7CO3         H        H3113     4-Cl-Ph          NH   H            NH   C8CO3         H        H3114     4-Cl-Ph          NH   H            NH   C9CO3         H        H3115     4-Cl-Ph          NH   H            NH   C10CO3        H        H3116     4-Cl-Ph          NH   H            NH   C12CO3        H        H3117     4-Cl-Ph          NH   H            NH   C16CO3        H        H3118     4-Cl-Ph          NH   C8           NH   OH             H        H3119     4-Cl-Ph          NH   C9           NH   OH             H        H3120     4-Cl-Ph          NH   C10          NH   OH             H        H3121     4-Cl-Ph          NH   C12          NH   OH             H        H3122     4-Cl-Ph          NH   C16          NH   OH             H        H3123     4-Cl-Ph          NH   F1           NH   OH             H        H3124     4-Cl-Ph          NH   F2           NH   OH             H        H3125     4-Cl-Ph          NH   F3           NH   OH             H        H3126     4-Cl-Ph          NH   F4           NH   OH             H        H3127     4-Cl-Ph          NH   F5           NH   OH             H        H3128     4-Cl-Ph          NH   F6           NH   OH             H        H3129     4-Cl-Ph          NH   F7           NH   OH             H        H3130     4-Cl-Ph          NH   F8           NH   OH             H        H3131     4-Cl-Ph          NH   F9           NH   OH             H        H3132     4-Cl-Ph          NH   F10          NH   OH             H        H3133     4-Cl-Ph          NH   Ph           NH   OH             H        H3134     4-Cl-Ph          NH   Bn           NH   OH             H        H3135     4-Cl-Ph       NH   Pe                 NH  OH                H   H3136     4-Cl-Ph       NH   C12                NMe OH                H   H3137     4-Cl-Ph       NH   C12                NEt OH                H   H3138     4-Cl-Ph       NH   C12                NPr OH                H   H3139     4-Cl-Ph       NH   (CH2)3          N   OH                H   H3140     4-Cl-Ph       NH   (CH2)4          N   OH                H   H3141     4-Cl-Ph       NH   (CH2)5          N   OH                H   H3142     4-Cl-Ph       NH   C12                O   OH                H   H3143     4-Cl-Ph       NH   Ph                 O   OH                H   H3144     4-Cl-Ph       NH   C12                S   OH                H   H3145     4-Cl-Ph       NH   Ph                 S   OH                H   H3146     4-Cl-Ph       NMe  H                  NH  OH                H   H3147     4-Cl-Ph       NEt  H                  NH  OH                H   H3148     4-Cl-Ph       NPr  H                  NH  OH                H   H3149     4-Cl-Ph       O    H                  NH  OH                H   H3150     4-Cl-Ph       S    H                  NH  OH                H   H3151     4-Br-Ph       NH   H                  NH  H                 H   H3152     4-Br-Ph       NH   H                  NH  OH                H   H3153     4-Br-Ph       NH   H                  NH  OA6               H   H3154     4-Br-Ph       NH   H                  NH  OA8               H   H3155     4-Br-Ph       NH   H                  NH  OA9               H   H3156     4-Br-Ph       NH   H                  NH  OA10              H   H3157     4-Br-Ph       NH   H                  NH  OA12              H   H3158     4-Br-Ph       NH   H                  NH  OA14              H   H3159     4-Br-Ph       NH   H                  NH  OA16              H   H3160     4-Br-Ph       NH   H                  NH  OH                H   A63161     4-Br-Ph       NH   H                  NH  OH                H   A83162     4-Br-Ph       NH   H                  NH  OH                H   A93163     4-Br-Ph       NH   H                  NH  OH                H   A103164     4-Br-Ph       NH   H           NH        OH               H    A123165     4-Br-Ph       NH   H           NH        OH               H    A143166     4-Br-Ph       NH   H           NH        OH               H    A163167     4-Br-Ph       NH   H           NH        OH               A6   A63168     4-Br-Ph       NH   H           NH        OH               A8   A83169     4-Br-Ph       NH   H           NH        OH               A10  A103170     4-Br-Ph       NH   H           H         OA2              A2   A23171     4-Br-Ph       NH   H           NH        OA3              A3   A33172     4-Br-Ph       NH   H           NH        OA4              A4   A43173     4-Br-Ph       NH   H           NH        OC6              H    H3174     4-Br-Ph       NH   H           NH        OC7              H    H3175     4-Br-Ph       NH   H           NH        OC8              H    H3176     4-Br-Ph       NH   H           NH        OC10             H    H3177     4-Br-Ph       NH   H           NH        OC11             H    H3178     4-Br-Ph       NH   H           NH        OC12             H    H3179     4-Br-Ph       NH   H           NH        OC14             H    H3180     4-Br-Ph       NH   H           NH        OC16             H    H3181     4-Br-Ph       NH   H           NH        C6CO3           H    H3182     4-Br-Ph       NH   H           NH        C7CO3           H    H3183     4-Br-Ph       NH   H           NH        C8CO3           H    H3184     4-Br-Ph       NH   H           NH        C9CO3           H    H3185     4-Br-Ph       NH   H           NH        C10CO3          H    H3186     4-Br-Ph       NH   H           NH        C12CO3          H    H3187     4-Br-Ph       NH   H           NH        C16CO3          H    H3188     4-Br-Ph       NH   C8          NH        OH               H    H3189     4-Br-Ph       NH   C9          NH        OH               H    H3190     4-Br-Ph       NH   C10         NH        OH               H    H3191     4-Br-Ph       NH   C12         NH        OH               H    H3192     4-Br-Ph       NH   C16         NH        OH               H    H3193     4-Br-Ph         NH   F1               NH   OH                H    H3194     4-Br-Ph         NH   F2               NH   OH                H    H3195     4-Br-Ph         NH   F3               NH   OH                H    H3196     4-Br-Ph         NH   F4               NH   OH                H    H3197     4-Br-Ph         NH   F5               NH   OH                H    H3198     4-Br-Ph         NH   F6               NH   OH                H    H3199     4-Br-Ph         NH   F7               NH   OH                H    H3200     4-Br-Ph         NH   F8               NH   OH                H    H3201     4-Br-Ph         NH   F9               NH   OH                H    H3202     4-Br-Ph         NH   F10              NH   OH                H    H3203     4-Br-Ph         NH   Ph               NH   OH                H    H3204     4-Br-Ph         NH   Bn               NH   OH                H    H3205     4-Br-Ph         NH   Pe               NH   OH                H    H3206     4-Br-Ph         NH   C12              NMe  OH                H    H3207     4-Br-Ph         NH   C12              NEt  OH                H    H3208     4-Br-Ph         NH   C12              NPr  OH                H    H3209     4-Br-Ph         NH   (CH2)3        N    OH                H    H3210     4-Br-Ph         NH   (CH2)4        N    OH                H    H3211     4-Br-Ph         NH   (CH2)5        N    OH                H    H3212     4-Br-Ph         NH   C12              O    OH                H    H3213     4-Br-Ph         NH   Ph               O    OH                H    H3214     4-Br-Ph         NH   C12              S    OH                H    H3215     4-Br-Ph         NH   Ph               S    OH                H    H3216     4-Br-Ph         NMe  H                NH   OH                H    H3217     4-Br-Ph         NEt  H                NH   OH                H    H3218     4-Br-Ph         NPr  H                NH   OH                H    H3219     4-Br-Ph         O    H                NH   OH                H    H3220     4-Br-Ph         S    H                NH   OH                H    H3221     4-I-Ph          NH   H                NH   H                 H    H3222   4-I-Ph                    NH      H            NH      OH          H        H3223   4-I-Ph                    NH      H            NH      OA6         H        H3224   4-I-Ph                    NH      H            NH      OA8         H        H3225   4-I-Ph                    NH      H            NH      OA9         H        H3226   4-I-Ph                    NH      H            NH      OA10        H        H3227   4-I-Ph                    NH      H            NH      OA12        H        H3228   4-I-Ph                    NH      H            NH      OA14        H        H3229   4-I-Ph                    NH      H            NH      OA16        H        H3230   4-I-Ph                    NH      H            NH      OH          H        A63231   4-I-Ph                    NH      H            NH      OH          H        A83232   4-I-Ph                    NH      H            NH      OH          H        A93233   4-I-Ph                    NH      H            NH      OH          H        A103234   4-I-Ph                    NH      H            NH      OH          H        A123235   4-I-Ph                    NH      H            NH      OH          H        A143236   4-I-Ph                    NH      H            NH      OH          H        A163237   4-I-Ph                    NH      H            NH      OH          A6       A63238   4-I-Ph                    NH      H            NH      OH          A8       A83239   4-I-Ph                    NH      H            NH      OH          A10      A103240   4-I-Ph                    NH      H            NH      OA2         A2       A23241   4-I-Ph                    NH      H            NH      OA3         A3       A33242   4-I-Ph                    NH      H            NH      OA4         A4       A43243   4-I-Ph                    NH      H            NH      OC6         H        H3244   4-I-Ph                    NH      H            NH      OC7         H        H3245   4-I-Ph                    NH      H            NH      OC8         H        H3246   4-I-Ph                    NH      H            NH      OC10        H        H3247   4-I-Ph                    NH      H            NH      OC11        H        H3248   4-I-Ph                    NH      H            NH      OC12        H        H3249   4-I-Ph                    NH      H            NH      OC14        H        H3250   4-I-Ph                    NH      H            NH      OC16        H        H3251     4-I-Ph        NH      H            NH      C6CO3        H   H3252     4-I-Ph        NH      H            NH      C7CO3        H   H3253     4-I-Ph        NH      H            NH      C8CO3        H   H3254     4-I-Ph        NH      H            NH      C9CO3        H   H3255     4-I-Ph        NH      H            NH      C10CO3       H   H3256     4-I-Ph        NH      H            NH      C12CO3       H   H3257     4-I-Ph        NH      H            NH      C16CO3       H   H3258     4-I-Ph        NH      C8           NH      OH            H   H3259     4-I-Ph        NH      C9           NH      OH            H   H3260     4-I-Ph        NH      C10          NH      OH            H   H3261     4-I-Ph        NH      C12          NH      OH            H   H3262     4-I-Ph        NH      C16          NH      OH            H   H3263     4-I-Ph        NH      F1           NH      OH            H   H3264     4-I-Ph        NH      F2           NH      OH            H   H3265     4-I-Ph        NH      F3           NH      OH            H   H3266     4-I-Ph        NH      F4           NH      OH            H   H3267     4-I-Ph        NH      F5           NH      OH            H   H3268     4-I-Ph        NH      F6           NH      OH            H   H3269     4-I-Ph        NH      F7           NH      OH            H   H3270     4-I-Ph        NH      F8           NH      OH            H   H3271     4-I-Ph        NH      F9           NH      OH            H   H3272     4-I-Ph        NH      F10          NH      OH            H   H3273     4-I-Ph        NH      Ph           NH      OH            H   H3274     4-I-Ph        NH      Bn           NH      OH            H   H3275     4-I-Ph        NH      Pe           NH      OH            H   H3276     4-I-Ph        NH      C12          NMe     OH            H   H3277     4-I-Ph        NH      C12          NEt     OH            H   H3278     4-I-Ph        NH      C12          NPr     OH            H   H3279     4-I-Ph        NH      (CH2)3    N       OH            H   H3280     4-I-Ph          NH   (CH2)4    N    OH            H        H3281     4-I-Ph          NH   (CH2)5    N    OH            H        H3282     4-I-Ph          NH   C12          O    OH            H        H3283     4-I-Ph          NH   Ph           O    OH            H        H3284     4-I-Ph          NH   C12          S    OH            H        H3285     4-I-Ph          NH   Ph           S    OH            H        H3286     4-I-Ph          NMe  H            NH   OH            H        H3287     4-I-Ph          NEt  H            NH   OH            H        H3288     4-I-Ph          NPr  H            NH   OH            H        H3289     4-I-Ph          O    H            NH   OH            H        H3290     4-I-Ph          S    H            NH   OH            H        H3291     3-Cl-Ph         NH   H            NH   H             H        H3292     3-Cl-Ph         NH   H            NH   OH            H        H3293     3-Cl-Ph         NH   H            NH   OA6           H        H3294     3-Cl-Ph         NH   H            NH   OA8           H        H3295     3-Cl-Ph         NH   H            NH   OA9           H        H3296     3-Cl-Ph         NH   H            NH   OA10          H        H3297     3-Cl-Ph         NH   H            NH   OA12          H        H3298     3-Cl-Ph         NH   H            NH   OA14          H        H3299     3-Cl-Ph         NH   H            NH   OA16          H        H3300     3-Cl-Ph         NH   H            NH   OH            H        A63301     3-Cl-Ph         NH   H            NH   OH            H        A83302     3-Cl-Ph         NH   H            NH   OH            H        A93303     3-Cl-Ph         NH   H            NH   OH            H        A103304     3-Cl-Ph         NH   H            NH   OH            H        A123305     3-Cl-Ph         NH   H            NH   OH            H        A143306     3-Cl-Ph         NH   H            NH   OH            H        A163307     3-Cl-Ph         NH   H            NH   OH            A6       A63308     3-Cl-Ph         NH   H            NH   OH            A8       A83309     3-Cl-Ph          NH   H            NH   OH            A10  A103310     3-Cl-Ph          NH   H            NH   OA2           A2   A23311     3-Cl-Ph          NH   H            NH   OA3           A3   A33312     3-Cl-Ph          NH   H            NH   OA4           A4   A43313     3-Cl-Ph          NH   H            NH   OC6           H    H3314     3-Cl-Ph          NH   H            NH   OC7           H    H3315     3-Cl-Ph          NH   H            NH   OC8           H    H3316     3-Cl-Ph          NH   H            NH   OC10          H    H3317     3-Cl-Ph          NH   H            NH   OC11          H    H3318     3-Cl-Ph          NH   H            NH   OC12          H    H3319     3-Cl-Ph          NH   H            NH   OC14          H    H3320     3-Cl-Ph          NH   H            NH   OC16          H    H3321     3-Cl-Ph          NH   H            NH   C6CO3        H    H3322     3-Cl-Ph          NH   H            NH   C7CO3        H    H3323     3-Cl-Ph          NH   H            NH   C8CO3        H    H3324     3-Cl-Ph          NH   H            NH   C9CO3        H    H3325     3-Cl-Ph          NH   H            NH   C10CO3       H    H3326     3-Cl-Ph          NH   H            NH   C12CO3       H    H3327     3-Cl-Ph          NH   H            NH   C16CO3       H    H3328     3-Cl-Ph          NH   C8           NH   OH            H    H3329     3-Cl-Ph          NH   C9           NH   OH            H    H3330     3-Cl-Ph          NH   C10          NH   OH            H    H3331     3-Cl-Ph          NH   C12          NH   OH            H    H3332     3-Cl-Ph          NH   C16          NH   OH            H    H3333     3-Cl-Ph          NH   F1           NH   OH            H    H3334     3-Cl-Ph          NH   F2           NH   OH            H    H3335     3-Cl-Ph          NH   F3           NH   OH            H    H3336     3-Cl-Ph          NH   F4           NH   OH            H    H3337     3-Cl-Ph          NH   F5           NH   OH            H    H3338     3-Cl-Ph         NH   F6              NH   OH               H    H3339     3-Cl-Ph         NH   F7              NH   OH               H    H3340     3-Cl-Ph         NH   F8              NH   OH               H    H3341     3-Cl-Ph         NH   F9              NH   OH               H    H3342     3-Cl-Ph         NH   F10             NH   OH               H    H3343     3-Cl-Ph         NH   Ph              NH   OH               H    H3344     3-Cl-Ph         NH   Bn              NH   OH               H    H3345     3-Cl-Ph         NH   Pe              NH   OH               H    H3346     3-Cl-Ph         NH   C12             NMe  OH               H    H3347     3-Cl-Ph         NH   C12             NEt  OH               H    H3348     3-Cl-Ph         NH   C12             NPr  OH               H    H3349     3-Cl-Ph         NH   (CH2)3       N    OH               H    H3350     3-Cl-Ph         NH   (CH2)4       N    OH               H    H3351     3-Cl-Ph         NH   (CH2)5       N    OH               H    H3352     3-Cl-Ph         NH   C12             O    OH               H    H3353     3-Cl-Ph         NH   Ph              O    OH               H    H3354     3-Cl-Ph         NH   C12             S    OH               H    H3355     3-Cl-Ph         NH   Ph              S    OH               H    H3356     3-Cl-Ph         NMe  H               NH   OH               H    H3357     3-Cl-Ph         NEt  H               NH   OH               H    H3358     3-Cl-Ph         NPr  H               NH   OH               H    H3359     3-Cl-Ph         O    H               NH   OH               H    H3360     3-Cl-Ph         S    H               NH   OH               H    H3361     3-I-Ph          NH   H               NH   H                H    H3362     3-I-Ph          NH   H               NH   OH               H    H3363     3-I-Ph          NH   H               NH   OA6              H    H3364     3-I-Ph          NH   H               NH   OA8              H    H3365     3-I-Ph          NH   H               NH   OA9              H    H3366     3-I-Ph          NH   H               NH   OA10             H    H3367   3-I-Ph                   NH       H            NH      OA12          H        H3368   3-I-Ph                   NH       H            NH      OA14          H        H3369   3-I-Ph                   NH       H            NH      OA16          H        H3370   3-I-Ph                   NH       H            NH      OH            H        A63371   3-I-Ph                   NH       H            NH      OH            H        A83372   3-I-Ph                   NH       H            NH      OH            H        A93373   3-I-Ph                   NH       H            NH      OH            H        A103374   3-I-Ph                   NH       H            NH      OH            H        A123375   3-I-Ph                   NH       H            NH      OH            H        A143376   3-I-Ph                   NH       H            NH      OH            H        A163377   3-I-Ph                   NH       H            NH      OH            A6       A63378   3-I-Ph                   NH       H            NH      OH            A8       A83379   3-I-Ph                   NH       H            NH      OH            A10      A103380   3-I-Ph                   NH       H            NH      OA2           A2       A23381   3-I-Ph                   NH       H            NH      OA3           A3       A33382   3-I-Ph                   NH       H            NH      OA4           A4       A43383   3-I-Ph                   NH       H            NH      OC6           H        H3384   3-I-Ph                   NH       H            NH      OC7           H        H3385   3-I-Ph                   NH       H            NH      OC8           H        H3386   3-I-Ph                   NH       H            NH      OC10          H        H3387   3-I-Ph                   NH       H            NH      OC11          H        H3388   3-I-Ph                   NH       H            NH      OC12          H        H3389   3-I-Ph                   NH       H            NH      OC14          H        H3390   3-I-Ph                   NH       H            NH      OC16          H        H3391   3-I-Ph                   NH       H            NH      C6CO3        H        H3392   3-I-Ph                   NH       H            NH      C7CO3        H        H3393   3-I-Ph                   NH       H            NH      C8CO3        H        H3394   3-I-Ph                   NH       H            NH      C9CO3        H        H3395   3-I-Ph                   NH       H            NH      C10CO3       H        H3396   3-I-Ph                     NH      H           NH       C12CO3        H        H3397   3-I-Ph                     NH      H           NH       C16CO3        H        H3398   3-I-Ph                     NH      C8          NH       OH             H        H3399   3-I-Ph                     NH      C9          NH       OH             H        H3400   3-I-Ph                     NH      C10         NH       OH             H        H3401   3-I-Ph                     NH      C12         NH       OH             H        H3402   3-I-Ph                     NH      C16         NH       OH             H        H3403   3-I-Ph                     NH      F1          NH       OH             H        H3404   3-I-Ph                     NH      F2          NH       OH             H        H3405   3-I-Ph                     NH      F3          NH       OH             H        H3406   3-I-Ph                     NH      F4          NH       OH             H        H3407   3-I-Ph                     NH      F5          NH       OH             H        H3408   3-I-Ph                     NH      F6          NH       OH             H        H3409   3-I-Ph                     NH      F7          NH       OH             H        H3410   3-I-Ph                     NH      F8          NH       OH             H        H3411   3-I-Ph                     NH      F9          NH       OH             H        H3412   3-I-Ph                     NH      F10         NH       OH             H        H3413   3-I-Ph                     NH      Ph          NH       OH             H        H3414   3-I-Ph                     NH      Bn          NH       OH             H        H3415   3-I-Ph                     NH      Pe          NH       OH             H        H3416   3-I-Ph                     NH      C12         NMe      OH             H        H3417   3-I-Ph                     NH      C12         NEt      OH             H        H3418   3-I-Ph                     NH      C12         NPr      OH             H        H3419   3-I-Ph                     NH      (CH2)3   N        OH             H        H3420   3-I-Ph                     NH      (CH2)4   N        OH             H        H3421   3-I-Ph                     NH      (CH2)5   N        OH             H        H3422   3-I-Ph                     NH      C12         O        OH             H        H3423   3-I-Ph                     NH      Ph          O        OH             H        H3424   3-I-Ph                     NH      C12         S        OH             H        H3425     3-I-Ph           NH   Ph           S    OH              H    H3426     3-I-Ph           He   H            NH   OH              H    H3427     3-I-Ph           NEt  H            NH   OH              H    H3428     3-I-Ph           NPr  H            NH   OH              H    H3429     3-I-Ph           O    H            NH   OH              H    H3430     3-I-Ph           S    H            NH   OH              H    H3431     2,3-F2-Ph      NH   H            NH   H               H    H3432     2,3-F2-Ph      NH   H            NH   OH              H    H3433     2,3-F2-Ph      NH   H            NH   OA6             H    H3434     2,3-F2-Ph      NH   H            NH   OA8             H    H3435     2,3-F2-Ph      NH   H            NH   OA9             H    H3436     2,3-F2-Ph      NH   H            NH   OA10            H    H3437     2,3-F2-Ph      NH   H            NH   OA12            H    H3438     2,3-F2-Ph      NH   H            NH   OA14            H    H3439     2,3-F2-Ph      NH   H            NH   OA16            H    H3440     2,3-F2-Ph      NH   H            NH   OH              H    A63441     2,3-F2-Ph      NH   H            NH   OH              H    A83442     2,3-F2-Ph      NH   H            NH   OH              H    A93443     2,3-F2-Ph      NH   H            NH   OH              H    A103444     2,3-F2-Ph      NH   H            NH   OH              H    A123445     2,3-F2-Ph      NH   H            NH   OH              H    A143446     2,3-F2-Ph      NH   H            NH   OH              H    A163447     2,3-F2-Ph      NH   H            NH   OH              A6   A63448     2,3-F2-Ph      NH   H            NH   OH              A8   A83449     2,3-F2-Ph      NH   H            NH   OH              A10  A103450     2,3-F2-Ph      NH   H            NH   OA2             A2   A23451     2,3-F2-Ph      NH   H            NH   OA3             A3   A33452     2,3-F2-Ph      NH   H            NH   OA4             A4   A43453     2,3-F2-Ph      NH   H            NH   OC6             H    H3454     2,3-F2-Ph      NH  H              NH    OC7               H     H3455     2,3-F2-Ph      NH  H              NH    OC8               H     H3456     2,3-F2-Ph      NH  H              NH    OC10              H     H3457     2,3-F2-Ph      NH  H              NH    OC11              H     H3458     2,3-F2-Ph      NH  H              NH    OC12              H     H3459     2,3-F2-Ph      NH  H              NH    OC14              H     H3460     2,3-F2-Ph      NH  H              NH    OC16              H     H3461     2,3-F2-Ph      NH  H              NH    C6CO3            H     H3462     2,3-F2-Ph      NH  H              NH    C7CO3            H     H3463     2,3-F2-Ph      NH  H              NH    C8CO3            H     H3464     2,3-F2-Ph      NH  H              NH    C9CO3            H     H3465     2,3-F2-Ph      NH  H              NH    C10CO3           H     H3466     2,3-F2-Ph      NH  H              NH    C12CO3           H     H3467     2,3-F2-Ph      NH  H              NH    C16CO3           H     H3468     2,3-F2-Ph      NH  C8             NH    OH                H     H3469     2,3-F2-Ph      NH  C9             NH    OH                H     H3470     2,3-F2-Ph      NH  C10            NH    OH                H     H3471     2,3-F2-Ph      NH  C12            NH    OH                H     H3472     2,3-F2-Ph      NH  C16            NH    OH                H     H3473     2,3-F2-Ph      NH  F1             NH    OH                H     H3474     2,3-F2-Ph      NH  F2             NH    OH                H     H3475     2,3-F2-Ph      NH  F3             NH    OH                H     H3476     2,3-F2-Ph      NH  F4             NH    OH                H     H3477     2,3-F2-Ph      NH  F5             NH    OH                H     H3478     2,3-F2-Ph      NH  F6             NH    OH                H     H3479     2,3-F2-Ph      NH  F7             NH    OH                H     H3480     2,3-F2-Ph      NH  F8             NH    OH                H     H3481     2,3-F2-Ph      NH  F9             NH    OH                H     H3482     2,3-F2-Ph      NH  F10            NH    OH                H     H3483     2,3-F2-Ph         NH    Ph            NH    OH             H     H3484     2,3-F2-Ph         NH    Bn            NH    OH             H     H3485     2,3-F2-Ph         NH    Pe            NH    OH             H     H3486     2,3-F2-Ph         NH    C12           NMe   OH             H     H3487     2,3-F2-Ph         NH    C12           NEt   OH             H     H3488     2,3-F2-Ph         NH    C12           NPr   OH             H     H3489     2,3-F2-Ph         NH    (CH2)3     N     OH             H     H3490     2,3-F2-Ph         NH    (CH2)4     N     OH             H     H3491     2,3-F2-Ph         NH    (CH2)5     N     OH             H     H3492     2,3-F2-Ph         NH    C12           O     OH             H     H3493     2,3-F2-Ph         NH    Ph            O     OH             H     H3494     2,3-F2-Ph         NH    C12           S     OH             H     H3495     2,3-F2-Ph         NH    Ph            S     OH             H     H3496     2,3-F2-Ph         NMe   H             NH    OH             H     H3497     2,3-F2-Ph         NEt   H             NH    OH             H     H3498     2,3-F2-Ph         NPr   H             NH    OH             H     H3499     2,3-F2-Ph         O     H             NH    OH             H     H3500     2,3-F2-Ph         S     H             NH    OH             H     H3501     2,4-F2-Ph         NH    H             NH    H              H     H3502     2,4-F2-Ph         NH    H             NH    OH             H     H3503     2,4-F2-Ph         NH    H             NH    OA6            H     H3504     2,4-F2-Ph         NH    H             NH    OA8            H     H3505     2,4-F2-Ph         NH    H             NH    OA9            H     H3506     2,4-F2-Ph         NH    H             NH    OA10           H     H3507     2,4-F2-Ph         NH    H             NH    OA12           H     H3508     2,4-F2-Ph         NH    H             NH    OA14           H     H3509     2,4-F2-Ph         NH    H             NH    OA16           H     H3510     2,4-F2-Ph         NH    H             NH    OH             H     A63511     2,4-F2-Ph         NH    H             NH    OH             H     A83512      2,4-F2-Ph        NH   H           NH   OH              H    A93513      2,4-F2-Ph        NH   H           NH   OH              H    A103514      2,4-F2-Ph        NH   H           NH   OH              H    A123515      2,4-F2-Ph        NH   H           NH   OH              H    A143516      2,4-F2-Ph        NH   H           NH   OH              H    A163517      2,4-F2-Ph        NH   H           NH   OH              A6   A63518      2,4-F2-Ph        NH   H           NH   OH              A8   A83519      2,4-F2-Ph        NH   H           NH   OH              A10  A103520      2,4-F2-Ph        NH   H           NH   OA2             A2   A23521      2,4-F2-Ph        NH   H           NH   OA3             A3   A33522      2,4-F2-Ph        NH   H           NH   OA4             A4   A43523      2,4-F2-Ph        NH   H           NH   OC6             H    H3524      2,4-F2-Ph        NH   H           NH   OC7             H    H3525      2,4-F2-Ph        NH   H           NH   OC8             H    H3526      2,4-F2-Ph        NH   H           NH   OC10            H    H3527      2,4-F2-Ph        NH   H           NH   OC11            H    H3528      2,4-F2-Ph        NH   H           NH   OC12            H    H3529      2,4-F2-Ph        NH   H           NH   OC14            H    H3530      2,4-F2-Ph        NH   H           NH   OC16            H    H3531      2,4-F2-Ph        NH   H           NH   C6CO3          H    H3532      2,4-F2-Ph        NH   H           NH   C7CO3          H    H3533      2,4-F2-Ph        NH   H           NH   C8CO3          H    H3534      2,4-F2-Ph        NH   H           NH   C9CO3          H    H3535      2,4-F2-Ph        NH   H           NH   C10CO3         H    H3536      2,4-F2-Ph        NH   H           NH   C12CO3         H    H3537      2,4-F2-Ph        NH   H           NH   C16CO3         H    H3538      2,4-F2-Ph        NH   C8          NH   OH              H    H3539      2,4-F2-Ph        NH   C9          NH   OH              H    H3540      2,4-F2-Ph        NH   C10         NH   OH              H    H3541      2,4-F2-Ph      NH      C12           NH  OH             H   H3542      2,4-F2-Ph      NH      C16           NH  OH             H   H3543      2,4-F2-Ph      NH      F1            NH  OH             H   H3544      2,4-F2-Ph      NH      F2            NH  OH             H   H3545      2,4-F2-Ph      NH      F3            NH  OH             H   H3546      2,4-F2-Ph      NH      F4            NH  OH             H   H3547      2,4-F2-Ph      NH      F5            NH  OH             H   H3548      2,4-F2-Ph      NH      F6            NH  OH             H   H3549      2,4-F2-Ph      NH      F7            NH  OH             H   H3550      2,4-F2-Ph      NH      F8            NH  OH             H   H3551      2,4-F2-Ph      NH      F9            NH  OH             H   H3552      2,4-F2-Ph      NH      F10           NH  OH             H   H3553      2,4-F2-Ph      NH      Ph            NH  OH             H   H3554      2,4-F2-Ph      NH      Bn            NH  OH             H   H3555      2,4-F2-Ph      NH      Pe            NH  OH             H   H3556      2,4-F2-Ph      NH      C12           NMe OH             H   H3557      2,4-F2-Ph      NH      C12           NEt OH             H   H3558      2,4-F2-Ph      NH      C12           NPr OH             H   H3559      2,4-F2-Ph      NH      (CH2)3     N   OH             H   H3560      2,4-F2-Ph      NH      (CH2)4     N   OH             H   H3561      2,4-F2-Ph      NH      (CH2)5     N   OH             H   H3562      2,4-F2-Ph      NH      C12           O   OH             H   H3563      2,4-F2-Ph      NH      Ph            O   OH             H   H3564      2,4-F2-Ph      NH      C12           S   OH             H   H3565      2,4-F2-Ph      NH      Ph            S   OH             H   H3566      2,4-F2-Ph      NMe     H             NH  OH             H   H3567      2,4-F2-Ph      NEt     H             NH  OH             H   H3568      2,4-F2-Ph      NPr     H             NH  OH             H   H3569      2,4-F2-Ph      O       H             NH  OH             H   H3570     2,4-F2-Ph      S    H         NH   OH                 H        H3571     2,5-F2-Ph      NH   H         NH   H                  H        H3572     2,5-F2-Ph      NH   H         NH   OH                 H        H3573     2,5-F2-Ph      NH   H         NH   OA6                H        H3574     2,5-F2-Ph      NH   H         NH   OA8                H        H3575     2,5-F2-Ph      NH   H         NH   OA9                H        H3576     2,5-F2-Ph      NH   H         NH   OA10               H        H3577     2,5-F2-Ph      NH   H         NH   OA12               H        H3578     2,5-F2-Ph      NH   H         NH   OA14               H        H3579     2,5-F2-Ph      NH   H         NH   OA16               H        H3580     2,5-F2-Ph      NH   H         NH   OH                 H        A63581     2,5-F2-Ph      NH   H         NH   OH                 H        A83582     2,5-F2-Ph      NH   H         NH   OH                 H        A93583     2,5-F2-Ph      NH   H         NH   OH                 H        A103584     2,5-F2-Ph      NH   H         NH   OH                 H        A123585     2,5-F2-Ph      NH   H         NH   OH                 H        A143586     2,5-F2-Ph      NH   H         NH   OH                 H        A163587     2,5-F2-Ph      NH   H         NH   OH                 A6       A63588     2,5-F2-Ph      NH   H         NH   OH                 A8       A83589     2,5-F2-Ph      NH   H         NH   OH                 A10      A103590     2,5-F2-Ph      NH   H         NH   OA2                A2       A23591     2,5-F2-Ph      NH   H         NH   OA3                A3       A33592     2,5-F2-Ph      NH   H         NH   OA4                A4       A43593     2,5-F2-Ph      NH   H         NH   OC6                H        H3594     2,5-F2-Ph      NH   H         NH   OC7                H        H3595     2,5-F2-Ph      NH   H         NH   OC8                H        H3596     2,5-F2-Ph      NH   H         NH   OC10               H        H3597     2,5-F2-Ph      NH   H         NH   OC11               H        H3598     2,5-F2-Ph      NH   H         NH   OC12               H        H3599  2,5-F2-Ph         NH    H          NH    OC14              H     H3600  2,5-F2-Ph         NH    H          NH    OC16              H     H3601  2,5-F2-Ph         NH    H          NH    C6CO3            H     H3602  2,5-F2-Ph         NH    H          NH    C7CO3            H     H3603  2,5-F2-Ph         NH    H          NH    C8CO3            H     H3604  2,5-F2-Ph         NH    H          NH    C9CO3            H     H3605  2,5-F2-Ph         NH    H          NH    C10CO3           H     H3606  2,5-F2-Ph         NH    H          NH    C12CO3           H     H3607  2,5-F2-Ph         NH    H          NH    C16CO3           H     H3608  2,5-F2-Ph         NH    C8         NH    OH                H     H3609  2,5-F2-Ph         NH    C9         NH    OH                H     H3610  2,5-F2-Ph         NH    C10        NH    OH                H     H3611  2,5-F2-Ph         NH    C12        NH    OH                H     H3612  2,5-F2-Ph         NH    C16        NH    OH                H     H3613  2,5-F2-Ph         NH    F1         NH    OH                H     H3614  2,5-F2-Ph         NH    F2         NH    OH                H     H3615  2,5-F2-Ph         NH    F3         NH    OH                H     H3616  2,5-F2-Ph         NH    F4         NH    OH                H     H3617  2,5-F2-Ph         NH    F5         NH    OH                H     H3618  2,5-F2-Ph         NH    F6         NH    OH                H     H3619  2,5-F2-Ph         NH    F7         NH    OH                H     H3620  2,5-F2-Ph         NH    F8         NH    OH                H     H3621  2,5-F2-Ph         NH    F9         NH    OH                H     H3622  2,5-F2-Ph         NH    F10        NH    OH                H     H3623  2,5-F2-Ph         NH    Ph         NH    OH                H     H3624  2,5-F2-Ph         NH    Bn         NH    OH                H     H3625  2,5-F2-Ph         NH    Pe         NH    OH                H     H3626  2,5-F2-Ph         NH    C12        NMe   OH                H     H3627  2,5-F2-Ph         NH    C12        NEt   OH                H     H3628  2,5-F2-Ph      NH       C12            NPr     OH            H   H3629  2,5-F2-Ph      NH       (CH2)3      N       OH            H   H3630  2,5-F2-Ph      NH       (CH2)4      N       OH            H   H3631  2,5-F2-Ph      NH       (CH2)5      N       OH            H   H3632  2,5-F2-Ph      NH       C12            O       OH            H   H3633  2,5-F2-Ph      NH       Ph             O       OH            H   H3634  2,5-F2-Ph      NH       C12            S       OH            H   H3635  2,5-F2-Ph      NH       Ph             S       OH            H   H3636  2,5-F2-Ph      NMe      H              NH      OH            H   H3637  2,5-F2-Ph      NEt      H              NH      OH            H   H3638  2,5-F2-Ph      NPr      H              NH      OH            H   H3639  2,5-F2-Ph      O        H              NH      OH            H   H3640  2,5-F2-Ph      S        H              NH      OH            H   H3641  2,6-F2-Ph      NH       H              NH      H             H   H3642  2,6-F2-Ph      NH       H              NH      OH            H   H3643  2,6-F2-Ph      NH       H              NH      OA6           H   H3644  2,6-F2-Ph      NH       H              NH      OA8           H   H3645  2,6-F2-Ph      NH       H              NH      OA9           H   H3646  2,6-F2-Ph      NH       H              NH      OA10          H   H3647  2,6-F2-Ph      NH       H              NH      OA12          H   H3648  2,6-F2-Ph      NH       H              NH      OA14          H   H3649  2,6-F2-Ph      NH       H              NH      OA16          H   H3650  2,6-F2-Ph      NH       H              NH      OH            H   A63651  2,6-F2-Ph      NH       H              NH      OH            H   A83652  2,6-F2-Ph      NH       H              NH      OH            H   A93653  2,6-F2-Ph      NH       H              NH      OH            H   A103654  2,6-F2-Ph      NH       H              NH      OH            H   A123655  2,6-F2-Ph      NH       H              NH      OH            H   A143656  2,6-F2-Ph      NH       H              NH      OH            H   A163657      2,6-F2-Ph        NH   H             NH   OH             A6   A63658      2,6-F2-Ph        NH   H             NH   OH             A8   A83659      2,6-F2-Ph        NH   H             NH   OH             A10  A103660      2,6-F2-Ph        NH   H             NH   OA2            A2   A23661      2,6-F2-Ph        NH   H             NH   OA3            A3   A33662      2,6-F2-Ph        NH   H             NH   OA4            A4   A43663      2,6-F2-Ph        NH   H             NH   OC6            H    H3664      2,6-F2-Ph        NH   H             NH   OC7            H    H3665      2,6-F2-Ph        NH   H             NH   OC8            H    H3666      2,6-F2-Ph        NH   H             NH   OC10           H    H3667      2,6-F2-Ph        NH   H             NH   OC11           H    H3668      2,6-F2-Ph        NH   H             NH   OC12           H    H3669      2,6-F2-Ph        NH   H             NH   OC14           H    H3670      2,6-F2-Ph        NH   H             NH   OC16           H    H3671      2,6-F2-Ph        NH   H             NH   C6CO3         H    H3672      2,6-F2-Ph        NH   H             NH   C7CO3         H    H3673      2,6-F2-Ph        NH   H             NH   C8CO3         H    H3674      2,6-F2-Ph        NH   H             NH   C9CO3         H    H3675      2,6-F2-Ph        NH   H             NH   C10CO3        H    H3676      2,6-F2-Ph        NH   H             NH   C12CO3        H    H3677      2,6-F2-Ph        NH   H             NH   C16CO3        H    H3678      2,6-F2-Ph        NH   C8            NH   OH             H    H3679      2,6-F2-Ph        NH   C9            NH   OH             H    H3680      2,6-F2-Ph        NH   C10           NH   OH             H    H3681      2,6-F2-Ph        NH   C12           NH   OH             H    H3682      2,6-F2-Ph        NH   C16           NH   OH             H    H3683      2,6-F2-Ph        NH   F1            NH   OH             H    H3684      2,6-F2-Ph        NH   F2            NH   OH             H    H3685      2,6-F2-Ph        NH   F3            NH   OH             H    H3686     2,6-F2-Ph       NH   F4              NH   OH              H   H3687     2,6-F2-Ph       NH   F5              NH   OH              H   H3688     2,6-F2-Ph       NH   F6              NH   OH              H   H3689     2,6-F2-Ph       NH   F7              NH   OH              H   H3690     2,6-F2-Ph       NH   F8              NH   OH              H   H3691     2,6-F2-Ph       NH   F9              NH   OH              H   H3692     2,6-F2-Ph       NH   F10             NH   OH              H   H3693     2,6-F2-Ph       NH   Ph              NH   OH              H   H3694     2,6-F2-Ph       NH   Bn              NH   OH              H   H3695     2,6-F2-Ph       NH   Pe              NH   OH              H   H3696     2,6-F2-Ph       NH   C12             NHe  OH              H   H3697     2,6-F2-Ph       NH   C12             NEt  OH              H   H3698     2,6-F2-Ph       NH   C12             NPr  OH              H   H3699     2,6-F2-Ph       NH   (CH2)3       N    OH              H   H3700     2,6-F2-Ph       NH   (CH2)4       N    OH              H   H3701     2,6-F2-Ph       NH   (CH2)5       N    OH              H   H3702     2,6-F2-Ph       NH   C12             O    OH              H   H3703     2,6-F2-Ph       NH   Ph              O    OH              H   H3704     2,6-F2-Ph       NH   C12             S    OH              H   H3705     2,6-F2-Ph       NH   Ph              S    OH              H   H3706     2,6-F2-Ph       NMe  H               NH   OH              H   H3707     2,6-F2-Ph       NEt  H               NH   OH              H   H3708     2,6-F2-Ph       NPr  H               NH   OH              H   H3709     2,6-F2-Ph       O    H               NH   OH              H   H3710     2,6-F2-Ph       S    H               NH   OH              H   H3711     3,4-F2-Ph       NH   H               NH   H               H   H3712     3,4-F2-Ph       NH   H               NH   OH              H   H3713     3,4-F2-Ph       NH   H               NH   OA6             H   H3714     3,4-F2-Ph       NH   H               NH   OA8             H   H3715     3,4-F2-Ph       NH   H               NH   OA9              H    H3716     3,4-F2-Ph       NH   H               NH   OA10             H    H3717     3,4-F2-Ph       NH   H               NH   OA12             H    H3718     3,4-F2-Ph       NH   H               NH   OA14             H    H3719     3,4-F2-Ph       NH   H               NH   OA16             H    H3720     3,4-F2-Ph       NH   H               NH   OH               H    A63721     3,4-F2-Ph       NH   H               NH   OH               H    A83722     3,4-F2-Ph       NH   H               NH   OH               H    A93723     3,4-F2-Ph       NH   H               NH   OH               H    A103724     3,4-F2-Ph       NH   H               NH   OH               H    A123725     3,4-F2-Ph       NH   H               NH   OH               H    A143726     3,4-F2-Ph       NH   H               NH   OH               H    A163727     3,4-F2-Ph       NH   H               NH   OH               A6   A63728     3,4-F2-Ph       NH   H               NH   OH               A8   A83729     3,4-F2-Ph       NH   H               NH   OH               A10  A103730     3,4-F2-Ph       NH   H               NH   OA2              A2   A23731     3,4-F2-Ph       NH   H               NH   OA3              A3   A33732     3,4-F2-Ph       NH   H               NH   OA4              A4   A43733     3,4-F2-Ph       NH   H               NH   OC6              H    H3734     3,4-F2-Ph       NH   H               NH   OC7              H    H3735     3,4-F2-Ph       NH   H               NH   OC8              H    H3736     3,4-F2-Ph       NH   H               NH   OC10             H    H3737     3,4-F2-Ph       NH   H               NH   OC11             H    H3738     3,4-F2-Ph       NH   H               NH   OC12             H    H3739     3,4-F2-Ph       NH   H               NH   OC14             H    H3740     3,4-F2-Ph       NH   H               NH   OC16             H    H3741     3,4-F2-Ph       NH   H               NH   C6CO3           H    H3742     3,4-F2-Ph       NH   H               NH   C7CO3           H    H3743     3,4-F2-Ph       NH   H               NH   C8CO3           H    H3744     3,4-F2-Ph      NH  H             NH      C9CO3        H   H3745     3,4-F2-Ph      NH  H             NH      C10CO3       H   H3746     3,4-F2-Ph      NH  H             NH      C12CO3       H   H3747     3,4-F2-Ph      NH  H             NH      C16CO3       H   H3748     3,4-F2-Ph      NH  C8            NH      OH            H   H3749     3,4-F2-Ph      NH  C9            NH      OH            H   H3750     3,4-F2-Ph      NH  C10           NH      OH            H   H3751     3,4-F2-Ph      NH  C12           NH      OH            H   H3752     3,4-F2-Ph      NH  C16           NH      OH            H   H3753     3,4-F2-Ph      NH  F1            NH      OH            H   H3754     3,4-F2-Ph      NH  F2            NH      OH            H   H3755     3,4-F2-Ph      NH  F3            NH      OH            H   H3756     3,4-F2-Ph      NH  F4            NH      OH            H   H3757     3,4-F2-Ph      NH  F5            NH      OH            H   H3758     3,4-F2-Ph      NH  F6            NH      OH            H   H3759     3,4-F2-Ph      NH  F7            NH      OH            H   H3760     3,4-F2-Ph      NH  F8            NH      OH            H   H3761     3,4-F2-Ph      NH  F9            NH      OH            H   H3762     3,4-F2-Ph      NH  F10           NH      OH            H   H3763     3,4-F2-Ph      NH  Ph            NH      OH            H   H3764     3,4-F2-Ph      NH  Bn            NH      OH            H   H3765     3,4-F2-Ph      NH  Pe            NH      OH            H   H3766     3,4-F2-Ph      NH  C12           NMe     OH            H   H3767     3,4-F2-Ph      NH  C12           NEt     OH            H   H3768     3,4-F2-Ph      NH  C12           NPr     OH            H   H3769     3,4-F2-Ph      NH  (CH2)3     N       OH            H   H3770     3,4-F2-Ph      NH  (CH2)4     N       OH            H   H3771     3,4-F2-Ph      NH  (CH2)5     N       OH            H   H3772     3,4-F2-Ph      NH  C12           O       OH            H   H3773     3,4-F2-Ph       NH    Ph         O        OH          H       H3774     3,4-F2-Ph       NH    C12        S        OH          H       H3775     3,4-F2-Ph       NH    Ph         S        OH          H       H3776     3,4-F2-Ph       NMe   H          NH       OH          H       H3777     3,4-F2-Ph       NEt   H          NH       OH          H       H3778     3,4-F2-Ph       NPr   H          NH       OH          H       H3779     3,4-F2-Ph       O     H          NH       OH          H       H3780     3,4-F2-Ph       S     H          NH       OH          H       H3781     3,5-F2-Ph       NH    H          NH       H           H       H3782     3,5-F2-Ph       NH    H          NH       OH          H       H3783     3,5-F2-Ph       NH    H          NH       OA6         H       H3784     3,5-F2-Ph       NH    H          NH       OA8         H       H3785     3,5-F2-Ph       NH    H          NH       OA9         H       H3786     3,5-F2-Ph       NH    H          NH       OA10        H       H3787     3,5-F2-Ph       NH    H          NH       OA12        H       H3788     3,5-F2-Ph       NH    H          NH       OA14        H       H3789     3,5-F2-Ph       NH    H          NH       OA16        H       H3790     3,5-F2-Ph       NH    H          NH       OH          H       A63791     3,5-F2-Ph       NH    H          NH       OH          H       A83792     3,5-F2-Ph       NH    H          NH       OH          H       A93793     3,5-F2-Ph       NH    H          NH       OH          H       A103794     3,5-F2-Ph       NH    H          NH       OH          H       A123795     3,5-F2-Ph       NH    H          NH       OH          H       A143796     3,5-F2-Ph       NH    H          NH       OH          H       A163797     3,5-F2-Ph       NH    H          NH       OH          A6      A63798     3,5-F2-Ph       NH    H          NH       OH          A8      A83799     3,5-F2-Ph       NH    H          NH       OH          A10     A103800     3,5-F2-Ph       NH    H          NH       OA2         A2      A23801     3,5-F2-Ph       NH    H          NH       OA3         A3      A33802     3,5-F2-Ph      NH   H            NH     OA4             A4  A43803     3,5-F2-Ph      NH   H            NH     OC6             H   H3804     3,5-F2-Ph      NH   H            NH     OC7             H   H3805     3,5-F2-Ph      NH   H            NH     OC8             H   H3806     3,5-F2-Ph      NH   H            NH     OC10            H   H3807     3,5-F2-Ph      NH   H            NH     OC11            H   H3808     3,5-F2-Ph      NH   H            NH     OC12            H   H3809     3,5-F2-Ph      NH   H            NH     OC14            H   H3810     3,5-F2-Ph      NH   H            NH     OC16            H   H3811     3,5-F2-Ph      NH   H            NH     C6CO3          H   H3812     3,5-F2-Ph      NH   H            NH     C7CO3          H   H3813     3,5-F2-Ph      NH   H            NH     C8CO3          H   H3814     3,5-F2-Ph      NH   H            NH     C9CO3          H   H3815     3,5-F2-Ph      NH   H            NH     C10CO3         H   H3816     3,5-F2-Ph      NH   H            NH     C12CO3         H   H3817     3,5-F2-Ph      NH   H            NH     C16CO3         H   H3818     3,5-F2-Ph      NH   C8           NH     OH              H   H3819     3,5-F2-Ph      NH   C9           NH     OH              H   H3820     3,5-F2-Ph      NH   C10          NH     OH              H   H3821     3,5-F2-Ph      NH   C12          NH     OH              H   H3822     3,5-F2-Ph      NH   C16          NH     OH              H   H3823     3,5-F2-Ph      NH   F1           NH     OH              H   H3824     3,5-F2-Ph      NH   F2           NH     OH              H   H3825     3,5-F2-Ph      NH   F3           NH     OH              H   H3826     3,5-F2-Ph      NH   F4           NH     OH              H   H3827     3,5-F2-Ph      NH   F5           NH     OH              H   H3828     3,5-F2-Ph      NH   F6           NH     OH              H   H3829     3,5-F2-Ph      NH   F7           NH     OH              H   H3830     3,5-F2-Ph      NH   F8           NH     OH              H   H3831   3,5-F2-Ph             NH      F9          NH       OH           H        H3832   3,5-F2-Ph             NH      F10         NH       OH           H        H3833   3,5-F2-Ph             NH      Ph          NH       OH           H        H3834   3,5-F2-Ph             NH      Bn          NH       OH           H        H3835   3,5-F2-Ph             NH      Pe          NH       OH           H        H3836   3,5-F2-Ph             NH      C12         NMe      OH           H        H3837   3,5-F2-Ph             NH      C12         NEt      OH           H        H3838   3,5-F2-Ph             NH      C12         NPr      OH           H        H3839   3,5-F2-Ph             NH      (CH2)3   N        OH           H        H3840   3,5-F2-Ph             NH      (CH2)4   N        OH           H        H3841   3,5-F2-Ph             NH      (CH2)5   N        OH           H        H3842   3,5-F2-Ph             NH      C12         O        OH           H        H3843   3,5-F2-Ph             NH      Ph          O        OH           H        H3844   3,5-F2-Ph             NH      C12         S        OH           H        H3845   3,5-F2-Ph             NH      Ph          S        OH           H        H3846   3,5-F2-Ph             NMe     H           NH       OH           H        H3847   3,5-F2-Ph             NEt     H           NH       OH           H        H3848   3,5-F2-Ph             NPr     H           NH       OH           H        H3849   3,5-F2-Ph             O       H           NH       OH           H        H3850   3,5-F2-Ph             S       H           NH       OH           H        H3851   2,3,4-F3-Ph          NH      H           NH       H            H        H3852   2,3,4-F3-Ph          NH      H           NH       OH           H        H3853   2,3,4-F3-Ph          NH      H           NH       OA6          H        H3854   2,3,4-F3-Ph          NH      H           NH       OA8          H        H3855   2,3,4-F3-Ph          NH      H           NH       OA9          H        H3856   2,3,4-F3-Ph          NH      H           NH       OA10         H        H3857   2,3,4-F3-Ph          NH      H           NH       OA12         H        H3858   2,3,4-F3-Ph          NH      H           NH       OA14         H        H3859   2,3,4-F3-Ph          NH      H           NH       OA16         H        H3860     2,3,4-F3-Ph       NH    H       NH    OH              H     A63861     2,3,4-F3-Ph       NH    H       NH    OH              H     A83862     2,3,4-F3-Ph       NH    H       NH    OH              H     A93863     2,3,4-F3-Ph       NH    H       NH    OH              H     A103864     2,3,4-F3-Ph       NH    H       NH    OH              H     A123865     2,3,4-F3-Ph       NH    H       NH    OH              H     A143866     2,3,4-F3-Ph       NH    H       NH    OH              H     A163867     2,3,4-F3-Ph       NH    H       NH    OH              A6    A63868     2,3,4-F3-Ph       NH    H       NH    OH              A8    A83869     2,3,4-F3-Ph       NH    H       NH    OH              A10   A103870     2,3,4-F3-Ph       NH    H       NH    OA2             A2    A23871     2,3,4-F3-Ph       NH    H       NH    OA3             A3    A33872     2,3,4-F3-Ph       NH    H       NH    OA4             A4    A43873     2,3,4-F3-Ph       NH    H       NH    OC6             H     H3874     2,3,4-F3-Ph       NH    H       NH    OC7             H     H3875     2,3,4-F3-Ph       NH    H       NH    OC8             H     H3876     2,3,4-F3-Ph       NH    H       NH    OC10            H     H3877     2,3,4-F3-Ph       NH    H       NH    OC11            H     H3878     2,3,4-F3-Ph       NH    H       NH    OC12            H     H3879     2,3,4-F3-Ph       NH    H       NH    OC14            H     H3880     2,3,4-F3-Ph       NH    H       NH    OC16            H     H3881     2,3,4-F3-Ph       NH    H       NH    C6CO3          H     H3882     2,3,4-F3-Ph       NH    H       NH    C7CO3          H     H3883     2,3,4-F3-Ph       NH    H       NH    C8CO3          H     H3884     2,3,4-F3-Ph       NH    H       NH    C9CO3          H     H3885     2,3,4-F3-Ph       NH    H       NH    C10CO3         H     H3886     2,3,4-F3-Ph       NH    H       NH    C12CO3         H     H3887     2,3,4-F3-Ph       NH    H       NH    C16CO3         H     H3888     2,3,4-F3-Ph       NH    C8      NH    OH              H     H3889     2,3,4-F3-Ph     NH   C9              NH   OH              H   H3890     2,3,4-F3-Ph     NH   C10             NH   OH              H   H3891     2,3,4-F3-Ph     NH   C12             NH   OH              H   H3892     2,3,4-F3-Ph     NH   C16             NH   OH              H   H3893     2,3,4-F3-Ph     NH   F1              NH   OH              H   H3894     2,3,4-F3-Ph     NH   F2              NH   OH              H   H3895     2,3,4-F3-Ph     NH   F3              NH   OH              H   H3896     2,3,4-F3-Ph     NH   F4              NH   OH              H   H3897     2,3,4-F3-Ph     NH   F5              NH   OH              H   H3898     2,3,4-F3-Ph     NH   F6              NH   OH              H   H3899     2,3,4-F3-Ph     NH   F7              NH   OH              H   H3900     2,3,4-F3-Ph     NH   F8              NH   OH              H   H3901     2,3,4-F3-Ph     NH   F9              NH   OH              H   H3902     2,3,4-F3-Ph     NH   F10             NH   OH              H   H3903     2,3,4-F3-Ph     NH   Ph              NH   OH              H   H3904     2,3,4-F3-Ph     NH   Bn              NH   OH              H   H3905     2,3,4-F3-Ph     NH   Pe              NH   OH              H   H3906     2,3,4-F3-Ph     NH   C12             NMe  OH              H   H3907     2,3,4-F3-Ph     NH   C12             NEt  OH              H   H3908     2,3,4-F3-Ph     NH   C12             NPr  OH              H   H3909     2,3,4-F3-Ph     NH   (CH2)3       N    OH              H   H3910     2,3,4-F3-Ph     NH   (CH2)4       N    OH              H   H3911     2,3,4-F3-Ph     NH   (CH2)5       N    OH              H   H3912     2,3,4-F3-Ph     NH   C12             O    OH              H   H3913     2,3,4-F3-Ph     NH   Ph              O    OH              H   H3914     2,3,4-F3-Ph     NH   C12             S    OH              H   H3915     2,3,4-F3-Ph     NH   Ph              S    OH              H   H3916     2,3,4-F3-Ph     NMe  H               NH   OH              H   H3917     2,3,4-F3-Ph     NEt  H               NH   OH              H   H3918     2,3,4-F3-Ph     NPr  H               NH   OH               H   H3919     2,3,4-F3-Ph     O    H               NH   OH               H   H3920     2,3,4-F3-Ph     S    H               NH   OH               H   H3921     2,3,6-F3-Ph     NH   H               NH   H                H   H3922     2,3,6-F3-Ph     NH   H               NH   OH               H   H3923     2,3,6-F3-Ph     NH   H               NH   OA6              H   H3924     2,3,6-F3-Ph     NH   H               NH   OA8              H   H3925     2,3,6-F3-Ph     NH   H               NH   OA9              H   H3926     2,3,6-F3-Ph     NH   H               NH   OA10             H   H3927     2,3,6-F3-Ph     NH   H               NH   OA12             H   H3928     2,3,6-F3-Ph     NH   H               NH   OA14             H   H3929     2,3,6-F3-Ph     NH   H               NH   OA16             H   H3930     2,3,6-F3-Ph     NH   H               NH   OH               H   A63931     2,3,6-F3-Ph     NH   H               NH   OH               H   A83932     2,3,6-F3-Ph     NH   H               NH   OH               H   A93933     2,3,6-F3-Ph     NH   H               NH   OH               H   A103934     2,3,6-F3-Ph     NH   H               NH   OH               H   A123935     2,3,6-F3-Ph     NH   H               NH   OH               H   A143936     2,3,6-F3-Ph     NH   H               NH   OH               H   A163937     2,3,6-F3-Ph     NH   H               NH   OH               A6  A63938     2,3,6-F3-Ph     NH   H               NH   OH               A8  A83939     2,3,6-F3-Ph     NH   H               NH   OH               A10 A103940     2,3,6-F3-Ph     NH   H               NH   OA2              A2  A23941     2,3,6-F3-Ph     NH   H               NH   OA3              A3  A33942     2,3,6-F3-Ph     NH   H               NH   OA4              A4  A43943     2,3,6-F3-Ph     NH   H               NH   OC6              H   H3944     2,3,6-F3-Ph     NH   H               NH   OC7              H   H3945     2,3,6-F3-Ph     NH   H               NH   OC8              H   H3946     2,3,6-F3-Ph     NH   H               NH   OC10             H   H3947     2,3,6-F3-Ph     NH   H               NH   OC11           H    H3948     2,3,6-F3-Ph     NH   H               NH   OC12           H    H3949     2,3,6-F3-Ph     NH   H               NH   OC14           H    H3950     2,3,6-F3-Ph     NH   H               NH   OC16           H    H3951     2,3,6-F3-Ph     NH   H               NH   C6CO3         H    H3952     2,3,6-F3-Ph     NH   H               NH   C7CO3         H    H3953     2,3,6-F3-Ph     NH   H               NH   C8CO3         H    H3954     2,3,6-F3-Ph     NH   H               NH   C9CO3         H    H3955     2,3,6-F3-Ph     NH   H               NH   C10CO3        H    H3956     2,3,6-F3-Ph     NH   H               NH   C12CO3        H    H3957     2,3,6-F3-Ph     NH   H               NH   C16CO3        H    H3958     2,3,6-F3-Ph     NH   C8              NH   OH             H    H3959     2,3,6-F3-Ph     NH   C9              NH   OH             H    H3960     2,3,6-F3-Ph     NH   C10             NH   OH             H    H3961     2,3,6-F3-Ph     NH   C12             NH   OH             H    H3962     2,3,6-F3-Ph     NH   C16             NH   OH             H    H3963     2,3,6-F3-Ph     NH   F1              NH   OH             H    H3964     2,3,6-F3-Ph     NH   F2              NH   OH             H    H3965     2,3,6-F3-Ph     NH   F3              NH   OH             H    H3966     2,3,6-F3-Ph     NH   F4              NH   OH             H    H3967     2,3,6-F3-Ph     NH   F5              NH   OH             H    H3968     2,3,6-F3-Ph     NH   F6              NH   OH             H    H3969     2,3,6-F3-Ph     NH   F7              NH   OH             H    H3970     2,3,6-F3-Ph     NH   F8              NH   OH             H    H3971     2,3,6-F3-Ph     NH   F9              NH   OH             H    H3972     2,3,6-F3-Ph     NH   F10             NH   OH             H    H3973     2,3,6-F3-Ph     NH   Ph              NH   OH             H    H3974     2,3,6-F3-Ph     NH   Bn              NH   OH             H    H3975     2,3,6-F3-Ph     NH   Pe              NH   OH             H    H3976     2,3,6-F3-Ph      NH        C12         NMe  OH           H    H3977     2,3,6-F3-Ph      NH        C12         NEt  OH           H    H3978     2,3,6-F3-Ph      NH        C12         NPr  OH           H    H3979     2,3,6-F3-Ph      NH        (CH2)3   N    OH           H    H3980     2,3,6-F3-Ph      NH        (CH2)4   N    OH           H    H3981     2,3,6-F3-Ph      NH        (CH2)5   N    OH           H    H3982     2,3,6-F3-Ph      NH        C12         O    OH           H    H3983     2,3,6-F3-Ph      NH        Ph          O    OH           H    H3984     2,3,6-F3-Ph      NH        C12         S    OH           H    H3985     2,3,6-F3-Ph      NH        Ph          S    OH           H    H3986     2,3,6-F3-Ph      NMe       H           NH   OH           H    H3987     2,3,6-F3-Ph      NEt       H           NH   OH           H    H3988     2,3,6-F3-Ph      NPr       H           NH   OH           H    H3989     2,3,6-F3-Ph      O         H           NH   OH           H    H3990     2,3,6-F3-Ph      S         H           NH   OH           H    H3991     2,4,6-F3-Ph      NH        H           NH   H            H    H3992     2,4,6-F3-Ph      NH        H           NH   OH           H    H3993     2,4,6-F3-Ph      NH        H           NH   OA6          H    H3994     2,4,6-F3-Ph      NH        H           NH   OA8          H    H3995     2,4,6-F3-Ph      NH        H           NH   OA9          H    H3996     2,4,6-F3-Ph      NH        H           NH   OA10         H    H3997     2,4,6-F3-Ph      NH        H           NH   OA12         H    H3998     2,4,6-F3-Ph      NH        H           NH   OA14         H    H3999     2,4,6-F3-Ph      NH        H           NH   OA16         H    H4000     2,4,6-F3-Ph      NH        H           NH   OH           H    A64001     2,4,6-F3-Ph      NH        H           NH   OH           H    A84002     2,4,6-F3-Ph      NH        H           NH   OH           H    A94003     2,4,6-F3-Ph      NH        H           NH   OH           H    A104004     2,4,6-F3-Ph      NH        H           NH   OH           H    A124005     2,4,6-F3-Ph       NH    H       NH   OH              H       A144006     2,4,6-F3-Ph       NH    H       NH   OH              H       A164007     2,4,6-F3-Ph       NH    H       NH   OH              A6      A64008     2,4,6-F3-Ph       NH    H       NH   OH              A8      A84009     2,4,6-F3-Ph       NH    H       NH   OH              A10     A104010     2,4,6-F3-Ph       NH    H       NH   OA2             A2      A24011     2,4,6-F3-Ph       NH    H       NH   OA3             A3      A34012     2,4,6-F3-Ph       NH    H       NH   OA4             A4      A44013     2,4,6-F3-Ph       NH    H       NH   OC6             H       H4014     2,4,6-F3-Ph       NH    H       NH   OC7             H       H4015     2,4,6-F3-Ph       NH    H       NH   OC8             H       H4016     2,4,6-F3-Ph       NH    H       NH   OC10            H       H4017     2,4,6-F3-Ph       NH    H       NH   OC11            H       H4018     2,4,6-F3-Ph       NH    H       NH   OC12            H       H4019     2,4,6-F3-Ph       NH    H       NH   OC14            H       H4020     2,4,6-F3-Ph       NH    H       NH   OC16            H       H4021     2,4,6-F3-Ph       NH    H       NH   C6CO3          H       H4022     2,4,6-F3-Ph       NH    H       NH   C7CO3          H       H4023     2,4,6-F3-Ph       NH    H       NH   C8CO3          H       H4024     2,4,6-F3-Ph       NH    H       NH   C9CO3          H       H4025     2,4,6-F3-Ph       NH    H       NH   C10CO3         H       H4026     2,4,6-F3-Ph       NH    H       NH   C12CO3         H       H4027     2,4,6-F3-Ph       NH    H       NH   C16CO3         H       H4028     2,4,6-F3-Ph       NH    C8      NH   OH              H       H4029     2,4,6-F3-Ph       NH    C9      NH   OH              H       H4030     2,4,6-F3-Ph       NH    C10     NH   OH              H       H4031     2,4,6-F3-Ph       NH    C12     NH   OH              H       H4032     2,4,6-F3-Ph       NH    C16     NH   OH              H       H4033     2,4,6-F3-Ph       NH    F1      NH   OH              H       H4034     2,4,6-F3-Ph    NH   F2              NH     OH              H   H4035     2,4,6-F3-Ph    NH   F3              NH     OH              H   H4036     2,4,6-F3-Ph    NH   F4              NH     OH              H   H4037     2,4,6-F3-Ph    NH   F5              NH     OH              H   H4038     2,4,6-F3-Ph    NH   F6              NH     OH              H   H4039     2,4,6-F3-Ph    NH   F7              NH     OH              H   H4040     2,4,6-F3-Ph    NH   F8              NH     OH              H   H4041     2,4,6-F3-Ph    NH   F9              NH     OH              H   H4042     2,4,6-F3-Ph    NH   F10             NH     OH              H   H4043     2,4,6-F3-Ph    NH   Ph              NH     OH              H   H4044     2,4,6-F3-Ph    NH   Bn              NH     OH              H   H4045     2,4,6-F3-Ph    NH   Pe              NH     OH              H   H4046     2,4,6-F3-Ph    NH   C12             NMe    OH              H   H4047     2,4,6-F3-Ph    NH   C12             NEt    OH              H   H4048     2,4,6-F3-Ph    NH   C12             NPr    OH              H   H4049     2,4,6-F3-Ph    NH   (CH2)3       N      OH              H   H4050     2,4,6-F3-Ph    NH   (CH2)4       N      OH              H   H4051     2,4,6-F3-Ph    NH   (CH2)3       N      OH              H   H4052     2,4,6-F3-Ph    NH   C12             O      OH              H   H4053     2,4,6-F3-Ph    NH   Ph              O      OH              H   H4054     2,4,6-F3-Ph    NH   C12             S      OH              H   H4055     2,4,6-F3-Ph    NH   Ph              S      OH              H   H4056     2,4,6-F3-Ph    NMe  H               NH     OH              H   H4057     2,4,6-F3-Ph    NEt  H               NH     OH              H   H4058     2,4,6-F3-Ph    NPr  H               NH     OH              H   H4059     2,4,6-F3-Ph    O    H               NH     OH              H   H4060     2,4,6-F3-Ph    S    H               NH     OH              H   H4061     2,4,5-F3-Ph    NH   H               NH     H               H   H4062     2,4,5-F3-Ph    NH   H               NH     OH              H   H4063      2,4,5-F3-Ph       NH     H        NH         OA6         H     H4064      2,4,5-F3-Ph       NH     H        NH         OA8         H     H4065      2,4,5-F3-Ph       NH     H        NH         OA9         H     H4066      2,4,5-F3-Ph       NH     H        NH         OA10        H     H4067      2,4,5-F3-Ph       NH     H        NH         OA12        H     H4068      2,4,5-F3-Ph       NH     H        NH         OA14        H     H4069      2,4,5-F3-Ph       NH     H        NH         OA16        H     H4070      2,4,5-F3-Ph       NH     H        NH         OH          H     A64071      2,4,5-F3-Ph       NH     H        NH         OH          H     A84072      2,4,5-F3-Ph       NH     H        NH         OH          H     A94073      2,4,5-F3-Ph       NH     H        NH         OH          H     A104074      2,4,5-F3-Ph       NH     H        NH         OH          H     A124075      2,4,5-F3-Ph       NH     H        NH         OH          H     A144076      2,4,5-F3-Ph       NH     H        NH         OH          H     A164077      2,4,5-F3-Ph       NH     H        NH         OH          A6    A64078      2,4,5-F3-Ph       NH     H        NH         OH          A8    A84079      2,4,5-F3-Ph       NH     H        NH         OH          A10   A104080      2,4,5-F3-Ph       NH     H        NH         OA2         A2    A24081      2,4,5-F3-Ph       NH     H        NH         OA3         A3    A34082      2,4,5-F3-Ph       NH     H        NH         OA4         A4    A44083      2,4,5-F3-Ph       NH     H        NH         OC6         H     H4084      2,4,5-F3-Ph       NH     H        NH         OC7         H     H4085      2,4,5-F3-Ph       NH     H        NH         OC8         H     H4086      2,4,5-F3-Ph       NH     H        NH         OC10        H     H4087      2,4,5-F3-Ph       NH     H        NH         OC11        H     H4088      2,4,5-F3-Ph       NH     H        NH         OC12        H     H4089      2,4,5-F3-Ph       NH     H        NH         OC14        H     H4090      2,4,5-F3-Ph       NH     H        NH         OC16        H     H4091      2,4,5-F3-Ph       NH     H        NH         C6CO3      H     H4092     2,4,5-F3-Ph    NH  H                 NH   C7CO3       H    H4093     2,4,5-F3-Ph    NH  H                 NH   C8CO3       H    H4094     2,4,5-F3-Ph    NH  H                 NH   C9CO3       H    H4095     2,4,5-F3-Ph    NH  H                 NH   C10CO3      H    H4096     2,4,5-F3-Ph    NH  H                 NH   C12CO3      H    H4097     2,4,5-F3-Ph    NH  H                 NH   C16CO3      H    H4098     2,4,5-F3-Ph    NH  C8                NH   OH           H    H4099     2,4,5-F3-Ph    NH  C9                NH   OH           H    H4100     2,4,5-F3-Ph    NH  C10               NH   OH           H    H4101     2,4,5-F3-Ph    NH  C12               NH   OH           H    H4102     2,4,5-F3-Ph    NH  C16               NH   OH           H    H4103     2,4,5-F3-Ph    NH  F1                NH   OH           H    H4104     2,4,5-F3-Ph    NH  F2                NH   OH           H    H4105     2,4,5-F3-Ph    NH  F3                NH   OH           H    H4106     2,4,5-F3-Ph    NH  F4                NH   OH           H    H4107     2,4,5-F3-Ph    NH  F5                NH   OH           H    H4108     2,4,5-F3-Ph    NH  F6                NH   OH           H    H4109     2,4,5-F3-Ph    NH  F7                NH   OH           H    H4110     2,4,5-F3-Ph    NH  F8                NH   OH           H    H4111     2,4,5-F3-Ph    NH  F9                NH   OH           H    H4112     2,4,5-F3-Ph    NH  F10               NH   OH           H    H4113     2,4,5-F3-Ph    NH  Ph                NH   OH           H    H4114     2,4,5-F3-Ph    NH  Bn                NH   OH           H    H4115     2,4,5-F3-Ph    NH  Pe                NH   OH           H    H4116     2,4,5-F3-Ph    NH  C12               NMe  OH           H    H4117     2,4,5-F3-Ph    NH  C12               NEt  OH           H    H4118     2,4,5-F3-Ph    NH  C12               NPr  OH           H    H4119     2,4,5-F3-Ph    NH  (CH2)3         N    OH           H    H4120     2,4,5-F3-Ph    NH  (CH2)4         N   OH            H    H4121   2,4,5-F3-Ph   NH      (CH2)5    N        OH            H       H4122   2,4,5-F3-Ph   NH      C12          O        OH            H       H4123   2,4,5-F3-Ph   NH      Ph           O        OH            H       H4124   2,4,5-F3-Ph   NH      C12          S        OH            H       H4125   2,4,5-F3-Ph   NH      Ph           S        OH            H       H4126   2,4,5-F3-Ph   Me      H            NH       OH            H       H4127   2,4,5-F3-Ph   NEt     H            NH       OH            H       H4128   2,4,5-F3-Ph   NPr     H            NH       OH            H       H4129   2,4,5-F3-Ph   O       H            NH       OH            H       H4130   2,4,5-F3-Ph   S       H            NH       OH            H       H4131   3-Cl-4-F-Ph      NH      H            NH       H             H       H4132   3-Cl-4-F-Ph      NH      H            NH       OH            H       H4133   3-Cl-4-F-Ph      NH      H            NH       OA6           H       H4134   3-Cl-4-F-Ph      NH      H            NH       OA8           H       H4135   3-Cl-4-F-Ph      NH      H            NH       OA9           H       H4136   3-Cl-4-F-Ph      NH      H            NH       OA10          H       H4137   3-Cl-4-F-Ph      NH      H            NH       OA12          H       H4138   3-Cl-4-F-Ph      NH      H            NH       OA14          H       H4139   3-Cl-4-F-Ph      NH      H            NH       OA16          H       H4140   3-Cl-4-F-Ph      NH      H            NH       OH            H       A64141   3-Cl-4-F-Ph      NH      H            NH       OH            H       A84142   3-Cl-4-F-Ph      NH      H            NH       OH            H       A94143   3-Cl-4-F-Ph      NH      H            NH       OH            H       A104144   3-Cl-4-F-Ph      NH      H            NH       OH            H       A124145   3-Cl-4-F-Ph      NH      H            NH       OH            H       A144146   3-Cl-4-F-Ph      NH      H            NH       OH            H       A164147   3-Cl-4-F-Ph      NH      H            NH       OH            A6      A64148   3-Cl-4-F-Ph      NH      H            NH       OH            A8      A84149   3-Cl-4-F-Ph      NH      H            NH       OH            A10     A104150   3-Cl-4-F-Ph             NH           H     NH   OA2          A2   A24151   3-Cl-4-F-Ph             NH           H     NH   OA3          A3   A34152   3-Cl-4-F-Ph             NH           H     NH   OA4          A4   A44153   3-Cl-4-F-Ph             NH           H     NH   OC6          H    H4154   3-Cl-4-F-Ph             NH           H     NH   OC7          H    H4155   3-Cl-4-F-Ph             NH           H     NH   OC8          H    H4156   3-Cl-4-F-Ph             NH           H     NH   OC10         H    H4157   3-Cl-4-F-Ph             NH           H     NH   OC11         H    H4158   3-Cl-4-F-Ph             NH           H     NH   OC12         H    H4159   3-Cl-4-F-Ph             NH           H     NH   OC14         H    H4160   3-Cl-4-F-Ph             NH           H     NH   OC16         H    H4161   3-Cl-4-F-Ph             NH           H     NH   C6CO3       H    H4162   3-Cl-4-F-Ph             NH           H     NH   C7CO3       H    H4163   3-Cl-4-F-Ph             NH           H     NH   C8CO3       H    H4164   3-Cl-4-F-Ph             NH           H     NH   C9CO3       H    H4165   3-Cl-4-F-Ph             NH           H     NH   C10CO3      H    H4166   3-Cl-4-F-Ph             NH           H     NH   C12CO3      H    H4167   3-Cl-4-F-Ph             NH           H     NH   C16CO3      H    H4168   3-Cl-4-F-Ph             NH           C8    NH   OH           H    H4169   3-Cl-4-F-Ph             NH           C9    NH   OH           H    H4170   3-Cl-4-F-Ph             NH           C10   NH   OH           H    H4171   3-Cl-4-F-Ph             NH           C12   NH   OH           H    H4172   3-Cl-4-F-Ph             NH           C16   NH   OH           H    H4173   3-Cl-4-F-Ph             NH           F1    NH   OH           H    H4174   3-Cl-4-F-Ph             NH           F2    NH   OH           H    H4175   3-Cl-4-F-Ph             NH           F3    NH   OH           H    H4176   3-Cl-4-F-Ph             NH           F4    NH   OH           H    H4177   3-Cl-4-F-Ph             NH           F5    NH   OH           H    H4178   3-Cl-4-F-Ph             NH           F6    NH   OH           H    H4179   3-Cl-4-F-Ph      NH   F7            NH          OH          H        H4180   3-Cl-4-F-Ph      NH   F8            NH          OH          H        H4181   3-Cl-4-F-Ph      NH   F9            NH          OH          H        H4182   3-Cl-4-F-Ph      NH   Fl0           NH          OH          H        H4183   3-Cl-4-F-Ph      NH   Ph            NH          OH          H        H4184   3-Cl-4-F-Ph      NH   Bn            NH          OH          H        H4185   3-Cl-4-F-Ph      NH   Pe            NH          OH          H        H4186   3-Cl-4-F-Ph      NH   C12           NMe         OH          H        H4187   3-Cl-4-F-Ph      NH   C12           NEt         OH          H        H4188   3-Cl-4-F-Ph      NH   C12           NPr         OH          H        H4189   3-Cl-4-F-Ph      NH   (CH2)3     N           OH          H        H4190   3-Cl-4-F-Ph      NH   (CH2)4     N           OH          H        H4191   3-Cl-4-F-Ph      NH   (CH2)5     N           OH          H        H4192   3-Cl-4-F-Ph      NH   C12           O           OH          H        H4193   3-Cl-4-F-Ph      NH   Ph            O           OH          H        H4194   3-Cl-4-F-Ph      NH   C12           S           OH          H        H4195   3-Cl-4-F-Ph      NH   Ph            S           OH          H        H4196   3-Cl-4-F-Ph      NMe  H             NH          OH          H        H4197   3-Cl-4-F-Ph      NEt  H             NH          OH          H        H4198   3-Cl-4-F-Ph      NPr  H             NH          OH          H        H4199   3-Cl-4-F-Ph      O    H             NH          OH          H        H4200   3-Cl-4-F-Ph      S    H             NH          OH          H        H4201   3-CF3-4-F-Ph    NH   H             NH          H           H        H4202   3-CF3-4-F-Ph    NH   H             NH          OH          H        H4203   3-CF3-4-F-Ph    NH   H             NH          OA6         H        H4204   3-CF3-4-F-Ph    NH   H             NH          OA8         H        H4205   3-CF3-4-F-Ph    NH   H             NH          OA9         H        H4206   3-CF3-4-F-Ph    NH   H             NH          OA10        H        H4207   3-CF3-4-F-Ph    NH   H             NH          OA12        H        H4208   3-CF3-4-F-Ph         NH      H           NH    OA14        H       H4209   3-CF3-4-F-Ph         NH      H           NH    OA16        H       H4210   3-CF3-4-F-Ph         NH      H           NH    OH          H       A64211   3-CF3-4-F-Ph         NH      H           NH    OH          H       A84212   3-CF3-4-F-Ph         NH      H           NH    OH          H       A94213   3-CF3-4-F-Ph         NH      H           NH    OH          H       A104214   3-CF3-4-F-Ph         NH      H           NH    OH          H       A124215   3-CF3-4-F-Ph         NH      H           NH    OH          H       A144216   3-CF3-4-F-Ph         NH      H           NH    OH          H       A164217   3-CF3-4-F-Ph         NH      H           NH    OH          A6      A64218   3-CF3-4-F-Ph         NH      H           NH    OH          A8      A84219   3-CF3-4-F-Ph         NH      H           NH    OH          A10     A104220   3-CF3-4-F-Ph         NH      H           NH    OA2         A2      A24221   3-CF3-4-F-Ph         NH      H           NH    OA3         A3      A34222   3-CF3-4-F-Ph         NH      H           NH    OA4         A4      A44223   3-CF3-4-F-Ph         NH      H           NH    OC6         H       H4224   3-CF3-4-F-Ph         NH      H           NH    OC7         H       H4225   3-CF3-4-F-Ph         NH      H           NH    OC8         H       H4226   3-CF3-4-F-Ph         NH      H           NH    OC10        H       H4227   3-CF3-4-F-Ph         NH      H           NH    OC11        H       H4228   3-CF3-4-F-Ph         NH      H           NH    OC12        H       H4229   3-CF3-4-F-Ph         NH      H           NH    OC14        H       H4230   3-CF3-4-F-Ph         NH      H           NH    OC16        H       H4231   3-CF3-4-F-Ph         NH      H           NH    C6CO3      H       H4232   3-CF3-4-F-Ph         NH      H           NH    C7CO3      H       H4233   3-CF3-4-F-Ph         NH      H           NH    C8CO3      H       H4234   3-CF3-4-F-Ph         NH      H           NH    C9CO3      H       H4235   3-CF3-4-F-Ph         NH      H           NH    C10CO3     H       H4236   3-CF3-4-F-Ph         NH      H           NH    C12CO3     H       H4237  3-CF3-4-F-Ph      NH   H               NH   C16CO3        H    H4238  3-CF3-4-F-Ph      NH   C8              NH   OH             H    H4239  3-CF3-4-F-Ph      NH   C9              NH   OH             H    H4240  3-CF3-4-F-Ph      NH   C10             NH   OH             H    H4241  3-CF3-4-F-Ph      NH   C12             NH   OH             H    H4242  3-CF3-4-F-Ph      NH   C16             NH   OH             H    H4243  3-CF3-4-F-Ph      NH   F1              NH   OH             H    H4244  3-CF3-4-F-Ph      NH   F2              NH   OH             H    H4245  3-CF3-4-F-Ph      NH   F3              NH   OH             H    H4246  3-CF3-4-F-Ph      NH   F4              NH   OH             H    H4247  3-CF3-4-F-Ph      NH   F5              NH   OH             H    H4248  3-CF3-4-F-Ph      NH   F6              NH   OH             H    H4249  3-CF3-4-F-Ph      NH   F7              NH   OH             H    H4250  3-CF3-4-F-Ph      NH   F8              NH   OH             H    H4251  3-CF3-4-F-Ph      NH   F9              NH   OH             H    H4252  3-CF3-4-F-Ph      NH   F10             NH   OH             H    H4253  3-CF3-4-F-Ph      NH   Ph              NH   OH             H    H4254  3-CF3-4-F-Ph      NH   Bn              NH   OH             H    H4255  3-CF3-4-F-Ph      NH   Pe              NH   OH             H    H4256  3-CF3-4-F-Ph      NH   C12             NMe  OH             H    H4257  3-CF3-4-F-Ph      NH   C12             NEt  OH             H    H4258  3-CF3-4-F-Ph      NH   C12             NPr  OH             H    H4259  3-CF3-4-F-Ph      NH   (CH2)3       N    OH             H    H4260  3-CF3-4-F-Ph      NH   (CH2)4       N    OH             H    H4261  3-CF3-4-F-Ph      NH   (CH2)5       N    OH             H    H4262  3-CF3-4-F-Ph      NH    C12            O    OH             H    H4263  3-CF3-4-F-Ph      NH    Ph             O    OH             H    H4264  3-CF3-4-F-Ph      NH    C12            S    OH             H    H4265  3-CF3-4-F-Ph      NH    Ph             S    OH             H    H4266   3-CF3-4-F-Ph    He      H        NH      OH           H            H4267   3-CF3-4-F-Ph    NEt     H        NH      OH           H            H4268   3-CF3-4-F-Ph    NPr     H        NH      OH           H            H4269   3-CF3-4-F-Ph    O       H        NH      OH           H            H4270   3-CF3-4-F-Ph    S       H        NH      OH           H            H4271   3-CF3O-Ph       NH      H        NH      H            H            H4272   3-CF3O-Ph       NH      H        NH      OH           H            H4273   3-CF3O-Ph       NH      H        NH      OA6          H            H4274   3-CF3O-Ph       NH      H        NH      OA8          H            H4275   3-CF3O-Ph       NH      H        NH      OA9          H            H4276   3-CF3O-Ph       NH      H        NH      OA10         H            H4277   3-CF3O-Ph       NH      H        NH      OA12         H            H4278   3-CF3O-Ph       NH      H        NH      OA14         H            H4279   3-CF3O-Ph       NH      H        NH      OA16         H            H4280   3-CF3O-Ph       NH      H        NH      OH           H            A64281   3-CF3O-Ph       NH      H        NH      OH           H            A84282   3-CF3O-Ph       NH      H        NH      OH           H            A94283   3-CF3O-Ph       NH      H        NH      OH           H            A104284   3-CF3O-Ph       NH      H        NH      OH           H            A124285   3-CF3O-Ph       NH      H        NH      OH           H            A144286   3-CF3O-Ph       NH      H        NH      OH           H            A164287   3-CF3O-Ph       NH      H        NH      OH           A6           A64288   3-CF3O-Ph       NH      H        NH      OH           A8           A84289   3-CF3O-Ph       NH      H        NH      OH           A10          A104290   3-CF3O-Ph       NH      H        NH      OA2          A2           A24291   3-CF3O-Ph       NH      H        NH      OA3          A3           A34292   3-CF3O-Ph       NH      H        NH      OA4          A4           A44293   3-CF3O-Ph       NH      H        NH      OC6          H            H4294   3-CF3O-Ph       NH      H        NH      OC7          H            H4295   3-CF3O-Ph         NH   H              NH   OC8           H          H4296   3-CF3O-Ph         NH   H              NH   OC10          H          H4297   3-CF3O-Ph         NH   H              NH   OC11          H          H4298   3-CF3O-Ph         NH   H              NH   OC12          H          H4299   3-CF3O-Ph         NH   H              NH   OC14          H          H4300   3-CF3O-Ph         NH   H              NH   OC16          H          H4301   3-CF3O-Ph         NH   H              NH   C6CO3        H          H4302   3-CF3O-Ph         NH   H              NH   C7CO3        H          H4303   3-CF3O-Ph         NH   H              NH   C8CO3        H          H4304   3-CF3O-Ph         NH   H              NH   C9CO3        H          H4305   3-CF3O-Ph         NH   H              NH   C10CO3       H          H4306   3-CF3O-Ph         NH   H              NH   C12CO3       H          H4307   3-CF3O-Ph         NH   H              NH   C16CO3       H          H4308   3-CF3O-Ph         NH   C8             NH   OH            H          H4309   3-CF3O-Ph         NH   C9             NH   OH            H          H4310   3-CF3O-Ph         NH   C10            NH   OH            H          H4311   3-CF3O-Ph         NH   C12            NH   OH            H          H4312   3-CF3O-Ph         NH   C16            NH   OH            H          H4313   3-CF3O-Ph         NH   F1             NH   OH            H          H4314   3-CF3O-Ph         NH   F2             NH   OH            H          H4315   3-CF3O-Ph         NH   F3             NH   OH            H          H4316   3-CF3O-Ph         NH   F4             NH   OH            H          H4317   3-CF3O-Ph         NH   F5             NH   OH            H          H4318   3-CF3O-Ph         NH   F6             NH   OH            H          H4319   3-CF3O-Ph         NH   F7             NH   OH            H          H4320   3-CF3O-Ph         NH   F8             NH   OH            H          H4321   3-CF3O-Ph         NH   F9             NH   OH            H          H4322   3-CF3O-Ph         NH   F10            NH   OH            H          H4323   3-CF3O-Ph         NH   Ph             NH   OH            H          H4324    3-CF3O-Ph        NH    Bn            NH    OH            H    H4325    3-CF3O-Ph        NH    Pe            NH    OH            H    H4326    3-CF3O-Ph        NH    C12           NMe   OH            H    H4327    3-CF3O-Ph        NH    C12           NEt   OH            H    H4328    3-CF3O-Ph        NH    C12           NPr   OH            H    H4329    3-CF3O-Ph        NH    (CH2)3     N     OH            H    H4330    3-CF3O-Ph        NH    (CH2)4     N     OH            H    H4331    3-CF3O-Ph        NH    (CH2)5     N     OH            H    H4332    3-CF3O-Ph        NH    C12           O     OH            H    H4333    3-CF3O-Ph        NH    Ph            O     OH            H    H4334    3-CF3O-Ph        NH    C12           S     OH            H    H4335    3-CF3O-Ph        NH    Ph            S     OH            H    H4336    3-CF3O-Ph        NMe   H             NH    OH            H    H4337    3-CF3O-Ph        NEt   H             NH    OH            H    H4338    3-CF3O-Ph        NPr   H             NH    OH            H    H4339    3-CF3O-Ph        O     H             NH    OH            H    H4340    3-CF3O-Ph        S     H             NH    OH            H    H4341    4-CF3O-Ph        NH    H             NH    H             H    H4342    4-CF3O-Ph        NH    H             NH    OH            H    H4343    4-CF3O-Ph        NH    H             NH    OA6           H    H4344    4-CF3O-Ph        NH    H             NH    OA8           H    H4345    4-CF3O-Ph        NH    H             NH    OA9           H    H4346    4-CF3O-Ph        NH    H             NH    OA10          H    H4347    4-CF3O-Ph        NH    H             NH    OA12          H    H4348    4-CF3O-Ph        NH    H             NH    OA14          H    H4349    4-CF3O-Ph        NH    H             NH    OA16          H    H4350    4-CF3O-Ph        NH    H             NH    OH            H    A64351    4-CF3O-Ph        NH    H             NH    OH            H    A84352    4-CF3O-Ph        NH    H             NH    OH            H    A94353  4-CF3O-Ph        NH    H           NH    OH            H     A104354  4-CF3O-Ph        NH    H           NH    OH            H     A124355  4-CF3O-Ph        NH    H           NH    OH            H     A144356  4-CF3O-Ph        NH    H           NH    OH            H     A164357  4-CF3O-Ph        NH    H           NH    OH            A6    A64358  4-CF3O-Ph        NH    H           NH    OH            A8    A84359  4-CF3O-Ph        NH    H           NH    OH            A10   A104360  4-CF3O-Ph        NH    H           NH    OA2           A2    A24361  4-CF3O-Ph        NH    H           NH    OA3           A3    A34362  4-CF3O-Ph        NH    H           NH    OA4           A4    A44363  4-CF3O-Ph        NH    H           NH    OC6           H     H4364  4-CF3O-Ph        NH    H           NH    OC7           H     H4365  4-CF3O-Ph        NH    H           NH    OC8           H     H4366  4-CF3O-Ph        NH    H           NH    OC10          H     H4367  4-CF3O-Ph        NH    H           NH    OC11          H     H4368  4-CF3O-Ph        NH    H           NH    OC12          H     H4369  4-CF3O-Ph        NH    H           NH    OC14          H     H4370  4-CF3O-Ph        NH    H           NH    OC16          H     H4371  4-CF3O-Ph        NH    H           NH    C6CO3        H     H4372  4-CF3O-Ph        NH    H           NH    C7CO3        H     H4373  4-CF3O-Ph        NH    H           NH    C8CO3        H     H4374  4-CF3O-Ph        NH    H           NH    C9CO3        H     H4375  4-CF3O-Ph        NH    H           NH    C10CO3       H     H4376  4-CF3O-Ph        NH    H           NH    C12CO3       H     H4377  4-CF3O-Ph        NH    H           NH    C16CO3       H     H4378  4-CF3O-Ph        NH    C8          NH    OH            H     H4379  4-CF3O-Ph        NH    C9          NH    OH            H     H4380  4-CF3O-Ph        NH    C10         NH    OH            H     H4381  4-CF3O-Ph        NH    C12         NH    OH            H     H4382   4-CF3O-Ph       NH      C16          NH         OH          H    H4383   4-CF3O-Ph       NH      F1           NH         OH          H    H4384   4-CF3O-Ph       NH      F2           NH         OH          H    H4385   4-CF3O-Ph       NH      F3           NH         OH          H    H4386   4-CF3O-Ph       NH      F4           NH         OH          H    H4387   4-CF3O-Ph       NH      F5           NH         OH          H    H4388   4-CF3O-Ph       NH      F6           NH         OH          H    H4389   4-CF3O-Ph       NH      F7           NH         OH          H    H4390   4-CF3O-Ph       NH      F8           NH         OH          H    H4391   4-CF3O-Ph       NH      F9           NH         OH          H    H4392   4-CF3O-Ph       NH      F10          NH         OH          H    H4393   4-CF3O-Ph       NH      Ph           NH         OH          H    H4394   4-CF3O-Ph       NH      Bn           NH         OH          H    H4395   4-CF3O-Ph       NH      Pe           NH         OH          H    H4396   4-CF3O-Ph       NH      C12          NMe        OH          H    H4397   4-CF3O-Ph       NH      C12          NEt        OH          H    H4398   4-CF3O-Ph       NH      C12          NPr        OH          H    H4399   4-CF3O-Ph       NH      (CH2)3    N          OH          H    H4400   4-CF3O-Ph       NH      (CH2)4    N          OH          H    H4401   4-CF3O-Ph       NH      (CH2)5    N          OH          H    H4402   4-CF3O-Ph       NH      C12          O          OH          H    H4403   4-CF3O-Ph       NH      Ph           O          OH          H    H4404   4-CF3O-Ph       NH      C12          S          OH          H    H4405   4-CF3O-Ph       NH      Ph           S          OH          H    H4406   4-CF3O-Ph       NMe     H            NH         OH          H    H4407   4-CF3O-Ph       NEt     H            NH         OH          H    H4408   4-CF3O-Ph       NPr     H            NH         OH          H    H4409   4-CF3O-Ph       O       H            NH         OH          H    H4410   4-CF3O-Ph       S       H            NH         OH          H    H4411   4-CH3S-Ph        NH    H           NH    H            H         H4412   4-CH3S-Ph        NH    H           NH    OH           H         H4413   4-CH3S-Ph        NH    H           NH    OA6          H         H4414   4-CH3S-Ph        NH    H           NH    OA8          H         H4415   4-CH3S-Ph        NH    H           NH    OA9          H         H4416   4-CH3S-Ph        NH    H           NH    OA10         H         H4417   4-CH3S-Ph        NH    H           NH    OA12         H         H4418   4-CH3S-Ph        NH    H           NH    OA14         H         H4419   4-CH3S-Ph        NH    H           NH    OA16         H         H4420   4-CH3S-Ph        NH    H           NH    OH           H         A64421   4-CH3S-Ph        NH    H           NH    OH           H         A84422   4-CH3S-Ph        NH    H           NH    OH           H         A94423   4-CH3S-Ph        NH    H           NH    OH           H         A104424   4-CH3S-Ph        NH    H           NH    OH           H         A124425   4-CH3S-Ph        NH    H           NH    OH           H         A144426   4-CH3S-Ph        NH    H           NH    OH           H         A164427   4-CH3S-Ph        NH    H           NH    OH           A6        A64428   4-CH3S-Ph        NH    H           NH    OH           A8        A84429   4-CH3S-Ph        NH    H           NH    OH           A10       A104430   4-CH3S-Ph        NH    H           NH    OA2          A2        A24431   4-CH3S-Ph        NH    H           NH    OA3          A3        A34432   4-CH3S-Ph        NH    H           NH    OA4          A4        A44433   4-CH3S-Ph        NH    H           NH    OC6          H         H4434   4-CH3S-Ph        NH    H           NH    OC7          H         H4435   4-CH3S-Ph        NH    H           NH    OC8          H         H4436   4-CH3S-Ph        NH    H           NH    OC10         H         H4437   4-CH3S-Ph        NH    H           NH    OC11         H         H4438   4-CH3S-Ph        NH    H           NH    OC12         H         H4439   4-CH3S-Ph        NH    H           NH    OC14         H         H4440   4-CH3S-Ph        NH    H      NH          OC16           H    H4441   4-CH3S-Ph        NH    H      NH          C6CO3         H    H4442   4-CH3S-Ph        NH    H      NH          C7CO3         H    H4443   4-CH3S-Ph        NH    H      NH          C8CO3         H    H4444   4-CH3S-Ph        NH    H      NH          C9CO3         H    H4445   4-CH3S-Ph        NH    H      NH          C10CO3        H    H4446   4-CH3S-Ph        NH    H      NH          C12CO3        H    H4447   4-CH3S-Ph        NH    H      NH          C16CO3        H    H4448   4-CH3S-Ph        NH    C8     NH          OH             H    H4449   4-CH3S-Ph        NH    C9     NH          OH             H    H4450   4-CH3S-Ph        NH    C10    NH          OH             H    H4451   4-CH3S-Ph        NH    C12    NH          OH             H    H4452   4-CH3S-Ph        NH    C16    NH          OH             H    H4453   4-CH3S-Ph        NH    F1     NH          OH             H    H4454   4-CH3S-Ph        NH    F2     NH          OH             H    H4455   4-CH3S-Ph        NH    F3     NH          OH             H    H4456   4-CH3S-Ph        NH    F4     NH          OH             H    H4457   4-CH3S-Ph        NH    F5     NH          OH             H    H4458   4-CH3S-Ph        NH    F6     NH          OH             H    H4459   4-CH3S-Ph        NH    F7     NH          OH             H    H4460   4-CH3S-Ph        NH    F8     NH          OH             H    H4461   4-CH3S-Ph        NH    F9     NH          OH             H    H4462   4-CH3S-Ph        NH    F10    NH          OH             H    H4463   4-CH3S-Ph        NH    Ph     NH          OH             H    H4464   4-CH3S-Ph        NH    Bn     NH          OH             H    H4465   4-CH3S-Ph        NH    Pe     NH          OH             H    H4466   4-CH3S-Ph        NH    C12    NMe         OH             H    H4467   4-CH3S-Ph        NH    C12    NEt         OH             H    H4468   4-CH3S-Ph        NH    C12    NPr         OH             H    H4469  4-CH3S-Ph        NH   (CH2)3     N     OH      H         H4470  4-CH3S-Ph        NH   (CH2)4     N     OH      H         H4471  4-CH3S-Ph        NH   (CH2)5     N     OH      H         H4472  4-CH3S-Ph        NH   C12           O     OH      H         H4473  4-CH3S-Ph        NH   Ph            O     OH      H         H4474  4-CH3S-Ph        NH   C12           S     OH      H         H4475  4-CH3S-Ph        NH   Ph            S     OH      H         H4476  4-CH3S-Ph        NMe  H             NH    OH      H         H4477  4-CH3S-Ph        NEt  H             NH    OH      H         H4478  4-CH3S-Ph        NPr  H             NH    OH      H         H4479  4-CH3S-Ph        O    H             NH    OH      H         H4480  4-CH3S-Ph        S    H             NH    OH      H         H4481  4-CF3S-Ph        NH   H             NH    H       H         H4482  4-CF3S-Ph        NH   H             NH    OH      H         H4483  4-CF3S-Ph        NH   H             NH    OA6     H         H4484  4-CF3S-Ph        NH   H             NH    OA8     H         H4485  4-CF3S-Ph        NH   H             NH    OA9     H         H4486  4-CF3S-Ph        NH   H             NH    OA10    H         H4487  4-CF3S-Ph        NH   H             NH    OA12    H         H4488  4-CF3S-Ph        NH   H             NH    OA14    H         H4489  4-CF3S-Ph        NH   H             NH    OA16    H         H4490  4-CF3S-Ph        NH   H             NH    OH      H         A64491  4-CF3S-Ph        NH   H             NH    OH      H         A84492  4-CF3S-Ph        NH   H             NH    OH      H         A94493  4-CF3S-Ph        NH   H             NH    OH      H         A104494  4-CF3S-Ph        NH   H             NH    OH      H         A124495  4-CF3S-Ph        NH   H             NH    OH      H         A144496  4-CF3S-Ph        NH   H             NH    OH      H         A164497  4-CF3S-Ph        NH   H             NH    OH      A6        A64498   4-CF3S-Ph       NH   H       NH          OH             A8   A84499   4-CF3S-Ph       NH   H       NH          OH             A10  A104500   4-CF3S-Ph       NH   H       NH          OA2            A2   A24501   4-CF3S-Ph       NH   H       NH          OA3            A3   A34502   4-CF3S-Ph       NH   H       NH          OA4            A4   A44503   4-CF3S-Ph       NH   H       NH          OC6            H    H4504   4-CF3S-Ph       NH   H       NH          OC7            H    H4505   4-CF3S-Ph       NH   H       NH          OC8            H    H4506   4-CF3S-Ph       NH   H       NH          OC10           H    H4507   4-CF3S-Ph       NH   H       NH          OC11           H    H4508   4-CF3S-Ph       NH   H       NH          OC12           H    H4509   4-CF3S-Ph       NH   H       NH          OC14           H    H4510   4-CF3S-Ph       NH   H       NH          OC16           H    H4511   4-CF3S-Ph       NH   H       NH          C6CO3         H    H4512   4-CF3S-Ph       NH   H       NH          C7CO3         H    H4513   4-CF3S-Ph       NH   H       NH          C8CO3         H    H4514   4-CF3S-Ph       NH   H       NH          C9CO3         H    H4515   4-CF3S-Ph       NH   H       NH          C10CO3        H    H4516   4-CF3S-Ph       NH   H       NH          C12CO3        H    H4517   4-CF3S-Ph       NH   H       NH          C16CO3        H    H4518   4-CF3S-Ph       NH   C8      NH          OH             H    H4519   4-CF3S-Ph       NH   C9      NH          OH             H    H4520   4-CF3S-Ph       NH   C10     NH          OH             H    H4521   4-CF3S-Ph       NH   C12     NH          OH             H    H4522   4-CF3S-Ph       NH   C16     NH          OH             H    H4523   4-CF3S-Ph       NH   F1      NH          OH             H    H4524   4-CF3S-Ph       NH   F2      NH          OH             H    H4525   4-CF3S-Ph       NH   F3      NH          OH             H    H4526   4-CF3S-Ph       NH   F4      NH          OH             H    H4527   4-CF3S-Ph       NH           F5             NH           OH     H    H4528   4-CF3S-Ph       NH           F6             NH           OH     H    H4529   4-CF3S-Ph       NH           F7             NH           OH     H    H4530   4-CF3S-Ph       NH           F8             NH           OH     H    H4531   4-CF3S-Ph       NH           F9             NH           OH     H    H4532   4-CF3S-Ph       NH           F10            NH           OH     H    H4533   4-CF3S-Ph       NH           Ph             NH           OH     H    H4534   4-CF3S-Ph       NH           Bn             NH           OH     H    H4535   4-CF3S-Ph       NH           Pe             NH           OH     H    H4536   4-CF3S-Ph       NH           C12            NMe          OH     H    H4537   4-CF3S-Ph       NH           C12            NEt          OH     H    H4538   4-CF3S-Ph       NH           C12            NPr          OH     H    H4539   4-CF3S-Ph       NH           (CH2)3      N            OH     H    H4540   4-CF3S-Ph       NH           (CH2)4      N            OH     H    H4541   4-CF3S-Ph       NH           (CH2)5      N            OH     H    H4542   4-CF3S-Ph       NH           C12            O            OH     H    H4543   4-CF3S-Ph       NH           Ph             O            OH     H    H4544   4-CF3S-Ph       NH           C12            S            OH     H    H4545   4-CF3S-Ph       NH           Ph             S            OH     H    H4546   4-CF3S-Ph       NMe          H              NH           OH     H    H4547   4-CF3S-Ph       NEt          H              NH           OH     H    H4548   4-CF3S-Ph       NPr          H              NH           OH     H    H4549   4-CF3S-Ph       O            H              NH           OH     H    H4550   4-CF3S-Ph       S            H              NH           OH     H    H4551   3-CH3S-Ph       NH           H              NH           H      H    H4552   3-CH3S-Ph       NH           H              NH           OH     H    H4553   3-CH3S-Ph       NH           H              NH           OA6    H    H4554   3-CH3S-Ph       NH           H              NH           OA8    H    H4555   3-CH3S-Ph       NH           H              NH           OA9    H    H4556   3-CH3S-Ph        NH      H     NH       OA10        H        H4557   3-CH3S-Ph        NH      H     NH       OA12        H        H4558   3-CH3S-Ph        NH      H     NH       OA14        H        H4559   3-CH3S-Ph        NH      H     NH       OA16        H        H4560   3-CH3S-Ph        NH      H     NH       OH          H        A64561   3-CH3S-Ph        NH      H     NH       OH          H        A84562   3-CH3S-Ph        NH      H     NH       OH          H        A94563   3-CH3S-Ph        NH      H     NH       OH          H        A104564   3-CH3S-Ph        NH      H     NH       OH          H        A124565   3-CH3S-Ph        NH      H     NH       OH          H        A144566   3-CH3S-Ph        NH      H     NH       OH          H        A164567   3-CH3S-Ph        NH      H     NH       OH          A6       A64568   3-CH3S-Ph        NH      H     NH       OH          A8       A84569   3-CH3S-Ph        NH      H     NH       OH          A10      A104570   3-CH3S-Ph        NH      H     NH       OA2         A2       A24571   3-CH3S-Ph        NH      H     NH       OA3         A3       A34572   3-CH3S-Ph        NH      H     NH       OA4         A4       A44573   3-CH3S-Ph        NH      H     NH       OC6         H        H4574   3-CH3S-Ph        NH      H     NH       OC7         H        H4575   3-CH3S-Ph        NH      H     NH       OC8         H        H4576   3-CH3S-Ph        NH      H     NH       OC10        H        H4577   3-CH3S-Ph        NH      H     NH       OC11        H        H4578   3-CH3S-Ph        NH      H     NH       OC12        H        H4579   3-CH3S-Ph        NH      H     NH       OC14        H        H4580   3-CH3S-Ph        NH      H     NH       OC16        H        H4581   3-CH3S-Ph        NH      H     NH       C6CO3      H        H4582   3-CH3S-Ph        NH      H     NH       C7CO3      H        H4583   3-CH3S-Ph        NH      H     NH       C8CO3      H        H4584   3-CH3S-Ph        NH      H     NH       C9CO3      H        H4585  3-CH3S-Ph         NH    H              NH    C10CO3     H     H4586  3-CH3S-Ph         NH    H              NH    C12CO3     H     H4587  3-CH3S-Ph         NH    H              NH    C16CO3     H     H4588  3-CH3S-Ph         NH    C8             NH    OH          H     H4589  3-CH3S-Ph         NH    C9             NH    OH          H     H4590  3-CH3S-Ph         NH    C10            NH    OH          H     H4591  3-CH3S-Ph         NH    C12            NH    OH          H     H4592  3-CH3S-Ph         NH    C16            NH    OH          H     H4593  3-CH3S-Ph         NH    F1             NH    OH          H     H4594  3-CH3S-Ph         NH    F2             NH    OH          H     H4595  3-CH3S-Ph         NH    F3             NH    OH          H     H4596  3-CH3S-Ph         NH    F4             NH    OH          H     H4597  3-CH3S-Ph         NH    F5             NH    OH          H     H4598  3-CH3S-Ph         NH    F6             NH    OH          H     H4599  3-CH3S-Ph         NH    F7             NH    OH          H     H4600  3-CH3S-Ph         NH    F8             NH    OH          H     H4601  3-CH3S-Ph         NH    F9             NH    OH          H     H4602  3-CH3S-Ph         NH    F10            NH    OH          H     H4603  3-CH3S-Ph         NH    Ph             NH    OH          H     H4604  3-CH3S-Ph         NH    Bn             NH    OH          H     H4605  3-CH3S-Ph         NH    Pe             NH    OH          H     H4606  3-CH3S-Ph         NH    C12            NMe   OH          H     H4607  3-CH3S-Ph         NH    C12            NEt   OH          H     H4608  3-CH3S-Ph         NH    C12            NPr   OH          H     H4609  3-CH3S-Ph         NH    (CH2)3      N     OH          H     H4610  3-CH3S-Ph         NH    (CH2)4      N     OH          H     H4611  3-CH3S-Ph         NH    (CH2)5      N     OH          H     H4612  3-CH3S-Ph         NH    C12            O     OH          H     H4613  3-CH3S-Ph         NH    Ph             O     OH          H     H4614   3-CH3S-Ph      NH      C12      S          OH      H          H4615   3-CH3S-Ph      NH      Ph       S          OH      H          H4616   3-CH3S-Ph      NMe     H        NH         OH      H          H4617   3-CH3S-Ph      NEt     H        NH         OH      H          H4618   3-CH3S-Ph      NPr     H        NH         OH      H          H4619   3-CH3S-Ph      O       H        NH         OH      H          H4620   3-CH3S-Ph      S       H        NH         OH      H          H4621   3-F-4-Me-Ph     NH      H        NH         H       H          H4622   3-F-4-Me-Ph     NH      H        NH         OH      H          H4623   3-F-4-Me-Ph     NH      H        NH         OA6     H          H4624   3-F-4-Me-Ph     NH      H        NH         OA8     H          H4625   3-F-4-Me-Ph     NH      H        NH         OA9     H          H4626   3-F-4-Me-Ph     NH      H        NH         OA10    H          H4627   3-F-4-Me-Ph     NH      H        NH         OA12    H          H4628   3-F-4-Me-Ph     NH      H        NH         OA14    H          H4629   3-F-4-Me-Ph     NH      H        NH         OA16    H          H4630   3-F-4-Me-Ph     NH      H        NH         OH      H          A64631   3-F-4-Me-Ph     NH      H        NH         OH      H          A84632   3-F-4-Me-Ph     NH      H        NH         OH      H          A94633   3-F-4-Me-Ph     NH      H        NH         OH      H          A104634   3-F-4-Me-Ph     NH      H        NH         OH      H          A124635   3-F-4-Me-Ph     NH      H        NH         OH      H          A144636   3-F-4-Me-Ph     NH      H        NH         OH      H          A164637   3-F-4-Me-Ph     NH      H        NH         OH      A6         A64638   3-F-4-Me-Ph     NH      H        NH         OH      A8         A84639   3-F-4-Me-Ph     NH      H        NH         OH      A10        A104640   3-F-4-Me-Ph     NH      H        NH         OA2     A2         A24641   3-F-4-Me-Ph     NH      H        NH         OA3     A3         A34642   3-F-4-Me-Ph     NH      H       NH          OA4     A4         A44643   3-F-4-Me-Ph      NH   H      NH           OC6             H    H4644   3-F-4-Me-Ph      NH   H      NH           OC7             H    H4645   3-F-4-Me-Ph      NH   H      NH           OC8             H    H4646   3-F-4-Me-Ph      NH   H      NH           OC10            H    H4647   3-F-4-Me-Ph      NH   H      NH           OC11            H    H4648   3-F-4-Me-Ph      NH   H      NH           OC12            H    H4649   3-F-4-Me-Ph      NH   H      NH           OC14            H    H4650   3-F-4-Me-Ph      NH   H      NH           OC16            H    H4651   3-F-4-Me-Ph      NH   H      NH           C6CO3          H    H4652   3-F-4-Me-Ph      NH   H      NH           C7CO3          H    H4653   3-F-4-Me-Ph      NH   H      NH           C8CO3          H    H4654   3-F-4-Me-Ph      NH   H      NH           C9CO3          H    H4655   3-F-4-Me-Ph      NH   H      NH           C10CO3         H    H4656   3-F-4-Me-Ph      NH   H      NH           C12CO3         H    H4657   3-F-4-Me-Ph      NH   H      NH           C16CO3         H    H4658   3-F-4-Me-Ph      NH   C8     NH           OH              H    H4659   3-F-4-Me-Ph      NH   C9     NH           OH              H    H4660   3-F-4-Me-Ph      NH   C10    NH           OH              H    H4661   3-F-4-Me-Ph      NH   C12    NH           OH              H    H4662   3-F-4-Me-Ph      NH   C16    NH           OH              H    H4663   3-F-4-Me-Ph      NH   F1     NH           OH              H    H4664   3-F-4-Me-Ph      NH   F2     NH           OH              H    H4665   3-F-4-Me-Ph      NH   F3     NH           OH              H    H4666   3-F-4-Me-Ph      NH   F4     NH           OH              H    H4667   3-F-4-Me-Ph      NH   F5     NH           OH              H    H4668   3-F-4-Me-Ph      NH   F6     NH           OH              H    H4669   3-F-4-Me-Ph      NH   F7     NH           OH              H    H4670   3-F-4-Me-Ph      NH   F8     NH           OH              H    H4671   3-F-4-Me-Ph      NH   F9     NH           OH              H    H4672   3-F-4-Me-Ph      NH   F10          NH   OH           H    H4673   3-F-4-Me-Ph      NH   Ph           NH   OH           H    H4674   3-F-4-Me-Ph      NH   Bn           NH   OH           H    H4675   3-F-4-Me-Ph      NH   Pe           NH   OH           H    H4676   3-F-4-Me-Ph      NH   C12          NMe  OH           H    H4677   3-F-4-Me-Ph      NH   C12          NEt  OH           H    H4678   3-F-4-Me-Ph      NH   C12          NPr  OH           H    H4679   3-F-4-Me-Ph      NH   (CH2)3    N    OH           H    H4680   3-F-4-Me-Ph      NH   (CH2)4    N    OH           H    H4681   3-F-4-Me-Ph      NH   (CH2)5    N    OH           H    H4682   3-F-4-Me-Ph      NH   C12          O    OH           H    H4683   3-F-4-Me-Ph      NH   Ph           O    OH           H    H4684   3-F-4-Me-Ph      NH   C12          S    OH           H    H4685   3-F-4-Me-Ph      NH   Ph           S    OH           H    H4686   3-F-4-Me-Ph      NMe  H            NH   OH           H    H4687   3-F-4-Me-Ph      NEt  H            NH   OH           H    H4688   3-F-4-Me-Ph      NPr  H            NH   OH           H    H4689   3-F-4-Me-Ph      O    H            NH   OH           H    H4690   3-F-4-Me-Ph      S    H            NH   OH           H    H4691   3-Cl-4-Me-Ph     NH   H            NH   H            H    H4692   3-Cl-4-Me-Ph     NH   H            NH   OH           H    H4693   3-Cl-4-Me-Ph     NH   H            NH   OA6          H    H4694   3-Cl-4-Me-Ph     NH   H            NH   OA8          H    H4695   3-Cl-4-Me-Ph     NH   H            NH   OA9          H    H4696   3-Cl-4-Me-Ph     NH   H            NH   OA10         H    H4697   3-Cl-4-Me-Ph     NH   H            NH   OA12         H    H4698   3-Cl-4-Me-Ph     NH   H            NH   OA14         H    H4699   3-Cl-4-Me-Ph     NH   H            NH   OA16         H    H4700   3-Cl-4-Me-Ph     NH   H            NH   OH           H    A64701   3-Cl-4-Me-Ph    NH   H     NH          OH             H      A84702   3-Cl-4-Me-Ph    NH   H     NH          OH             H      A94703   3-Cl-4-Me-Ph    NH   H     NH          OH             H      A104704   3-Cl-4-Me-Ph    NH   H     NH          OH             H      A124705   3-Cl-4-Me-Ph    NH   H     NH          OH             H      A144706   3-Cl-4-Me-Ph    NH   H     NH          OH             H      A164707   3-Cl-4-Me-Ph    NH   H     NH          OH             A6     A64708   3-Cl-4-Me-Ph    NH   H     NH          OH             A8     A84709   3-Cl-4-Me-Ph    NH   H     NH          OH             A10    A104710   3-Cl-4-Me-Ph    NH   H     NH          OA2            A2     A24711   3-Cl-4-Me-Ph    NH   H     NH          OA3            A3     A34712   3-Cl-4-Me-Ph    NH   H     NH          OA4            A4     A44713   3-Cl-4-Me-Ph    NH   H     NH          OC6            H      H4714   3-Cl-4-Me-Ph    NH   H     NH          OC7            H      H4715   3-Cl-4-Me-Ph    NH   H     NH          OC8            H      H4716   3-Cl-4-Me-Ph    NH   H     NH          OC10           H      H4717   3-Cl-4-Me-Ph    NH   H     NH          OC11           H      H4718   3-Cl-4-Me-Ph    NH   H     NH          OC12           H      H4719   3-Cl-4-Me-Ph    NH   H     NH          OC14           H      H4720   3-Cl-4-Me-Ph    NH   H     NH          OC16           H      H4721   3-Cl-4-Me-Ph    NH   H     NH          C6CO3         H      H4722   3-Cl-4-Me-Ph    NH   H     NH          C7CO3         H      H4723   3-Cl-4-Me-Ph    NH   H     NH          C8CO3         H      H4724   3-Cl-4-Me-Ph    NH   H     NH          C9CO3         H      H4725   3-Cl-4-Me-Ph    NH   H     NH          C10CO3        H      H4726   3-Cl-4-Me-Ph    NH   H     NH          C12CO3        H      H4727   3-Cl-4-Me-Ph    NH   H     NH          C16CO3        H      H4728   3-Cl-4-Me-Ph    NH   C8    NH          OH             H      H4729   3-Cl-4-Me-Ph    NH   C9    NH          OH             H      H4730   3-Cl-4-Me-Ph    NH          C10          NH      OH     H    H4731   3-Cl-4-Me-Ph    NH          C12          NH      OH     H    H4732   3-Cl-4-Me-Ph    NH          C16          NH      OH     H    H4733   3-Cl-4-Me-Ph    NH          F1           NH      OH     H    H4734   3-Cl-4-Me-Ph    NH          F2           NH      OH     H    H4735   3-Cl-4-Me-Ph    NH          F3           NH      OH     H    H4736   3-Cl-4-Me-Ph    NH          F4           NH      OH     H    H4737   3-Cl-4-Me-Ph    NH          F5           NH      OH     H    H4738   3-Cl-4-Me-Ph    NH          F6           NH      OH     H    H4739   3-Cl-4-Me-Ph    NH          F7           NH      OH     H    H4740   3-Cl-4-Me-Ph    NH          F8           NH      OH     H    H4741   3-Cl-4-Me-Ph    NH          F9           NH      OH     H    H4742   3-Cl-4-Me-Ph    NH          F10          NH      OH     H    H4743   3-Cl-4-Me-Ph    NH          Ph           NH      OH     H    H4744   3-Cl-4-Me-Ph    NH          Bn           NH      OH     H    H4745   3-Cl-4-Me-Ph    NH          Pe           NH      OH     H    H4746   3-Cl-4-Me-Ph    NH          C12          NMe     OH     H    H4747   3-Cl-4-Me-Ph    NH          C12          NEt     OH     H    H4748   3-Cl-4-Me-Ph    NH          C12          NPr     OH     H    H4749   3-Cl-4-Me-Ph    NH          (CH2)3    N       OH     H    H4750   3-Cl-4-Me-Ph    NH          (CH2)4    N       OH     H    H4751   3-Cl-4-Me-Ph    NH          (CH2)5    N       OH     H    H4752   3-Cl-4-Me-Ph    NH          C12          O       OH     H    H4753   3-Cl-4-Me-Ph    NH          Ph           O       OH     H    H4754   3-Cl-4-Me-Ph    NH          C12          S       OH     H    H4755   3-Cl-4-Me-Ph    NH          Ph           S       OH     H    H4756   3-Cl-4-Me-Ph    NMe         H            NH      OH     H    H4757   3-Cl-4-Me-Ph    NEt         H            NH      OH     H    H4758   3-Cl-4-Me-Ph    NPr         H            NH      OH     H    H4759   3-Cl-4-Me-Ph     O    H     NH        OH           H    H4760   3-Cl-4-Me-Ph     S    H     NH        OH           H    H4761   3-Me-4-Br-Ph     NH   H     NH        H            H    H4762   3-Me-4-Br-Ph     NH   H     NH        OH           H    H4763   3-Me-4-Br-Ph     NH   H     NH        OA6          H    H4764   3-Me-4-Br-Ph     NH   H     NH        OA8          H    H4765   3-Me-4-Br-Ph     NH   H     NH        OA9          H    H4766   3-Me-4-Br-Ph     NH   H     NH        OA10         H    H4767   3-Me-4-Br-Ph     NH   H     NH        OA12         H    H4768   3-Me-4-Br-Ph     NH   H     NH        OA14         H    H4769   3-Me-4-Br-Ph     NH   H     NH        OA16         H    H4770   3-Me-4-Br-Ph     NH   H     NH        OH           H    A64771   3-Me-4-Br-Ph     NH   H     NH        OH           H    A84772   3-Me-4-Br-Ph     NH   H     NH        OH           H    A94773   3-Me-4-Br-Ph     NH   H     NH        OH           H    A104774   3-Me-4-Br-Ph     NH   H     NH        OH           H    A124775   3-Me-4-Br-Ph     NH   H     NH        OH           H    A144776   3-Me-4-Br-Ph     NH   H     NH        OH           H    A164777   3-Me-4-Br-Ph     NH   H     NH        OH           A6   A64778   3-Me-4-Br-Ph     NH   H     NH        OH           A8   A84779   3-Me-4-Br-Ph     NH   H     NH        OH           A10  A104780   3-Me-4-Br-Ph     NH   H     NH        OA2          A2   A24781   3-Me-4-Br-Ph     NH   H     NH        OA3          A3   A34782   3-Me-4-Br-Ph     NH   H     NH        OA4          A4   A44783   3-Me-4-Br-Ph     NH   H     NH        OC6          H    H4784   3-Me-4-Br-Ph     NH   H     NH        OC7          H    H4785   3-Me-4-Br-Ph     NH   H     NH        OC8          H    H4786   3-Me-4-Br-Ph     NH   H     NH        OC10         H    H4787   3-Me-4-Br-Ph     NH   H     NH        OC11         H    H4788   3-Me-4-Br-Ph     NH   H            NH   OC12         H   H4789   3-Me-4-Br-Ph     NH   H            NH   OC14         H   H4790   3-Me-4-Br-Ph     NH   H            NH   OC16         H   H4791   3-Me-4-Br-Ph     NH   H            NH   C6CO3       H   H4792   3-Me-4-Br-Ph     NH   H            NH   C7CO3       H   H4793   3-Me-4-Br-Ph     NH   H            NH   C8CO3       H   H4794   3-Me-4-Br-Ph     NH   H            NH   C9CO3       H   H4795   3-Me-4-Br-Ph     NH   H            NH   C10CO3      H   H4796   3-Me-4-Br-Ph     NH   H            NH   C12CO3      H   H4797   3-Me-4-Br-Ph     NH   H            NH   C16CO3      H   H4798   3-Me-4-Br-Ph     NH   C8           NH   OH           H   H4799   3-Me-4-Br-Ph     NH   C9           NH   OH           H   H4800   3-Me-4-Br-Ph     NH   C10          NH   OH           H   H4801   3-Me-4-Br-Ph     NH   C12          NH   OH           H   H4802   3-Me-4-Br-Ph     NH   C16          NH   OH           H   H4803   3-Me-4-Br-Ph     NH   F1           NH   OH           H   H4804   3-Me-4-Br-Ph     NH   F2           NH   OH           H   H4805   3-Me-4-Br-Ph     NH   F3           NH   OH           H   H4806   3-Me-4-Br-Ph     NH   F4           NH   OH           H   H4807   3-Me-4-Br-Ph     NH   F5           NH   OH           H   H4808   3-Me-4-Br-Ph     NH   F6           NH   OH           H   H4809   3-Me-4-Br-Ph     NH   F7           NH   OH           H   H4810   3-Me-4-Br-Ph     NH   F8           NH   OH           H   H4811   3-Me-4-Br-Ph     NH   F9           NH   OH           H   H4812   3-Me-4-Br-Ph     NH   F10          NH   OH           H   H4813   3-Me-4-Br-Ph     NH   Ph           NH   OH           H   H4814   3-Me-4-Br-Ph     NH   Bn           NH   OH           H   H4815   3-Me-4-Br-Ph     NH   Pe           NH   OH           H   H4816   3-Me-4-Br-Ph     NH   C12          NMe  OH           H   H4817   3-Me-4-Br-Ph         NH   C12         NEt  OH         H   H4818   3-Me-4-Br-Ph         NH   C12         NPr  OH         H   H4819   3-Me-4-Br-Ph         NH   (CH2)3   N    OH         H   H4820   3-Me-4-Br-Ph         NH   (CH2)4   N    OH         H   H4821   3-Me-4-Br-Ph         NH   (CH2)5   N    OH         H   H4822   3-Me-4-Br-Ph         NH   C12         O    OH         H   H4823   3-Me-4-Br-Ph         NH   Ph          O    OH         H   H4824   3-Me-4-Br-Ph         NH   C12         S    OH         H   H4825   3-Me-4-Br-Ph         NH   Ph          S    OH         H   H4826   3-Me-4-Br-Ph         NMe  H           NH   OH         H   H4827   3-Me-4-Br-Ph         NEt  H           NH   OH         H   H4828   3-Me-4-Br-Ph         NPr  H           NH   OH         H   H4829   3-Me-4-Br-Ph         O    H           NH   OH         H   H4830   3-Me-4-Br-Ph         S    H           NH   OH         H   H4831   3-NO2-4-F-Ph        NH   H           NH   H          H   H4832   3-NO2-4-F-Ph        NH   H           NH   OH         H   H4833   3-NO2-4-F-Ph        NH   H           NH   OA6        H   H4834   3-NO2-4-F-Ph        NH   H           NH   OA8        H   H4835   3-NO2-4-F-Ph        NH   H           NH   OA9        H   H4836   3-NO2-4-F-Ph        NH   H           NH   OA10       H   H4837   3-NO2-4-F-Ph        NH   H           NH   OA12       H   H4838   3-NO2-4-F-Ph        NH   H           NH   OA14       H   H4839   3-NO2-4-F-Ph        NH   H           NH   OA16       H   H4840   3-NO2-4-F-Ph        NH   H           NH   OH         H   A64841   3-NO2-4-F-Ph        NH   H           NH   OH         H   A84842   3-NO2-4-F-Ph        NH   H           NH   OH         H   A94843   3-NO2-4-F-Ph        NH   H           NH   OH         H   A104844   3-NO2-4-F-Ph        NH   H           NH   OH         H   A124845   3-NO2-4-F-Ph        NH   H           NH   OH         H   A144846      3-NO2-4-F-Ph         NH           H           NH         OH          H        A164847      3-NO2-4-F-Ph         NH           H           NH         OH          A6       A64848      3-MO2-4-F-Ph         NH           H           NH         OH          A8       A84849      3-NO2-4-F-Ph         NH           H           NH         OH          A10      A104850      3-NO2-4-F-Ph         NH           H           NH         OA2         A2       A24851      3-NO2-4-F-Ph         NH           H           NH         OA3         A3       A34852      3-NO2-4-F-Ph         NH           H           NH         OA4         A4       A44853      3-NO2-4-F-Ph         NH           H           NH         OC6         H        H4854      3-NO2-4-F-Ph         NH           H           NH         OC7         H        H4855      3-NO2-4-F-Ph         NH           H           NH         OC8         H        H4856      3-NO2-4-F-Ph         NH           H           NH         OC10        H        H4857      3-NO2-4-F-Ph         NH           H           NH         OC11        H        H4858      3-NO2-4-F-Ph         NH           H           NH         OC12        H        H4859      3-NO2-4-F-Ph         NH           H           NH         OC14        H        H4860      3-NO2-4-F-Ph         NH           H           NH         OC16        H        H4861      3-NO2-4-F-Ph         NH           H           NH         C6CO3      H        H4862      3-NO2-4-F-Ph         NH           H           NH         C7CO3      H        H4863      3-NO2-4-F-Ph         NH           H           NH         C8CO3      H        H4864      3-NO2-4-F-Ph         NH           H           NH         C9CO3      H        H4865      3-NO2-4-F-Ph         NH           H           NH         C10CO3     H        H4866      3-NO2-4-F-Ph         NH           H           NH         C12CO3     H        H4867      3-NO2-4-F-Ph         NH           H           NH         C16CO3     H        H4868      3-NO2-4-F-Ph         NH           C8          NH         OH          H        H4869      3-NO2-4-F-Ph         NH           C9          NH         OH          H        H4870      3-NO2-4-F-Ph         NH           C10         NH         OH          H        H4871      3-NO2-4-F-Ph         NH           C12         NH         OH          H        H4872      3-NO2-4-F-Ph         NH           C16         NH         OH          H        H4873      3-NO2-4-F-Ph         NH           F1          NH         OH          H        H4874      3-NO2-4-F-Ph         NH           F2          NH         OH          H        H4875      3-NO2-4-F-Ph         NH           F3          NH         OH          H        H4876      3-NO2-4-F-Ph         NH           F4          NH         OH          H        H4877      3-NO2-4-F-Ph         NH           F5          NH         OH          H        H4878      3-NO2-4-F-Ph         NH           F6          NH         OH          H        H4879      3-NO2-4-F-Ph         NH           F7          NH         OH          H        H4880      3-NO2-4-F-Ph         NH           F8          NH         OH          H        H4881      3-NO2-4-F-Ph         NH           F9          NH         OH          H        H4882      3-NO2-4-F-Ph         NH           F10         NH         OH          H        H4883      3-NO2-4-F-Ph         NH           Ph          NH         OH          H        H4884      3-NO2-4-F-Ph         NH           Bn          NH         OH          H        H4885      3-NO2-4-F-Ph         NH           Pe          NH         OH          H        H4886      3-NO2-4-F-Ph         NH           C12         NMe        OH          H        H4887      3-NO2-4-F-Ph         NH           C12         NEt        OH          H        H4888      3-NO2-4-F-Ph         NH           C12         NPr        OH          H        H4889      3-NO2-4-F-Ph         NH           (CH2)3   N          OH          H        H4890      3-NO2-4-F-Ph         NH           (CH2)4   N          OH          H        H4891      3-NO2-4-F-Ph         NH           (CH2)5   N          OH          H        H4892      3-NO2-4-F-Ph         NH           C12         O          OH          H        H4893      3-NO2-4-F-Ph         NH           Ph          O          OH          H        H4894      3-NO2-4-F-Ph         NH           C12         S          OH          H        H4895      3-NO2-4-F-Ph         NH           Ph          S          OH          H        H4896      3-NO2-4-F-Ph         NMe          H           NH         OH          H        H4897      3-NO2-4-F-Ph         NEt          H           NH         OH          H        H4898      3-NO2-4-F-Ph         NPr          H           NH         OH          H        H4899      3-NO2-4-F-Ph         O            H           NH         OH          H        H4900      3-NO2-4-F-Ph         S            H           NH         OH          H        H4901      3-NO2-4-Cl-Ph        NH           H           NH         H           H        H4902      3-NO2-4-Cl-Ph        NH           H           NH         OH          H        H4903      3-NO2-4-Cl-Ph        NH           H           NH         OA6         H        H4904      3-NO2-4-Cl-Ph        NH           H           NH         OA8         H        H4905      3-NO2-4-Cl-Ph        NH           H           NH         OA9         H        H4906      3-NO2-4-Cl-Ph        NH           H           NNH        OM10        H        H4907      3-NO2-4-Cl-Ph        NH           H           NH         OA12        H        H4908      3-NO2-4-Cl-Ph        NH           H           NH         OA14        H        H4909      3-NO2-4-Cl-Ph        NH           H           NH         OA16        H        H4910      3-NO2-4-Cl-Ph        NH           H           NH         OH          H        A64911      3-NO2-4-Cl-Ph        NH           H           NH         OH          H        A84912      3-NO2-4-Cl-Ph        NH           H           NH         OH          H        A94913      3-NO2-4-Cl-Ph        NH           H           NH         OH          H        A104914      3-NO2-4-Cl-Ph        NH           H           NH         OH          H        A124915      3-NO2-4-Cl-Ph        NH           H           NH         OH          H        A144916      3-NO2-4-Cl-Ph        NH           H           NH         OH          H        A164917      3-NO2-4-Cl-Ph        NH           H           NH         OH          A6       A64918      3-NO2-4-Cl-Ph        NH           H           NH         OH          A8       A84919      3-NO2-4-Cl-Ph        NH           H           NH         OH          A10      A104920      3-NO2-4-Cl-Ph        NH           H           NH         OA2         A2       A24921      3-NO2-4-Cl-Ph        NH           H           NH         OA3         A3       A34922      3-NO2-4-Cl-Ph        NH           H           NH         OA4         A4       A44923      3-NO2-4-Cl-Ph        NH           H           NH         OC6         H        H4924      3-NO2-4-Cl-Ph        NH           H           NH         OC7         H        H4925      3-NO2-4-Cl-Ph        NH           H           NH         OC8         H        H4926      3-NO2-4-Cl-Ph        NH           H           NH         OC10        H        H4927      3-NO2-4-Cl-Ph        NH           H           NH         OC11        H        H4928      3-NO2-4-Cl-Ph        NH           H           NH         OC12        H        H4929      3-NO2-4-Cl-Ph        NH           H           NH         OC14        H        H4930      3-NO2-4-Cl-Ph        NH           H           NH         OC16        H        H4931      3-NO2-4-Cl-Ph        NH           H           NH         C6CO3      H        H4932      3-NO2-4-Cl-Ph        NH           H           NH         C7CO3      H        H4933      3-NO2-4-Cl-Ph        NH           H           NH         C8CO3      H        H4934      3-NO2-4-Cl-Ph        NH           H           NH         C9CO3      H        H4935      3-NO2-4-Cl-Ph        NH           H           NH         C10CO3     H        H4936      3-NO2-4-Cl-Ph        NH           H           NH         C12CO3     H        H4937      3-NO2-4-Cl-Ph        NH           H           NH         C16CO3     H        H4938      3-NO2-4-Cl-Ph        NH           C8          NH         OH          H        H4939      3-NO2-4-Cl-Ph        NH           C9          NH         OH          H        H4940      3-NO2-4-Cl-Ph        NH           C10         NH         OH          H        H4941      3-NO2-4-Cl-Ph        NH           C12         NH         OH          H        H4942      3-NO2-4-Cl-Ph        NH           C16         NH         OH          H        H4943      3-NO2-4-Cl-Ph        NH           F1          NH         OH          H        H4944      3-NO2-4-Cl-Ph        NH           F2          NH         OH          H        H4945      3-NO2-4-Cl-Ph        NH           F3          NH         OH          H        H4946      3-NO2-4-Cl-Ph        NH           F4          NH         OH          H        H4947      3-NO2-4-Cl-Ph        NH           F5          NH         OH          H        H4948      3-NO2-4-Cl-Ph        NH           F6          NH         OH          H        H4949      3-NO2-4-Cl-Ph        NH           F7          NH         OH          H        H4950      3-NO2-4-Cl-Ph        NH           F8          NH         OH          H        H4951      3-NO2-4-Cl-Ph        NH           F9          NH         OH          H        H4952      3-NO2-4-Cl-Ph        NH           F10         NH         OH          H        H4953      3-NO2-4-Cl-Ph        NH           Ph          NH         OH          H        H4954      3-NO2-4-Cl-Ph        NH           Bn          NH         OH          H        H4955      3-NO2-4-Cl-Ph        NH           Pe          NH         OH          H        H4956      3-NO2-4-Cl-Ph        NH           C12         NMe        OH          H        H4957      3-NO2-4-Cl-Ph        NH           C12         NEt        OH          H        H4958      3-NO2-4-Cl-Ph        NH           C12         NPr        OH          H        H4959      3-NO2-4-Cl-Ph        NH           (CH2)3   N          OH          H        H4960      3-NO2-4-Cl-Ph        NH           (CH2)4   N          OH          H        H4961      3-NO2-4-Cl-Ph        NH           (CH2)5   N          OH          H        H4962      3-NO2-4-Cl-Ph       NH           C12         O          OH          H        H4963      3-NO2-4-Cl-Ph       NH           Ph          O          OH          H        H4964      3-NO2-4-Cl-Ph       NH           C12         S          OH          H        H4965      3-NO2-4-Cl-Ph       NH           Ph          S          OH          H        H4966      3-NO2-4-Cl-Ph       NMe          H           NH         OH          H        H4967      3-NO2-4-Cl-Ph       NEt          H           NH         OH          H        H4968      3-NO2-4-Cl-Ph       NPr          H           NH         OH          H        H4969      3-NO2-4-Cl-Ph       O            H           NH         OH          H        H4970      3-NO2-4-Cl-Ph       S            H           NH         OH          H        H4971      4-(F2-O)-Ph          NH           H           NH         H           H        H4972      4-(F2-O)-Ph          NH           H           NH         OH          H        H4973      4-(F2-O)-Ph          NH           H           NH         OA6         H        H4974      4-(F2-O)-Ph          NH           H           NH         OA8         H        H4975      4-(F2-O)-Ph          NH           H           NH         OA9         H        H4976      4-(F2-O)-Ph          NH           H           NH         OA10        H        H4977      4-(F2-O)-Ph          NH           H           NH         OA12        H        H4978      4-(F2-O)-Ph          NH           H           NH         OA14        H        H4979      4-(F2-O)-Ph          NH           H           NH         OA16        H        H4980      4-(F2-O)-Ph          NH           H           NH         OH          H        A64981      4-(F2-O)-Ph          NH           H           NH         OH          H        A84982      4-(F2-O)-Ph          NH           H           NH         OH          H        A94983      4-(F2-O)-Ph          NH           H           NH         OH          H        A104984      4-(F2-O)-Ph          NH           H           NH         OH          H        A124985      4-(F2-O)-Ph          NH           H           NH         OH          H        A144986      4-(F2-O)-Ph          NH           H           NH         OH          H        A164987      4-(F2-O)-Ph          NH           H           NH         OH          A6       A64988      4-(F2-O)-Ph          NH           H           NH         OH          A8       A84989      4-(F2-O)-Ph          NH           H           NH         OH          A10      A104990      4-(F2-O)-Ph          NH           H           NH         OA2         A2       A24991      4-(F2-O)-Ph          NH           H           NH         OA3         A3       A34992      4-(F2-O)-Ph          NH           H           NH         OA4         A4       A44993      4-(F2-O)-Ph          NH           H           NH         OC6         H        H4994      4-(F2-O)-Ph          NH           H           NH         OC7         H        H4995      4-(F2-O)-Ph          NH           H           NH         OC8         H        H4996      4-(F2-O)-Ph          NH           H           NH         OC10        H        H4997      4-(F2-O)-Ph          NH           H           NH         OC11        H        H4998      4-(F2-O)-Ph          NH           H           NH         OC12        H        H4999      4-(F2-O)-Ph          NH           H           NH         OC14        H        H5000      4-(F2-O)-Ph          NH           H           NH         OC16        H        H5001      4-(F2-O)-Ph          NH           H           NH         C6CO3      H        H5002      4-(F2-O)-Ph          NH           H           NH         C7CO3      H        H5003      4-(F2-O)-Ph          NH           H           NH         C8CO3      H        H5004      4-(F2-O)-Ph          NH           H           NH         C9CO3      H        H5005      4-(F2-O)-Ph          NH           H           NH         C10CO3     H        H5006      4-(F2-O)-Ph          NH           H           NH         C12CO3     H        H5007      4-(F2-O)-Ph          NH           H           NH         C16CO3     H        H5008      4-(F2-O)-Ph          NH           C8          NH         OH          H        H5009      4-(F2-O)-Ph          NH           C9          NH         OH          H        H5010      4-(F2-O)-Ph          NH           C10         NH         OH          H        H5011      4-(F2-O)-Ph          NH           C12         NH         OH          H        H5012      4-(F2-O)-Ph          NH           C16         NH         OH          H        H5013      4-(F2-O)-Ph          NH           F1          NH         OH          H        H5014      4-(F2-O)-Ph          NH           F2          NH         OH          H        H5015      4-(F2-O)-Ph          NH           F3          NH         OH          H        H5016      4-(F2-O)-Ph          NH           F4          NH         OH          H        H5017      4-(F2-O)-Ph          NH           F5          NH         OH          H        H5018      4-(F2-O)-Ph          NH           F6          NH         OH          H        H5019      4-(F2-O)-Ph          NH           F7          NH         OH          H        H5020      4-(F2-O)-Ph          NH           F8          NH         OH          H        H5021      4-(F2-O)-Ph          NH           F9          NH         OH          H        H5022      4-(F2-O)-Ph          NH           F10         NH         OH          H        H5023      4-(F2-O)-Ph          NH           Ph          NH         OH          H        H5024      4-(F2-O)-Ph          NH           Bn          NH         OH          H        H5025      4-(F2-O)-Ph          NH           Pe          NH         OH          H        H5026      4-(F2-O)-Ph          NH           C12         NMe        OH          H        H5027      4-(F2-O)-Ph          NH           C12         NEt        OH          H        H5028      4-(F2-O)-Ph          NH           C12         NPr        OH          H        H5029      4-(F2-O)-Ph          NH           (CH2)3   N          OH          H        H5030      4-(F2-O)-Ph          NH           (CH2)4   N          OH          H        H5031      4-(F2-O)-Ph          NH           (CH2)5   N          OH          H        H5032      4-(F2-O)-Ph          NH           C12         O          OH          H        H5033      4-(F2-O)-Ph          NH           Ph          O          OH          H        H5034      4-(F2-O)-Ph          NH           C12         S          OH          H        H5035      4-(F2-O)-Ph          NH           Ph          S          OH          H        H5036      4-(F2-O)-Ph          NMe          H           NH         OH          H        H5037      4-(F2-O)-Ph          NEt          H           NH         OH          H        H5038      4-(F2-O)-Ph          NPr          H           NH         OH          H        H5039      4-(F2-O)-Ph          O            H           NH         OH          H        H5040      4-(F2-O)-Ph          S            H           NH         OH          H        H5041      4-(F3-O)-Ph          NH           H           NH         H           H        H5042      4-(F3-O)-Ph          NH           H           NH         OH          H        H5043      4-(F3-O)-Ph          NH           H           NH         OA6         H        H5044      4-(F3-O)-Ph          NH           H           NH         OA8         H        H5045      4-(F3-O)-Ph          NH           H           NH         OA9         H        H5046      4-(F3-O)-Ph          NH           H           NH         OA10        H        H5047      4-(F3-O)-Ph          NH           H           NH         OA12        H        H048      4-(F3-O)-Ph          NH           H           NH         OA14        H        H5049      4-(F3-O)-Ph          NH           H           NH         OA16        H        H5050      4-(F3-O)-Ph          NH           H           NH         OH          H        A65051      4-(F3-O)-Ph          NH           H           NH         OH          H        A85052      4-(F3-O)-Ph          NH           H           NH         OH          H        A95053      4-(F3-O)-Ph          NH           H           NH         OH          H        A105054      4-(F3-O)-Ph          NH           H           NH         OH          H        A125055      4-(F3-O)-Ph          NH           H           NH         OH          H        A145056      4-(F3-O)-Ph          NH           H           NH         OH          H        A165057      4-(F3-O)-Ph          NH           H           NH         OH          A6       A65058      4-(F3-O)-Ph          NH           H           NH         OH          A8       A85059      4-(F3-O)-Ph          NH           H           NH         OH          A10      A105060      4-(F3-O)-Ph          NH           H           NH         OA2         A2       A25061      4-(F3-O)-Ph          NH           H           NH         OA3         A3       A35062      4-(F3-O)-Ph          NH           H           NH         OA4         A4       A45063      4-(F3-O)-Ph          NH           H           NH         OC6         H        H5064      4-(F3-O)-Ph          NH           H           NH         OC7         H        H5065      4-(F3-O)-Ph          NH           H           NH         OC8         H        H5066      4-(F3-O)-Ph          NH           H           NH         OC10        H        H5067      4-(F3-O)-Ph          NH           H           NH         OC11        H        H5068      4-(F3-O)-Ph          NH           H           NH         OC12        H        H5069      4-(F3-O)-Ph          NH           H           NH         OC14        H        H5070      4-(F3-O)-Ph          NH           H           NH         OC16        H        H5071      4-(F3-O)-Ph          NH           H           NH         C6CO3      H        H5072      4-(F3-O)-Ph          NH           H           NH         C7CO3      H        H5073      4-(F3-O)-Ph          NH           H           NH         C8CO3      H        H5074      4-(F3-O)-Ph          NH           H           NH         C9CO3      H        H5075      4-(F3-O)-Ph          NH           H           NH         C10CO3     H        H5076      4-(F3-O)-Ph          NH           H           NH         C12CO3     H        H5077      4-(F3-O)-Ph          NH           H           NH         C16CO3     H        H 5078      4-(F3-O)-Ph          NH           C8          NH         OH          H        H5079      4-(F3-O)-Ph          NH           C9          NH         OH          H        H5080      4-(F3-O)-Ph          NH           C10         NH         OH          H        H5081      4-(F3-O)-Ph          NH           C12         NH         OH          H        H5082      4-(F3-O)-Ph          NH           C16         NH         OH          H        H5083      4-(F3-O)-Ph          NH           F1          NH         OH          H        H5084      4-(F3-O)-Ph          NH           F2          NH         OH          H        H5085      4-(F3-O)-Ph          NH           F3          NH         OH          H        H5086      4-(F3-O)-Ph          NH           F4          NH         OH          H        H5087      4-(F3-O)-Ph          NH           F5          NH         OH          H        H5088      4-(F3-O)-Ph          NH           F6          NH         OH          H        H5089      4-(F3-O)-Ph          NH           F7          NH         OH          H        H5090      4-(F3-O)-Ph          NH           F8          NH         OH          H        H5091      4-(F3-O)-Ph          NH           F9          NH         OH          H        H5092      4-(F3-O)-Ph          NH           F10         NH         OH          H        H5093      4-(F3-O)-Ph          NH           Ph          NH         OH          H        H5094      4-(F3-O)-Ph          NH           Bn          NH         OH          H        H5095      4-(F3-O)-Ph          NH           Pe          NH         OH          H        H5096      4-(F3-O)-Ph          NH           C12         NMe        OH          H        H5097      4-(F3-O)-Ph          NH           C12         NEt        OH          H        H5098      4-(F3-O)-Ph          NH           C12         NPr        OH          H        H5099      4-(F3-O)-Ph          NH           (CH2)3    N          OH          H        H5100      4-(F3-O)-Ph          NH           (CH2)4    N          OH          H        H5101      4-(F3-O)-Ph          NH           (CH2)5    N          OH          H        H5102      4-(F3-O)-Ph          NH           C12         O          OH          H        H5103      4-(F3-O)-Ph          NH           Ph          O          OH          H        H5104      4-(F3-O)-Ph          NH           C12         S          OH          H        H5105      4-(F3-O)-Ph          NH           Ph          S          OH          H        H5106      4-(F3-O)-Ph          NMe          H           NH         OH          H        H5107      4-(F3-O)-Ph          NEt       H         NH          OH          H         H5108      4-(F3-O)-Ph          NPr       H         NH          OH          H         H5109      4-(F3-O)-Ph          O         H         NH          OH          H         H5110      4-(F3-O)-Ph          S         H         NH          OH          H         H5111      4-(F7-O)-Ph          NH        H         NH          H           H         H5112      4-(F7-O)-Ph          NH        H         NH          OH          H         H5113      4-(F7-O)-Ph          NH        H         NH          OA6         H         H5114      4-(F7-O)-Ph          NH        H         NH          OA8         H         H5115      4-(F7-O)-Ph          NH        H         NH          OA9         H         H5116      4-(F7-O)-Ph          NH        H         NH          OA10        H         H5117      4-(F7-O)-Ph          NH        H         NH          OA12        H         H5118      4-(F7-O)-Ph          NH        H         NH          OA14        H         H5119      4-(F7-O)-Ph          NH        H         NH          OA16        H         H5120      4-(F7-O)-Ph          NH        H         NH          OH          H         A65121      4-(F7-O)-Ph          NH        H         NH          OH          H         A85122      4-(F7-O)-Ph          NH        H         NH          OH          H         A95123      4-(F7-O)-Ph          NH        H         NH          OH          H         A105124      4-(F7-O)-Ph          NH        H         NH          OH          H         A125125      4-(F7-O)-Ph          NH        H         NH          OH          H         A145126      4-(F7-O)-Ph          NH        H         NH          OH          H         A165127      4-(F7-O)-Ph          NH        H         NH          OH          A6        A65128      4-(F7-O)-Ph          NH        H         NH          OH          A8        A85129      4-(F7-O)-Ph          NH        H         NH          OH          A10       A105130      4-(F7-O)-Ph          NH        H         NH          OA2         A2        A25131      4-(F7-O)-Ph          NH        H         NH          OA3         A3        A35132      4-(F7-O)-Ph          NH        H         NH          OA4         A4        A45133      4-(F7-O)-Ph          NH        H         NH          OC6         H         H5134      4-(F7-O)-Ph          NH        H         NH          OC7         H         H5135      4-(F7-O)-Ph          NH        H         NH          OC8         H         H5136      4-(F7-O)-Ph          NH        H         NH          OC10        H         H5137      4-(F7-O)-Ph          NH        H         NH          OC11        H         H5138      4-(F7-O)-Ph          NH        H         NH          OC12        H         H5139      4-(F7-O)-Ph          NH        H         NH          OC14        H         H5140      4-(F7-O)-Ph          NH        H         NH          OC16        H         H5141      4-(F7-O)-Ph          NH        H         NH          C6CO3      H         H5142      4-(F7-O)-Ph          NH        H         NH          C7CO3      H         H5143      4-(F7-O)-Ph          NH        H         NH          C8CO3      H         H5144      4-(F7-O)-Ph          NH        H         NH          C9CO3      H         H5145      4-(F7-O)-Ph          NH        H         NH          C10CO3     H         H5146      4-(F7-O)-Ph          NH        H         NH          C12CO3     H         H5147      4-(F7-O)-Ph          NH        H         NH          C16CO3     H         H5148      4-(F7-O)-Ph          NH        C8        NH          OH          H         H5149      4-(F7-O)-Ph          NH        C9        NH          OH          H         H5150      4-(F7-O)-Ph          NH        C10       NH          OH          H         H5151      4-(F7-O)-Ph          NH        C12       NH          OH          H         H5152      4-(F7-O)-Ph          NH        C16       NH          OH          H         H5153      4-(F7-O)-Ph          NH        F1        NH          OH          H         H5154      4-(F7-O)-Ph          NH        F2        NH          OH          H         H5155      4-(F7-O)-Ph          NH        F3        NH          OH          H         H5156      4-(F7-O)-Ph          NH        F4        NH          OH          H         H5157      4-(F7-O)-Ph          NH        F5        NH          OH          H         H5158      4-(F7-O)-Ph          NH        F6        NH          OH          H         H5159      4-(F7-O)-Ph          NH        F7        NH          OH          H         H5160      4-(F7-O)-Ph          NH        F8        NH          OH          H         H5161      4-(F7-O)-Ph          NH        F9        NH          OH          H         H5162      4-(F7-O)-Ph          NH        F10       NH          OH          H         H5163      4-(F7-O)-Ph          NH        Ph        NH          OH          H         H5164      4-(F7-O)-Ph          NH        Bn        NH          OH          H         H5165      4-(F7-O)-Ph          NH        Pe        NH          OH          H         H5166      4-(F7-O)-Ph          NH        C12       NMe         OH          H         H5167      4-(F7-O)-Ph          NH        C12       NEt         OH          H         H5168      4-(F7-O)-Ph          NH        C12       NPr         OH          H         H5169      4-(F7-O)-Ph          NH        (CH2)3 N           OH          H         H5170      4-(F7-O)-Ph          NH        (CH2)4 N           OH          H         H5171      4-(F7-O)-Ph          NH        (CH2)5 N           OH          H         H5172      4-(F7-O)-Ph          NH        C12       O           OH          H         H5173      4-(F7-O)-Ph          NH        Ph        O           OH          H         H5174      4-(F7-O)-Ph          NH        C12       S           OH          H         H5175      4-(F7-O)-Ph          NH        Ph        S           OH          H         H5176      4-(F7-O)-Ph          NMe       H         NH          OH          H         H5177      4-(F7-O)-Ph          NEt       H         NH          OH          H         H5178      4-(F7-O)-Ph          NPr       H         NH          OH          H         H5179      4-(F7-O)-Ph          O         H         NH          OH          H         H5180      4-(F7-O)-Ph          S         H         NH          OH          H         H5181      4-(F8-O)-Ph          NH        H         NH          H           H         H5182      4-(F8-O)-Ph          NH        H         NH          OH          H         H5183      4-(F8-O)-Ph          NH        H         NH          OA6         H         H5184      4-(F8-O)-Ph          NH        H         NH          OA8         H         H5185      4-(F8-O)-Ph          NH        H         NH          OA9         H         H5186      4-(F8-O)-Ph          NH        H         NH          OA10        H         H5187      4-(F8-O)-Ph          NH        H         NH          OA12        H         H5188      4-(F8-O)-Ph          NH        H         NH          OA14        H         H5189      4-(F8-O)-Ph          NH        H         NH          OA16        H         H5190      4-(F8-O)-Ph          NH        H         NH          OH          H         A65191      4-(F8-O)-Ph          NH        H         NH          OH          H         A85192      4-(F8-O)-Ph          NH        H         NH          OH          H         A95193      4-(F8-O)-Ph          NH        H         NH          OH          H         A105194      4-(F8-O)-Ph          NH        H         NH          OH          H         A125195      4-(F8-O)-Ph          NH        H         NH          OH          H         A145196      4-(F8-O)-Ph          NH        H         NH          OH          H         A165197      4-(F8-O)-Ph          NH        H         NH          OH          A6        A65198      4-(F8-O)-Ph          NH        H         NH          OH          A8        A85199      4-(F8-O)-Ph          NH        H         NH          OH          A10       A105200      4-(F8-O)-Ph          NH        H         NH          OA2         A2        A25201      4-(F8-O)-Ph          NH        H         NH          OA3         A3        A35202      4-(F8-O)-Ph          NH        H         NH          OA4         A4        A45203      4-(F8-O)-Ph          NH        H         NH          OC6         H         H5204      4-(F8-O)-Ph          NH        H         NH          OC7         H         H5205      4-(F8-O)-Ph          NH        H         NH          OC8         H         H5206      4-(F8-O)-Ph          NH        H         NH          OC10        H         H5207      4-(F8-O)-Ph          NH        H         NH          OC11        H         H5208      4-(F8-O)-Ph          NH        H         NH          OC12        H         H5209      4-(F8-O)-Ph          NH        H         NH          OC14        H         H5210      4-(F8-O)-Ph          NH        H         NH          OC16        H         H5211      4-(F8-O)-Ph          NH        H         NH          C6CO3      H         H5212      4-(F8-O)-Ph          NH        H         NH          C7CO3      H         H5213      4-(F8-O)-Ph          NH        H         NH          C8CO3      H         H5214      4-(F8-O)-Ph          NH        H         NH          C9CO3      H         H5215      4-(F8-O)-Ph          NH        H         NH          C10CO3     H         H5216      4-(F8-O)-Ph          NH        H         NH          C12CO3     H         H5217      4-(F8-O)-Ph          NH        H         NH          C16CO3     H         H5218      4-(F8-O)-Ph          NH        C8        NH          OH          H         H5219      4-(F8-O)-Ph          NH        C9        NH          OH          H         H5220      4-(F8-O)-Ph          NH        C10       NH          OH          H         H5221      4-(F8-O)-Ph          NH        C12       NH          OH          H         H5222      4-(F8-O)-Ph          NH        C16       NH          OH          H         H5223      4-(F8-O)-Ph          NH        F1        NH          OH          H         H5224      4-(F8-O)-Ph          NH        F2        NH          OH          H         H5225      4-(F8-O)-Ph          NH        F3        NH          OH          H         H5226      4-(F8-O)-Ph          NH        F4        NH          OH          H         H5227      4-(F8-O)-Ph          NH        F5        NH          OH          H         H5228      4-(F8-O)-Ph          NH        F6        NH          OH          H         H5229      4-(F8-O)-Ph          NH        F7        NH          OH          H         H5230      4-(F8-O)-Ph          NH        F8        NH          OH          H         H5231      4-(F8-O)-Ph          NH        F9        NH          OH          H         H5232      4-(F8-O)-Ph          NH        F10       NH          OH          H         H5233      4-(F8-O)-Ph          NH        Ph        NH          OH          H         H5234      4-(F8-O)-Ph          NH        Bn        NH          OH          H         H45235      4-(F8-O)-Ph          NH        Pe        NH          OH          H         H5236      4-(F8-O)-Ph          NH        C12       NMe         OH          H         H5237      4-(F8-O)-Ph          NH        C12       NEt         OH          H         H5238      4-(F8-O)-Ph          NH        C12       NPr         OH          H         H5239      4-(F8-O)-Ph          NH        (CH2)3 N           OH          H         H5240      4-(F8-O)-Ph          NH        (CH2)4 N           OH          H         H5241      4-(F8-O)-Ph          NH        (CH2)5 N           OH          H         H5242      4-(F8-O)-Ph          NH        C12       O           OH          H         H5243      4-(F8-O)-Ph          NH        Ph        O           OH          H         H5244      4-(F8-O)-Ph          NH        C12       S           OH          H         H5245      4-(F8-O)-Ph          NH        Ph        S           OH          H         H5246      4-(F8-O)-Ph          NMe       H         NH          OH          H         H5247      4-(F8-O)-Ph          NEt       H         NH          OH          H         H5248      4-(F8-O)-Ph          NPr       H         NH          OH          H         H5249      4-(F8-O)-Ph          O         H         NH          OH          H         H5250      4-(F8-O)-Ph          S         H         NH          OH          H         H5251      4-(F9-O)-Ph          NH        H         NH          H           H         H5252      4-(F9-O)-Ph          NH        H         NH          OH          H         H5253      4-(F9-O)-Ph          NH        H         NH          OA6         H         H5254      4-(F9-O)-Ph          NH        H         NH          OA8         H         H5255      4-(F9-O)-Ph          NH        H         NH          OA9         H         H5256      4-(F9-O)-Ph          NH        H         NH          OA10        H         H5257      4-(F9-O)-Ph          NH        H         NH          OA12        H         H5258      4-(F9-O)-Ph          NH        H         NH          OA14        H         H5259      4-(F9-O)-Ph          NH        H         NH          OA16        H         H5260      4- F9-O)-Ph          NH        H         NH          OH          H         A65261      4-(F9-O)-Ph          NH        H         NH          OH          H         A85262      4-(F9-O)-Ph          NH        H         NH          OH          H         A95263      4-(F9-O)-Ph          NH        H         NH          OH          H         A105264      4-(F9-O)-Ph          NH        H         NH          OH          H         A125265      4-(F9-O)-Ph          NH        H         NH          OH          H         A145266      4-(F9-O)-Ph          NH        H         NH          OH          H         A165267      4-(F9-O)-Ph          NH        H         NH          OH          A6        A65268      4-(F9-O)-Ph          NH        H         NH          OH          A8        A85269      4-(F9-O)-Ph          NH        H         NH          OH          A10       A105270      4-(F9-O)-Ph          NH        H         NH          OA2         A2        A25271      4-(F9-O)-Ph          NH        H         NH          OA3         A3        A35272      4-(F9-O)-Ph          NH        H         NH          OA4         A4        A45273      4-(F9-O)-Ph          NH        H         NH          OC6         H         H5274      4-(F9-O)-Ph          NH        H         NH          OC7         H         H5275      4-(F9-O)-Ph          NH        H         NH          OC8         H         H5276      4-(F9-O)-Ph          NH        H         NH          OC10        H         H5277      4-(F9-O)-Ph          NH        H         NH          OC11        H         H5278      4-(F9-O)-Ph          NH        H         NH          OC12        H         H5279      4-(F9-O)-Ph          NH        H         NH          OC14        H         H5280      4-(F9-O)-Ph          NH        H         NH          OC16        H         H5281      4-(F9-O)-Ph          NH        H         NH          C6CO3      H         H5282      4-(F9-O)-Ph          NH        H         NH          C7CO3      H         H5283      4-(F9-O)-Ph          NH        H         NH          C8CO3      H         H5284      4-(F9-O)-Ph          NH        H         NH          C9CO3      H         H5285      4-(F9-O)-Ph          NH        H         NH          C10CO3     H         H5286      4-(F9-O)-Ph          NH        H         NH          C12CO3     H         H5287      4-(F9-O)-Ph          NH        H         NH          C16CO3     H         H5288      4-(F9-O)-Ph          NH        C8        NH          OH          H         H5289      4-(F9-O)-Ph          NH        C9        NH          OH          H         H5290      4-(F9-O)-Ph          NH        C10       NH          OH          H         H5291      4-(F9-O)-Ph          NH        C12       NH          OH          H         H5292      4-(F9-O)-Ph          NH        C16       NH          OH          H         H5293      4-(F9-O)-Ph          NH        F1        NH          OH          H         H5294      4-(F9-O)-Ph          NH        F2        NH          OH          H         H5295      4-(F9-O)-Ph          NH        F3        NH          OH          H         H5296      4-(F9-O)-Ph          NH        F4        NH          OH          H         H5297      4-(F9-O)-Ph          NH        F5        NH          OH          H         H5298      4-(F9-O)-Ph          NH        F6        NH          OH          H         H5299      4-(F9-O)-Ph          NH        F7        NH          OH          H         H5300      4-(F9-O)-Ph          NH        F8        NH          OH          H         H5301      4-(F9-O)-Ph          NH        F9        NH          OH          H         H5302      4-(F9-O)-Ph          NH        F10       NH          OH          H         H5303      4-(F9-O)-Ph          NH        Ph        NH          OH          H         H5304      4-(F9-O)-Ph          NH        Bn        NH          OH          H         H5305      4-(F9-O)-Ph          NH        Pe        NH          OH          H         H5306      4-(F9-O)-Ph          NH        C12       NMe         OH          H         H5307      4-(F9-O)-Ph          NH        C12       NEt         OH          H         H5308      4-(F9-O)-Ph          NH        C12       NPr         OH          H         H5309      4-(F9-O)-Ph          NH        (CH2)3 N           OH          H         H5310      4-(F9-O)-Ph          NH        (CH2)4 N           OH          H         H5311      4-(F9-O)-Ph          NH        (CH2)5 N           OH          H         H5312      4-(F9-O)-Ph          NH        C12       O           OH          H         H5313      4-(F9-O)-Ph          NH        Ph        O           OH          H         H5314      4-(F9-O)-Ph          NH        C12       S           OH          H         H5315      4-(F9-O)-Ph          NH        Ph        S           OH          H         H5316      4-(F9-O)-Ph          NMe       H         NH          OH          H         H5317      4-(F9-O)-Ph          NEt       H         NH          OH          H         H5318      4-(F9-O)-Ph          NPr       H         NH          OH          H         H5319      4-(F9-O)-Ph          O         H         NH          OH          H         H5320      4-(F9-O)-Ph          S         H         NH          OH          H         H5321      4-(F11)-Ph           NH        H         NH          H           H         H5322      4-(F11)-Ph           NH        H         NH          OH          H         H5323      4-(F11)-Ph           NH        H         NH          OA6         H         H5324      4-(F11)-Ph           NH        H         NH          OA8         H         H5325      4-(F11)-Ph           NH        H         NH          OA9         H         H5326      4-(F11)-Ph           NH        H         NH          OA10        H         H5327      4-(F11)-Ph           NH        H         NH          OA12        H         H5328      4-(F11)-Ph           NH        H         NH          OA14        H         H5329      4-(F11)-Ph           NH        H         NH          OA16        H         H5330      4-(F11)-Ph           NH        H         NH          OH          H         A65331      4-(F11)-Ph           NH        H         NH          OH          H         A85332      4-(F11)-Ph           NH        H         NH          OH          H         A95333      4-(F11)-Ph           NH        H         NH          OH          H         A105334      4-(F11)-Ph           NH        H         NH          OH          H         A125335      4-(F11)-Ph           NH        H         NH          OH          H         A145336      4-(F11)-Ph           NH        H         NH          OH          H         A165337      4-(F11)-Ph           NH        H         NH          OH          A6        A65338      4-(F11)-Ph           NH        H         NH          OH          A8        A85339      4-(F11)-Ph           NH        H         NH          OH          A10       A105340      4-(F11)-Ph           NH        H         NH          OA2         A2        A25341      4-(F11)-Ph           NH        H         NH          OA3         A3        A35342      4-(F11)-Ph           NH        H         NH          OA4         A4        A45343      4-(F11)-Ph           NH        H         NH          OC6         H         H5344      4-(F11)-Ph           NH        H         NH          OC7         H         H5345      4-(F11)-Ph           NH        H         NH          OC8         H         H5346      4-(F11)-Ph           NH        H         NH          OC10        H         H5347      4-(F11)-Ph           NH        H         NH          OC11        H         H5348      4-(F11)-Ph           NH        H         NH          OC12        H         H5349      4-(F11)-Ph           NH        H         NH          OC14        H         H5350      4-(F11)-Ph           NH        H         NH          OC16        H         H5351      4-(F11)-Ph           NH        H         NH          C6CO3      H         H5352      4-(F11)-Ph           NH        H         NH          C7CO3      H         H5353      4-(F11)-Ph           NH        H         NH          C8CO3      H         H5354      4-(F11)-Ph           NH        H         NH          C9CO3      H         H5355      4-(F11)-Ph           NH        H         NH          C10CO3     H         H5356      4-(F11)-Ph           NH        H         NH          C12CO3     H         H5357      4-(F11)-Ph           NH        H         NH          C16CO3     H         H5358      4-(F11)-Ph           NH        C8        NH          OH          H         H5359      4-(F11)-Ph           NH        C9        NH          OH          H         H5360      4-(F11)-Ph           NH        C10       NH          OH          H         H5361      4-(F11)-Ph           NH        C12       NH          OH          H         H5362      4-(F11)-Ph           NH        C16       NH          OH          H         H5363      4-(F11)-Ph           NH        F1        NH          OH          H         H5364      4-(F11)-Ph           NH        F2        NH          OH          H         H5365      4-(F11)-Ph           NH        F3        NH          OH          H         H5366      4-(F11)-Ph           NH        F4        NH          OH          H         H5367      4-(F11)-Ph           NH        F5        NH          OH          H         H5368      4-(F11)-Ph           NH        F6        NH          OH          H         H5369      4-(F11)-Ph           NH        F7        NH          OH          H         H5370      4-(F11)-Ph           NH        F8        NH          OH          H         H5371      4-(F11)-Ph           NH        F9        NH          OH          H         H5372      4-(F11)-Ph           NH        F10       NH          OH          H         H5373      4-(F11)-Ph           NH        Ph        NH          OH          H         H5374      4-(F11)-Ph           NH        Bn        NH          OH          H         H5375      4-(F11)-Ph           NH        Pe        NH          OH          H         H5376      4-(F11)-Ph           NH        C12       NMe         OH          H         H5377      4-(F11)-Ph           NH        C12       NEt         OH          H         H5378      4-(F11)-Ph           NH        C12       NPr         OH          H         H5379      4-(F11)-Ph           NH        (CH2)3 N           OH          H         H5380      4-(F11)-Ph           NH        (CH2)4 N           OH          H         H5381      4-(F11)-Ph           NH        (CH2)5 N           OH          H         H5382      4-(F11)-Ph           NH        C12       O           OH          H         H5383      4-(F11)-Ph           NH        Ph        O           OH          H         H5384      4-(F11)-Ph           NH        C12       S           OH          H         H5385      4-(F11)-Ph           NH        Ph        S           OH          H         H5386      4-(F11)-Ph           NMe       H         NH          OH          H         H5387      4-(F11)-Ph           NEt       H         NH          OH          H         H5388      4-(F11)-Ph           NPr       H         NH          OH          H         H5389      4-(F11)-Ph           O         H         NH          OH          H         H5390      4-(F11)-Ph           S         H         NH          OH          H         H5391      4-(F12)-Ph           NH        H         NH          H           H         H5392      4-(F12)-Ph           NH        H         NH          OH          H         H5393      4-(F12)-Ph           NH        H         NH          OA6         H         H5394      4-(F12)-Ph           NH        H         NH          OA8         H         H5395      4-(F12)-Ph           NH        H         NH          OA9         H         H5396      4-(F12)-Ph           NH        H         NH          OA10        H         H5397      4-(F12)-Ph           NH        H         NH          OA12        H         H5398      4-(F12)-Ph           NH        H         NH          OA14        H         H5399      4-(F12)-Ph           NH        H         NH          OA16        H         H5400      4- F12)-Ph           NH        H         NH          OH          H         A65401      4-(F12)-Ph           NH        H         NH          OH          H         A85402      4-(F12)-Ph           NH        H         NH          OH          H         A95403      4-(F12)-Ph           NH        H         NH          OH          H         A105404      4-(F12)-Ph           NH        H         NH          OH          H         A125405      4-(F12)-Ph           NH        H         NH          OH          H         A145406      4-(F12)-Ph           NH        H         NH          OH          H         A165407      4-(F12)-Ph           NH        H         NH          OH          A6        A65408      4-(F12)-Ph           NH        H         NH          OH          A8        A85409      4-(F12)-Ph           NH        H         NH          OH          A10       A105410      4-(F12)-Ph           NH        H         NH          OA2         A2        A25411      4-(F12)-Ph           NH        H         NH          OA3         A3        A35412      4-(F12)-Ph           NH        H         NH          OA4         A4        A45413      4-(F12)-Ph           NH        H         NH          OC6         H         H5414      4-(F12)-Ph           NH        H         NH          OC7         H         H5415      4-(F12)-Ph           NH        H         NH          OC8         H         H5416      4-(F12)-Ph           NH        H         NH          OC10        H         H5417      4-(F12)-Ph           NH        H         NH          OC11        H         H5418      4-(F12)-Ph           NH        H         NH          OC12        H         H5419      4-(F12)-Ph           NH        H         NH          OC14        H         H5420      4-(F12)-Ph           NH        H         NH          OC16        H         H5421      4-(F12)-Ph           NH        H         NH          C6CO3      H         H5422      4-(F12)-Ph           NH        H         NH          C7CO3      H         H5423      4-(F12)-Ph           NH        H         NH          C8CO3      H         H5424      4-(F12)-Ph           NH        H         NH          C9CO3      H         H5425      4-(F12)-Ph           NH        H         NH          C10CO3     H         H5426      4-(F12)-Ph           NH        H         NH          C12CO3     H         H5427      4-(F12)-Ph           NH        H         NH          C16CO3     H         H5428      4-(F12)-Ph           NH        C8        NH          OH          H         H5429      4-(F12)-Ph           NH        C9        NH          OH          H         H5430      4-(F12)-Ph           NH        C10       NH          OH          H         H5431      4-(F12)-Ph           NH        C12       NH          OH          H         H5432      4-(F12)-Ph           NH        C16       NH          OH          H         H5433      4-(F12)-Ph           NH        F1        NH          OH          H         H5434      4-(F12)-Ph           NH        F2        NH          OH          H         H5435      4-(F12)-Ph           NH        F3        NH          OH          H         H5436      4-(F12)-Ph           NH        F4        NH          OH          H         H5437      4-(F12)-Ph           NH        F5        NH          OH          H         H5438      4-(F12)-Ph           NH        F6        NH          OH          H         H5439      4-(F12)-Ph           NH        F7        NH          OH          H         H5440      4-(F12)-Ph           NH        F8        NH          OH          H         H5441      4-(F12)-Ph           NH        F9        NH          OH          H         H5442      4-(F12)-Ph           NH        F10       NH          OH          H         H5443      4-(F12)-Ph           NH        Ph        NH          OH          H         H5444      4-(F12)-Ph           NH        Bn        NH          OH          H         H5445      4-(F12)-Ph           NH        Pe        NH          OH          H         H5446      4-(F12)-Ph           NH        C12       NMe         OH          H         H5447      4-(F12)-Ph           NH        C12       NEt         OH          H         H5448      4-(F12)-Ph           NH        C12       NPr         OH          H         H5449      4-(F12)-Ph           NH        (CH2)3 N           OH          H         H5450      4-(F12)-Ph           NH        (CH2)4 N           OH          H         H5451      4-(F12)-Ph           NH        (CH2)5 N           OH          H         H5452      4-(F12)-Ph           NH        C12       O           OH          H         H5453      4-(F12)-Ph           NH        Ph        O           OH          H         H5454      4-(F12)-Ph           NH        C12       S           OH          H         H5455      4-(F12)-Ph            NH        Ph        S           OH          H         H5456      4-(F12)-Ph            NMe       H         NH          OH          H         H5457      4-(F12)-Ph            NEt       H         NH          OH          H         H5458      4-(F12)-Ph            NPr       H         NH          OH          H         H5459      4-(F12)-Ph            O         H         NH          OH          H         H5460      4-(F12)-Ph            S         H         NH          OH          H         H5461      2-NO2-Ph             NH        H         NH          H           H         H5462      2-NO2-Ph             NH        H         NH          OH          H         H5463      2-NO2-Ph             NH        H         NH          OA6         H         H5464      2-NO2-Ph             NH        H         NH          OA8         H         H5465      2-NO2-Ph             NH        H         NH          OA9         H         H5466      2-NO2-Ph             NH        H         NH          OA10        H         H5467      2-NO2-Ph             NH        H         NH          OA12        H         H5468      2-NO2-Ph             NH        H         NH          OA14        H         H5469      2-NO2-Ph             NH        H         NH          OA16        H         H5470      2-NO2-Ph             NH        H         NH          OH          H         A65471      2-NO2-Ph             NH        H         NH          OH          H         A85472      2-NO2-Ph             NH        H         NH          OH          H         A95473      2-NO2-Ph             NH        H         NH          OH          H         A105474      2-NO2-Ph             NH        H         NH          OH          H         A125475      2-NO2-Ph             NH        H         NH          OH          H         A145476      2-NO2-Ph             NH        H         NH          OH          H         A165477      2-NO2-Ph             NH        H         NH          OH          A6        A65478      2-NO2-Ph             NH        H         NH          OH          A8        A85479      2-NO2-Ph             NH        H         NH          OH          A10       A105480      2-NO2-Ph             NH        H         NH          OA2         A2        A25481      2-NO2-Ph             NH        H         NH          OA3         A3        A35482      2-NO2-Ph             NH        H         NH          OA4         A4        A45483      2-NO2-Ph             NH        H         NH          OC6         H         H5484      2-NO2-Ph             NH        H         NH          OC7         H         H5485      2-NO2-Ph             NH        H         NH          OC8         H         H5486      2-NO2-Ph             NH        H         NH          OC10        H         H5487      2-NO2-Ph             NH        H         NH          OC11        H         H5488      2-NO2-Ph             NH        H         NH          OC12        H         H5489      2-NO2-Ph             NH        H         NH          OC14        H         H5490      2-NO2-Ph             NH        H         NH          OC16        H         H5491      2-NO2-Ph             NH        H         NH          C6CO3      H         H5492      2-NO2-Ph             NH        H         NH          C7CO3      H         H5493      2-NO2-Ph             NH        H         NH          C8CO3      H         H5494      2-NO2-Ph             NH        H         NH          C9CO3      H         H5495      2-NO2-Ph             NH        H         NH          C10CO3     H         H5496      2-NO2-Ph             NH        H         NH          C12CO3     H         H5497      2-NO2-Ph             NH        H         NH          C16CO3     H         H5498      2-NO2-Ph             NH        C8        NH          OH          H         H5499      2-NO2-Ph             NH        C9        NH          OH          H         H5500      2-NO2-Ph             NH        C10       NH          OH          H         H5501      2-NO2-Ph             NH        C12       NH          OH          H         H5502      2-NO2-Ph             NH        C16       NH          OH          H         H5503      2-NO2-Ph             NH        F1        NH          OH          H         H5504      2-NO2-Ph             NH        F2        NH          OH          H         H5505      2-NO2-Ph             NH        F3        NH          OH          H         H5506      2-NO2-Ph             NH        F4        NH          OH          H         H5507      2-NO2-Ph             NH        F5        NH          OH          H         H5508      2-NO2-Ph             NH        F6        NH          OH          H         H5509      2-NO2-Ph             NH        F7        NH          OH          H         H5510      2-NO2-Ph             NH        F8        NH          OH          H         H5511      2-NO2-Ph             NH        F9        NH          OH          H         H5512      2-NO2-Ph             NH        F10       NH          OH          H         H5513      2-NO2-Ph             NH        Ph        NH          OH          H         H5514      2-NO2-Ph             NH        Bn        NH          OH          H         H5515      2-NO2-Ph             NH        Pe        NH          OH          H         H5516      2-NO2-Ph             NH        C12       NMe         OH          H         H5517      2-NO2-Ph             NH        C12       NEt         OH          H         H5518      2-NO2-Ph             NH        C12       NPr         OH          H         H5519      2-NO2-Ph             NH        (CH2)3 N           OH          H         H5520      2-NO2-Ph             NH        (CH2)4 N           OH          H         H5521      2-NO2-Ph             NH        (CH2)5 N           OH          H         H5522      2-NO2-Ph             NH        C12       O           OH          H         H5523      2-NO2-Ph             NH        Ph        O           OH          H         H5524      2-NO2-Ph             NH        C12       S           OH          H         H5525      2-NO2-Ph             NH        Ph        S           OH          H         H5526      2-NO2-Ph             NMe       H         NH          OH          H         H5527      2-NO2-Ph             NEt       H         NH          OH          H         H5528      2-NO2-Ph             NPr       H         NH          OH          H         H5529      2-NO2-Ph             O         H         NH          OH          H         H5530      2-NO2-Ph             S         H         NH          OH          H         H5531      3-NO2-Ph             NH        H         NH          H           H         H5532      3-NO2-Ph             NH        H         NH          OH          H         H5533      3-NO2-Ph             NH        H         NH          OA6         H         H5534      3-NO2-Ph             NH        H         NH          OA8         H         H5535      3-NO2-Ph             NH        H         NH          OA9         H         H5536      3-NO2-Ph             NH        H         NH          OA10        H         H5537      3-NO2-Ph             NH        H         NH          OA12        H         H5538      3-NO2-Ph             NH        H         NH          OA14        H         H5539      3-NO2-Ph             NH        H         NH          OA16        H         H5540      3-NO2-Ph             NH        H         NH          OH          H         A65541      3-NO2-Ph             NH        H         NH          OH          H         A85542      3-NO2-Ph             NH        H         NH          OH          H         A95543      3-NO2-Ph             NH        H         NH          OH          H         A105544      3-NO2-Ph             NH        H         NH          OH          H         A125545      3-NO2-Ph             NH        H         NH          OH          H         A145546      3-NO2-Ph             NH        H         NH          OH          H         A165547      3-NO2-Ph             NH        H         NH          OH          A6        A65548      3-NO2-Ph             NH        H         NH          OH          A8        A85549      3-NO2-Ph             NH        H         NH          OH          A10       A105550      3-NO2-Ph             NH        H         NH          OA2         A2        A25551      3-NO2-Ph             NH        H         NH          OA3         A3        A35552      3-NO2-Ph             NH        H         NH          OA4         A4        A45553      3-NO2-Ph             NH        H         NH          OC6         H         H5554      3-NO2-Ph             NH        H         NH          OC7         H         H5555      3-NO2-Ph             NH        H         NH          OC8         H         H5556      3-NO2-Ph             NH        H         NH          OC10        H         H5557      3-NO2-Ph             NH        H         NH          OC11        H         H5558      3-NO2-Ph             NH        H         NH          OC12        H         H5559      3-NO2-Ph             NH        H         NH          OC14        H         H5560      3-NO2-Ph             NH        H         NH          OC16        H         H5561      3-NO2-Ph             NH        H         NH          C6CO3      H         H5562      3-NO2-Ph             NH        H         NH          C7CO3      H         H5563      3-NO2-Ph             NH        H         NH          C8CO3      H         H5564      3-NO2-Ph             NH        H         NH          C9CO3      H         H5565      3-NO2-Ph             NH        H         NH          C10CO3     H         H5566      3-NO2-Ph             NH        H         NH          C12CO3     H         H5567      3-NO2-Ph             NH        H         NH          C16CO3     H         H5568      3-NO2-Ph             NH        C8        NH          OH          H         H5569      3-NO2-Ph             NH        C9        NH          OH          H         H5570      3-NO2-Ph             NH        C10       NH          OH          H         H5571      3-NO2-Ph             NH        C12       NH          OH          H         H5572      3-NO2-Ph             NH        C16       NH          OH          H         H5573      3-NO2-Ph             NH        F1        NH          OH          H         H5574      3-NO2-Ph             NH        F2        NH          OH          H         H5575      3-NO2-Ph             NH        F3        NH          OH          H         H5576      3-NO2-Ph             NH        F4        NH          OH          H         H5577      3-NO2-Ph             NH        F5        NH          OH          H         H5578      3-NO2-Ph             NH        F6        NH          OH          H         H5579      3-NO2-Ph             NH        F7        NH          OH          H         H5580      3-NO2-Ph             NH        F8        NH          OH          H         H5581      3-NO2-Ph             NH        F9        NH          OH          H         H5582      3-NO2-Ph             NH        F10       NH          OH          H         H5583      3-NO2-Ph             NH        Ph        NH          OH          H         H5584      3-NO2-Ph             NH        Bn        NH          OH          H         H5585      3-NO2-Ph             NH        Pe        NH          OH          H         H5586      3-NO2-Ph             NH        C12       NMe         OH          H         H5587      3-NO2-Ph             NH        C12       NEt         OH          H         H5588      3-NO2-Ph             NH        C12       NPr         OH          H         H5589      3-NO2-Ph             NH        (CH2)3 N           OH          H         H5590      3-NO2-Ph             NH        (CH2)4 N           OH          H         H5591      3-NO2-Ph             NH        (CH2)5 N           OH          H         H5592      3-NO2-Ph             NH        C12       O           OH          H         H5593      3-NO2-Ph             NH        Ph        O           OH          H         H5594      3-NO2-Ph             NH        C12       S           OH          H         H5595      3-NO2-Ph             NH        Ph        S           OH          H         H5596      3-NO2-Ph             NMe       H         NH          OH          H         H5597      3-NO2-Ph             NEt       H         NH          OH          H         H5598      3-NO2-Ph             NPr       H         NH          OH          H         H5599      3-NO2-Ph             O         H         NH          OH          H         H5600      3-NO2-Ph             S         H         NH          OH          H         H5601      4-NO2-Ph             NH        H         NH          H           H         H5602      4-NO2-Ph             NH        H         NH          OH          H         H5603      4-NO2-Ph             NH        H         NH          OA6         H         H5604      4-NO2-Ph             NH        H         NH          OA8         H         H5605      4-NO2-Ph             NH        H         NH          OA9         H         H5606      4-NO2-Ph             NH        H         NH          OA10        H         H5607      4-NO2-Ph             NH        H         NH          OA12        H         H5608      4-NO2-Ph             NH        H         NH          OA14        H         H5609      4-NO2-Ph             NH        H         NH          OA16        H         H5610      4-NO2-Ph             NH        H         NH          OH          H         A65611      4-NO2-Ph             NH        H         NH          OH          H         A85612      4-NO2-Ph             NH        H         NH          OH          H         A95613      4-NO2-Ph             NH        H         NH          OH          H         A105614      4-NO2-Ph             NH        H         NH          OH          H         A125615      4-NO2-Ph             NH        H         NH          OH          H         A145616      4-NO2-Ph             NH        H         NH          OH          H         A165617      4-NO2-Ph             NH        H         NH          OH          A6        A65618      4-NO2-Ph             NH        H         NH          OH          A8        A85619      4-NO2-Ph             NH        H         NH          OH          A10       A105620      4-NO2-Ph             NH        H         NH          OA2         A2        A25621      4-NO2-Ph             NH        H         NH          OA3         A3        A35622      4-NO2-Ph             NH        H         NH          OA4         A4        A45623      4-NO2-Ph             NH        H         NH          OC6         H         H5624      4-NO2-Ph             NH        H         NH          OC7         H         H5625      4-NO2-Ph             NH        H         NH          OC8         H         H5626      4-NO2-Ph             NH        H         NH          OC10        H         H5627      4-NO2-Ph             NH        H         NH          OC11        H         H5628      4-NO2-Ph             NH        H         NH          OC12        H         H5629      4-NO2-Ph             NH        H         NH          OC14        H        H5630      4-NO2-Ph             NH        H         NH          OC16        H        H5631      4-NO2-Ph             NH        H         NH          C6CO3      H        H5632      4-NO2-Ph             NH        H         NH          C7CO3      H        H5633      4-NO2-Ph             NH        H         NH          C8CO3      H        H5634      4-NO2-Ph             NH        H         NH          C9CO3      H        H5635      4-NO2-Ph             NH        H         NH          C10CO3     H        H5636      4-NO2-Ph             NH        H         NH          C12CO3     H        H5637      4-NO2-Ph             NH        H         NH          C16CO3     H        H5638      4-NO2-Ph             NH        C8        NH          OH          H        H5639      4-NO2-Ph             NH        C9        NH          OH          H        H5640      4-NO2-Ph             NH        C10       NH          OH          H        H5641      4-NO2-Ph             NH        C12       NH          OH          H        H5642      4-NO2-Ph             NH        C16       NH          OH          H        H5643      4-NO2-Ph             NH        F1        NH          OH          H        H5644      4-NO2-Ph             NH        F2        NH          OH          H        H5645      4-NO2-Ph             NH        F3        NH          OH          H        H5646      4-NO2-Ph             NH        F4        NH          OH          H        H5647      4-NO2-Ph             NH        F5        NH          OH          H        H5648      4-NO2-Ph             NH        F6        NH          OH          H        H5649      4-NO2-Ph             NH        F7        NH          OH          H        H5650      4-NO2-Ph             NH        F8        NH          OH          H        H5651      4-NO2-Ph             NH        F9        NH          OH          H        H5652      4-NO2-Ph             NH        F10       NH          OH          H        H5653      4-NO2-Ph             NH        Ph        NH          OH          H        H5654      4-NO2-Ph             NH        Bn        NH          OH          H        H5655      4-NO2-Ph             NH        Pe        NH          OH          H        H5656      4-NO2-Ph             NH        C12       We          OH          H        H5657      4-NO2-Ph             NH        C12       NEt         OH          H        H5658      4-NO2-Ph            NH        C12       NPr         OH          H         H5659      4-NO2-Ph            NH        (CH2)3 N           OH          H         H5660      4-NO2-Ph            NH        (CH2)4 N           OH          H         H5661      4-NO2-Ph            NH        (CH2)5 N           OH          H         H5662      4-NO2-Ph            NH        C12       O           OH          H         H5663      4-NO2-Ph            NH        Ph        O           OH          H         H5664      4-NO2-Ph            NH        C12       S           OH          H         H5665      4-NO2-Ph            NH        Ph        S           OH          H         H5666      4-NO2-Ph            NMe       H         NH          OH          H         H5667      4-NO2-Ph            NEt       H         NH          OH          H         H5668      4-NO2-Ph            NPr       H         NH          OH          H         H5669      4-NO2-Ph            O         H         NH          OH          H         H5670      4-NO2-Ph            S         H         NH          OH          H         H5671      2-OH-Ph              NH        H         NH          H           H         H5672      2-OH-Ph              NH        H         NH          OH          H         H5673      2-OH-Ph              NH        H         NH          OA6         H         H5674      2-OH-Ph              NH        H         NH          OA8         H         H5675      2-OH-Ph              NH        H         NH          OA9         H         H5676      2-OH-Ph              NH        H         NH          OA10        H         H5677      2-OH-Ph              NH        H         NH          OA12        H         H5678      2-OH-Ph              NH        H         NH          OA14        H         H5679      2-OH-Ph              NH        H         NH          OA16        H         H5680      2-OH-Ph              NH        H         NH          OH          H         A65681      2-OH-Ph              NH        H         NH          OH          H         A85682      2-OH-Ph              NH        H         NH          OH          H         A95683      2-OH-Ph              NH        H         NH          OH          H         A105684      2-OH-Ph              NH        H         NH          OH          H         A125685      2-OH-Ph              NH        H         NH          OH          H         A145686      2-OH-Ph              NH        H         NH          OH          H         A165687      2-OH-Ph              NH        H         NH          OH          A6        A65688      2-OH-Ph              NH        H         NH          OH          A8        A85689      2-OH-Ph              NH        H         NH          OH          A10       A105690      2-OH-Ph              NH        H         NH          OA2         A2        A25691      2-OH-Ph              NH        H         NH          OA3         A3        A35692      2-OH-Ph              NH        H         NH          OA4         A4        A45693      2-OH-Ph              NH        H         NH          OC6         H         H5694      2-OH-Ph              NH        H         NH          OC7         H         H5695      2-OH-Ph              NH        H         NH          OC8         H         H5696      2-OH-Ph              NH        H         NH          OC10        H         H5697      2-OH-Ph              NH        H         NH          OC11        H         H5698      2-OH-Ph              NH        H         NH          OC12        H         H5699      2-OH-Ph              NH        H         NH          OC14        H         H5700      2-OH-Ph              NH        H         NH          OC16        H         H5701      2-OH-Ph              NH        H         NH          C6CO3      H         H5702      2-OH-Ph              NH        H         NH          C7CO3      H         H5703      2-OH-Ph              NH        H         NH          C8CO3      H         H5704      2-OH-Ph              NH        H         NH          C9CO3      H         H5705      2-OH-Ph              NH        H         NH          C10CO3     H         H5706      2-OH-Ph              NH        H         NH          C12CO3     H         H5707      2-OH-Ph              NH        H         NH          C16CO3     H         H5708      2-OH-Ph              NH        C8        NH          OH          H         H5709      2-OH-Ph              NH        C9        NH          OH          H         H5710      2-OH-Ph              NH        C10       NH          OH          H         H5711      2-OH-Ph              NH        C12       NH          OH          H         H5712      2-OH-Ph              NH        C16       NH          OH          H         H5713      2-OH-Ph              NH        F1        NH          OH          H         H5714      2-OH-Ph              NH        F2        NH          OH          H         H5715      2-OH-Ph              NH        F3        NH          OH          H         H5716      2-OH-Ph              NH        F4        NH          OH          H         H5717      2-OH-Ph              NH        F5        NH          OH          H         H5718      2-OH-Ph              NH        F6        NH          OH          H         H5719      2-OH-Ph              NH        F7        NH          OH          H         H5720      2-OH-Ph              NH        F8        NH          OH          H         H5721      2-OH-Ph              NH        F9        NH          OH          H         H5722      2-OH-Ph              NH        F10       NH          OH          H         H5723      2-OH-Ph              NH        Ph        NH          OH          H         H5724      2-OH-Ph              NH        Bn        NH          OH          H         H5725      2-OH-Ph              NH        Pe        NH          OH          H         H5726      2-OH-Ph              NH        C12       NMe         OH          H         H5727      2-OH-Ph              NH        C12       NEt         OH          H         H5728      2-OH-Ph              NH        C12       NPr         OH          H         H5729      2-OH-Ph              NH        (CH2)3 N           OH          H         H5730      2-OH-Ph              NH        (CH2)4 N           OH          H         H5731      2-OH-Ph              NH        (CH2)5 N           OH          H         H5732      2-OH-Ph              NH        C12       O           OH          H         H5733      2-OH-Ph              NH        Ph        O           OH          H         H5734      2-OH-Ph              NH        C12       S           OH          H         H5735      2-OH-Ph              NH        Ph        S           OH          H         H5736      2-OH-Ph              NMe       H         NH          OH          H         H5737      2-OH-Ph              NEt       H         NH          OH          H         H5738      2-OH-Ph              NPr       H         NH          OH          H         H5739      2-OH-Ph              O         H         NH          OH          H         H5740      2-OH-Ph              S         H         NH          OH          H         H5741      3-OH-Ph              NH        H         NH          H           H         H5742      3-OH-Ph              NH        H         NH          OH          H         H5743      3-OH-Ph              NH        H         NH          OA6         H         H5744      3-OH-Ph              NH        H         NH          OA8         H         H5745      3-OH-Ph              NH        H         NH          OA9         H         H5746      3-OH-Ph              NH        H         NH          OA10        H         H5747      3-OH-Ph              NH        H         NH          OA12        H         H5748      3-OH-Ph              NH        H         NH          OA14        H         H5749      3-OH-Ph              NH        H         NH          OA16        H         H5750      3-OH-Ph              NH        H         NH          OH          H         A65751      3-OH-Ph              NH        H         NH          OH          H         A85752      3-OH-Ph              NH        H         NH          OH          H         A95753      3-OH-Ph              NH        H         NH          OH          H         A105754      3-OH-Ph              NH        H         NH          OH          H         A125755      3-OH-Ph              NH        H         NH          OH          H         A145756      3-OH-Ph              NH        H         NH          OH          H         A165757      3-OH-Ph              NH        H         NH          OH          A6        A65758      3-OH-Ph              NH        H         NH          OH          A8        A85759      3-OH-Ph              NH        H         NH          OH          A10       A105760      3-OH-Ph              NH        H         NH          OA2         A2        A25761      3-OH-Ph              NH        H         NH          OA3         A3        A35762      3-OH-Ph              NH        H         NH          OA4         A4        A45763      3-OH-Ph              NH        H         NH          OC6         H         H5764      3-OH-Ph              NH        H         NH          OC7         H         H5765      3-OH-Ph              NH        H         NH          OC8         H         H5766      3-OH-Ph              NH        H         NH          OC10        H         H5767      3-OH-Ph              NH        H         NH          OC11        H         H5768      3-OH-Ph              NH        H         NH          OC12        H         H5769      3-OH-Ph              NH        H         NH          OC14        H         H5770      3-OH-Ph              NH        H         NH          OC16        H         H5771      3-OH-Ph              NH        H         NH          C6CO3      H         H5772      3-OH-Ph              NH        H         NH          C7CO3      H         H5773      3-OH-Ph              NH        H         NH          C8CO3      H         H5774      3-OH-Ph              NH        H         NH          C9CO3      H         H5775      3-OH-Ph              NH        H         NH          C10CO3     H         H5776      3-OH-Ph              NH        H         NH          C12CO3     H         H5777      3-OH-Ph              NH        H         NH          C16CO3     H         H5778      3-OH-Ph              NH        C8        NH          OH          H         H5779      3-OH-Ph              NH        C9        NH          OH          H         H5780      3-OH-Ph              NH        C10       NH          OH          H         H5781      3-OH-Ph              NH        C12       NH          OH          H         H5782      3-OH-Ph              NH        C16       NH          OH          H         H5783      3-OH-Ph              NH        F1        NH          OH          H         H5784      3-OH-Ph              NH        F2        NH          OH          H         H5785      3-OH-Ph              NH        F3        NH          OH          H         H5786      3-OH-Ph              NH        F4        NH          OH          H         H5787      3-OH-Ph              NH        F5        NH          OH          H         H5788      3-OH-Ph              NH        F6        NH          OH          H         H5789      3-OH-Ph              NH        F7        NH          OH          H         H5790      3-OH-Ph              NH        F8        NH          OH          H         H5791      3-OH-Ph              NH        F9        NH          OH          H         H5792      3-OH-Ph              NH        F10       NH          OH          H         H5793      3-OH-Ph              NH        Ph        NH          OH          H         H5794      3-OH-Ph              NH        Bn        NH          OH          H         H5795      3-OH-Ph              NH        Pe        NH          OH          H         H5796      3-OH-Ph              NH        C12       NMe         OH          H         H5797      3-OH-Ph              NH        C12       NEt         OH          H         H5798      3-OH-Ph              NH        C12       NPr         OH          H         H5799      3-OH-Ph              NH        (CH2)3 N           OH          H         H5800      3-OH-Ph              NH        (CH2)4 N           OH          H         H5801      3-OH-Ph              NH        (CH2)5 N           OH          H         H5802      3-OH-Ph              NH        C12       O           OH          H         H5803      3-OH-Ph              NH        Ph        O           OH          H         H5804      3-OH-Ph              NH        C12       S           OH          H         H5805      3-OH-Ph              NH        Ph        S           OH          H         H5806      3-OH-Ph              NMe       H         NH          OH          H         H5807      3-OH-Ph              NEt       H         NH          OH          H         H5808      3-OH-Ph              NPr       H         NH          OH          H         H5809      3-OH-Ph              O         H         NH          OH          H         H5810      3-OH-Ph              S         H         NH          OH          H         H5811      4-OH-Ph              NH        H         NH          H           H         H5812      4-OH-Ph              NH        H         NH          OH          H         H5813      4-OH-Ph              NH        H         NH          OA6         H         H5814      4-OH-Ph              NH        H         NH          OA8         H         H5815      4-OH-Ph              NH        H         NH          OA9         H         H5816      4-OH-Ph              NH        H         NH          OA10        H         H5817      4-OH-Ph              NH        H         NH          OA12        H         H5818      4-OH-Ph              NH        H         NH          OA14        H         H5819      4-OH-Ph              NH        H         NH          OA16        H         H5820      4-OH-Ph              NH        H         NH          OH          H         A65821      4-OH-Ph              NH        H         NH          OH          H         A85822      4-OH-Ph              NH        H         NH          OH          H         A95823      4-OH-Ph              NH        H         NH          OH          H         A105824      4-OH-Ph              NH        H         NH          OH          H         A125825      4-OH-Ph              NH        H         NH          OH          H         A145826      4-OH-Ph              NH        H         NH          OH          H         A165827      4-OH-Ph              NH        H         NH          OH          A6        A65828      4-OH-Ph              NH        H         NH          OH          A8        A85829      4-OH-Ph              NH        H         NH          OH          A10       A105830      4-OH-Ph              NH        H         NH          OA2         A2        A25831      4-OH-Ph              NH        H         NH          OA3         A3        A35832      4-OH-Ph              NH        H         NH          OA4         A4        A45833      4-OH-Ph              NH        H         NH          OC6         H         H5834      4-OH-Ph              NH        H         NH          OC7         H         H5835      4-OH-Ph              NH        H         NH          OC8         H         H5836      4-OH-Ph              NH        H         NH          OC10        H         H5837      4-OH-Ph              NH        H         NH          OC11        H         H5838      4-OH-Ph              NH        H         NH          OC12        H         H5839      4-OH-Ph              NH        H         NH          OC14        H         H5840      4-OH-Ph              NH        H         NH          OC16        H         H5841      4-OH-Ph              NH        H         NH          C6CO3      H         H5842      4-OH-Ph              NH        H         NH          C7CO3      H         H5843      4-OH-Ph              NH        H         NH          C8CO3      H         H5844      4-OH-Ph              NH        H         NH          C9CO3      H         H5845      4-OH-Ph              NH        H         NH          C10CO3     H         H5846      4-OH-Ph              NH        H         NH          C12CO3     H         H5847      4-OH-Ph              NH        H         NH          C16CO3     H         H5848      4-OH-Ph              NH        C8        NH          OH          H         H5849      4-OH-Ph              NH        C9        NH          OH          H         H5850      4-OH-Ph              NH        C10       NH          OH          H         H5851      4-OH-Ph              NH        C12       NH          OH          H         H5852      4-OH-Ph              NH        C16       NH          OH          H         H5853      4-OH-Ph              NH        F1        NH          OH          H         H5854      4-OH-Ph              NH        F2        NH          OH          H         H5855      4-OH-Ph              NH        F3        NH          OH          H         H5856      4-OH-Ph              NH        F4        NH          OH          H         H5857      4-OH-Ph              NH        F5        NH          OH          H         H5858      4-OH-Ph              NH        F6        NH          OH          H         H5859      4-OH-Ph              NH        F7        NH          OH          H         H5860      4-OH-Ph              NH        F8        NH          OH          H         H5861      4-OH-Ph              NH        F9        NH          OH          H         H5862      4-OH-Ph              NH        F10       NH          OH          H         H5863      4-OH-Ph              NH        Ph        NH          OH          H         H5864      4-OH-Ph              NH        Bn        NH          OH          H         H5865      4-OH-Ph              NH        Pe        NH          OH          H         H5866      4-OH-Ph              NH        C12       NMe         OH          H         H5867      4-OH-Ph              NH        C12       NEt         OH          H         H5868      4-OH-Ph              NH        C12       NPr         OH          H         H5869      4-OH-Ph              NH        (CH2)3 N           OH          H         H5870      4-OH-Ph              NH        (CH2)4 N           OH          H         H5871      4-OH-Ph              NH        (CH2)5 N           OH          H         H5872      4-OH-Ph              NH        C12       O           OH          H         H5873      4-OH-Ph              NH        Ph        O           OH          H         H5874      4-OH-Ph              NH        C12       S           OH          H         H5875      4-OH-Ph              NH        Ph        S           OH          H         H5876      4-OH-Ph              NMe       H         NH          OH          H         H5877      4-OH-Ph              NEt       H         NH          OH          H         H5878      4-OH-Ph              NPr       H         NH          OH          H         H5879      4-OH-Ph              O         H         NH          OH          H         H5880      4-OH-Ph              S         H         NH          OH          H         H5881      4-Mor-Ph             NH        H         NH          H           H         H5882      4-Mor-Ph             NH        H         NH          OH          H         H5883      4-Mor-Ph             NH        H         NH          OA6         H         H5884      4-Mor-Ph             NH        H         NH          OA8         H         H5885      4-Mor-Ph             NH        H         NH          OA9         H         H5886      4-Mor-Ph             NH        H         NH          OA10        H         H5887      4-Mor-Ph             NH        H         NH          OA12        H         H5888      4-Mor-Ph             NH        H         NH          OA14        H         H5889      4-Mor-Ph             NH        H         NH          OA16        H         H5890      4-Mor-Ph             NH        H         NH          OH          H         A65891      4-Mor-Ph             NH        H         NH          OH          H         A85892      4-Mor-Ph             NH        H         NH          OH          H         A95893      4-Mor-Ph             NH        H         NH          OH          H         A105894      4-Mor-Ph             NH        H         NH          OH          H         A125895      4-Mor-Ph             NH        H         NH          OH          H         A145896      4-Mor-Ph             NH        H         NH          OH          H         A165897      4-Mor-Ph             NH        H         NH          OH          A6        A65898      4-Mor-Ph             NH        H         NH          OH          A8        A85899      4-Mor-Ph             NH        H         NH          OH          A10       A105900      4-Mor-Ph             NH        H         NH          OA2         A2        A25901      4-Mor-Ph             NH        H         NH          OA3         A3        A35902      4-Mor-Ph             NH        H         NH          OA4         A4        A45903      4-Mor-Ph             NH        H         NH          OC6         H         H5904      4-Mor-Ph             NH        H         NH          OC7         H         H5905      4-Mor-Ph             NH        H         NH          OC8         H         H5906      4-Mor-Ph             NH        H         NH          OC10        H         H5907      4-Mor-Ph             NH        H         NH          OC11        H         H5908      4-Mor-Ph             NH        H         NH          OC12        H         H5909      4-Mor-Ph             NH        H         NH          OC14        H         H5910      4-Mor-Ph             NH        H         NH          OC16        H         H5911      4-Mor-Ph             NH        H         NH          C6CO3      H         H5912      4-Mor-Ph             NH        H         NH          C7CO3      H         H5913      4-Mor-Ph             NH        H         NH          C8CO3      H         H5914      4-Mor-Ph             NH        H         NH          C9CO3      H         H5915      4-Mor-Ph             NH        H         NH          C10CO3     H         H5916      4-Mor-Ph             NH        H         NH          C12CO3     H         H5917      4-Mor-Ph             NH        H         NH          C16CO3     H         H5918      4-Mor-Ph             NH        C8        NH          OH          H         H5919      4-Mor-Ph             NH        C9        NH          OH          H         H5920      4-Mor-Ph             NH        C10       NH          OH          H         H5921      4-Mor-Ph             NH        C12       NH          OH          H         H5922      4-Mor-Ph             NH        C16       NH          OH          H         H5923      4-Mor-Ph             NH        F1        NH          OH          H         H5924      4-Mor-Ph             NH        F2        NH          OH          H         H5925      4-Mor-Ph             NH        F3        NH          OH          H         H5926      4-Mor-Ph             NH        F4        NH          OH          H         H5927      4-Mor-Ph             NH        F5        NH          OH          H         H5928      4-Mor-Ph             NH        F6        NH          OH          H         H5929      4-Mor-Ph             NH        F7        NH          OH          H         H5930      4-Mor-Ph             NH        F8        NH          OH          H         H5931      4-Mor-Ph             NH        F9        NH          OH          H         H5932      4-Mor-Ph             NH        F10       NH          OH          H         H5933      4-Mor-Ph             NH        Ph        NH          OH          H         H5934      4-Mor-Ph             NH        Bn        NH          OH          H         H5935      4-Mor-Ph             NH        Pe        NH          OH          H         H5936      4-Mor-Ph             NH        C12       NMe         OH          H         H5937      4-Mor-Ph             NH        C12       NEt         OH          H         H5938      4-Mor-Ph             NH        C12       NPr         OH          H         H5939      4-Mor-Ph             NH        (CH2)3 N           OH          H         H5940      4-Mor-Ph             NH        (CH2)4 N           OH          H         H5941      4-Mor-Ph             NH        (CH2)5 N           OH          H         H5942      4-Mor-Ph             NH        C12       O           OH          H         H5943      4-Mor-Ph             NH        Ph        O           OH          H         H5944      4-Mor-Ph             NH        C12       S           OH          H         H5945      4-Mor-Ph             NH        Ph        S           OH          H         H5946      4-Mor-Ph             NMe       H         NH          OH          H         H5947      4-Mor-Ph             NEt       H         NH          OH          H         H5948      4-Mor-Ph             NPr       H         NH          OH          H         H5949      4-Mor-Ph             O         H         NH          OH          H         H5950      4-Mor-Ph             S         H         NH          OH          H         H5951      4-PA-Ph              NH        H         NH          H           H         H5952      4-PA-Ph              NH        H         NH          OH          H         H5953      4-PA-Ph              NH        H         NH          OA6         H         H5954      4-PA-Ph              NH        H         NH          OA8         H         H5955      4-PA-Ph              NH        H         NH          OA9         H         H5956      4-PA-Ph              NH        H         NH          OA10        H         H5957      4-PA-Ph              NH        H         NH          OA12        H         H5958      4-PA-Ph              NH        H         NH          OA14        H         H5959      4-PA-Ph              NH        H         NH          OA16        H         H5960      4-PA-Ph              NH        H         NH          OH          H         A65961      4-PA-Ph              NH        H         NH          OH          H         A85962      4-PA-Ph              NH        H         NH          OH          H         A95963      4-PA-Ph              NH        H         NH          OH          H         A105964      4-PA-Ph              NH        H         NH          OH          H         A125965      4-PA-Ph              NH        H         NH          OH          H         A145966      4-PA-Ph              NH        H         NH          OH          H         A165967      4-PA-Ph              NH        H         NH          OH          A6        A65968      4-PA-Ph              NH        H         NH          OH          A8        A85969      4-PA-Ph              NH        H         NH          OH          A10       A105970      4-PA-Ph              NH        H         NH          OA2         A2        A25971      4-PA-Ph              NH        H         NH          OA3         A3        A35972      4-PA-Ph              NH        H         NH          OA4         A4        A45973      4-PA-Ph              NH        H         NH          OC6         H         H5974      4-PA-Ph              NH        H         NH          OC7         H         H5975      4-PA-Ph              NH        H         NH          OC8         H         H5976      4-PA-Ph              NH        H         NH          OC10        H         H5977      4-PA-Ph              NH        H         NH          OC11        H         H5978      4-PA-Ph              NH        H         NH          OC12        H         H5979      4-PA-Ph              NH        H         NH          OC14        H         H5980      4-PA-Ph              NH        H         NH          OC16        H         H5981      4-PA-Ph              NH        H         NH          C6CO3      H         H5982      4-PA-Ph              NH        H         NH          C7CO3      H         H5983      4-PA-Ph              NH        H         NH          C8CO3      H         H5984      4-PA-Ph              NH        H         NH          C9CO3      H         H5985      4-PA-Ph              NH        H         NH          C10CO3     H         H5986      4-PA-Ph              NH        H         NH          C12CO3     H         H5987      4-PA-Ph              NH        H         NH          C16CO3     H         H5988      4-PA-Ph              NH        C8        NH          OH          H         H5989      4-PA-Ph              NH        C9        NH          OH          H         H5990      4-PA-Ph              NH        C10       NH          OH          H         H5991      4-PA-Ph              NH        C12       NH          OH          H         H5992      4-PA-Ph              NH        C16       NH          OH          H         H5993      4-PA-Ph              NH        F1        NH          OH          H         H5994      4-PA-Ph              NH        F2        NH          OH          H         H5995      4-PA-Ph              NH        F3        NH          OH          H         H5996      4-PA-Ph              NH        F4        NH          OH          H         H5997      4-PA-Ph              NH        F5        NH          OH          H         H5998      4-PA-Ph              NH        F6        NH          OH          H         H5999      4-PA-Ph              NH        F7        NH          OH          H         H6000      4-PA-Ph              NH        F8        NH          OH          H         H6001      4-PA-Ph              NH        F9        NH          OH          H         H6002      4-PA-Ph              NH        F10       NH          OH          H         H6003      4-PA-Ph              NH        Ph        NH          OH          H         H6004      4-PA-Ph              NH        Bn        NH          OH          H         H6005      4-PA-Ph              NH        Pe        NH          OH          H         H6006      4-PA-Ph              NH        C12       HMe         OH          H         H6007      4-PA-Ph              NH        C12       NEt         OH          H         H6008      4-PA-Ph              NH        C12       NPr         OH          H         H6009      4-PA-Ph              NH        (CH2)3 N           OH          H         H6010      4-PA-Ph              NH        (CH2)4 N           OH          H         H6011      4-PA-Ph              NH        (CH2)5 N           OH          H         H6012      4-PA-Ph              NH        C12       O           OH          H         H6013      4-PA-Ph              NH        Ph        O           OH          H         H6014      4-PA-Ph              NH        C12       S           OH          H         H6015      4-PA-Ph              NH        Ph        S           OH          H         H6016      4-PA-Ph              NMe       H         NH          OH          H         H6017      4-PA-Ph              NEt       H         NH          OH          H         H6018      4-PA-Ph              NPr       H         NH          OH          H         H6019      4-PA-Ph              O         H         NH          OH          H         H6020      4-PA-Ph              S         H         NH          OH          H         H6021      3-CN-Ph              NH        H         NH          H           H         H6022      3-CN-Ph              NH        H         NH          OH          H         H6023      3-CN-Ph              NH        H         NH          OA6         H         H6024      3-CN-Ph              NH        H         NH          OA8         H         H6025      3-CN-Ph              NH        H         NH          OA9         H         H6026      3-CN-Ph              NH        H         NH          OA10        H         H6027      3-CN-Ph              NH        H         NH          OA12        H         H6028      3-CN-Ph              NH        H         NH          OA14        H         H6029      3-CN-Ph              NH        H         NH          OA16        H         H6030      3-CN-Ph              NH        H         NH          OH          H         A66031      3-CN-Ph              NH        H         NH          OH          H         A86032      3-CN-Ph              NH        H         NH          OH          H         A96033      3-CN-Ph              NH        H         NH          OH          H         A106034      3-CN-Ph              NH        H         NH          OH          H         A126035      3-CN-Ph              NH        H         NH          OH          H         A146036      3-CN-Ph              NH        H         NH          OH          H         A166037      3-CN-Ph              NH        H         NH          OH          A6        A66038      3-CN-Ph              NH        H         NH          OH          A8        A86039      3-CN-Ph              NH        H         NH          OH          A10       A106040      3-CN-Ph              NH        H         NH          OA2         A2        A26041      3-CN-Ph              NH        H         NH          OA3         A3        A36042      3-CN-Ph              NH        H         NH          OA4         A4        A46043      3-CN-Ph              NH        H         NH          OC6         H         H6044      3-CN-Ph              NH        H         NH          OC7         H         H6045      3-CN-Ph              NH        H         NH          OC8         H         H6046      3-CN-Ph              NH        H         NH          OC10        H         H6047      3-CN-Ph              NH        H         NH          OC11        H         H6048      3-CN-Ph              NH        H         NH          OC12        H         H6049      3-CN-Ph              NH        H         NH          OC14        H         H6050      3-CN-Ph              NH        H         NH          OC16        H         H6051      3-CN-Ph              NH        H         NH          C6CO3      H         H6052      3-CN-Ph              NH        H         NH          C7CO3      H         H6053      3-CN-Ph              NH        H         NH          C8CO3      H         H6054      3-CN-Ph              NH        H         NH          C9CO3      H         H6055      3-CN-Ph              NH        H         NH          C10CO3     H         H6056      3-CN-Ph              NH        H         NH          C12CO3     H         H6057      3-CN-Ph              NH        H         NH          C16CO3     H         H6058      3-CN-Ph              NH        C8        NH          OH          H         H6059      3-CN-Ph              NH        C9        NH          OH          H         H6060      3-CN-Ph              NH        C10       NH          OH          H         H6061      3-CN-Ph              NH        C12       NH          OH          H         H6062      3-CN-Ph              NH        C16       NH          OH          H         H6063      3-CN-Ph              NH        F1        NH          OH          H         H6064      3-CN-Ph              NH        F2        NH          OH          H         H6065      3-CN-Ph              NH        F3        NH          OH          H         H6066      3-CN-Ph              NH        F4        NH          OH          H         H6067      3-CN-Ph              NH        F5        NH          OH          H         H6068      3-CN-Ph              NH        F6        NH          OH          H         H6069      3-CN-Ph              NH        F7        NH          OH          H         H6070      3-CN-Ph              NH        F8        NH          OH          H         H6071      3-CN-Ph              NH        F9        NH          OH          H         H6072      3-CN-Ph              NH        F10       NH          OH          H         H6073      3-CN-Ph              NH        Ph        NH          OH          H         H6074      3-CN-Ph              NH        Bn        NH          OH          H         H6075      3-CN-Ph              NH        Pe        NH          OH          H         H6076      3-CN-Ph              NH        C12       NMe         OH          H         H6077      3-CN-Ph              NH        C12       NEt         OH          H         H6078      3-CN-Ph              NH        C12       NPr         OH          H         H6079      3-CN-Ph              NH        (CH2)3 N           OH          H         H6080      3-CN-Ph              NH        (CH2)4 N           OH          H         H6081      3-CN-Ph              NH        (CH2)5 N           OH          H         H6082      3-CN-Ph              NH        C12       O           OH          H         H6083      3-CN-Ph              NH        Ph        O           OH          H         H6084      3-CN-Ph              NH        C12       S           OH          H         H6085      3-CN-Ph              NH        Ph        S           OH          H         H6086      3-CN-Ph              NMe       H         NH          OH          H         H6087      3-CN-Ph              NEt       H         NH          OH          H         H6088      3-CN-Ph              NPr       H         NH          OH          H         H6089      3-CN-Ph              O         H         NH          OH          H         H6090      3-CN-Ph              S         H         NH          OH          H         H6091      F1                   NH        H         NH          H           H         H6092      F1                   NH        H         NH          OH          H         H6093      F1         NH         H          NH         OA6         H        H6094      F1         NH         H          NH         OA8         H        H6095      F1         NH         H          NH         OA9         H        H6096      F1         NH         H          NH         OA10        H        H6097      F1         NH         H          NH         OA12        H        H6098      F1         NH         H          NH         OA14        H        H6099      F1         NH         H          NH         OA16        H        H6100      F1         NH         H          NH         OH          H        A66101      F1         NH         H          NH         OH          H        A86102      F1         NH         H          NH         OH          H        A96103      F1         NH         H          NH         OH          H        A106104      F1         NH         H          NH         OH          H        A126105      F1         NH         H          NH         OH          H        A146106      F1         NH         H          NH         OH          H        A166107      F1         NH         H          NH         OH          A6       A66108      F1         NH         H          NH         OH          A8       A86109      F1         NH         H          NH         OH          A10      A106110      F1         NH         H          NH         OA2         A2       A26111      F1         NH         H          NH         OA3         A3       A36112      F1         NH         H          NH         OA4         A4       A46113      F1         NH         H          NH         OC6         H        H6114      F1         NH         H          NH         OC7         H        H6115      F1         NH         H          NH         OC8         H        H6116      F1         NH         H          NH         OC10        H        H6117      F1         NH         H          NH         OC11        H        H6118      F1         NH         H          NH         OC12        H        H6119      F1         NH         H          NH         OC14        H        H6120      F1         NH         H          NH         OC16        H        H6121      F1         NH         H          NH         C6CO3      H        H6122      F1         NH         H          NH         C7CO3      H        H6123      F1         NH         H          NH         C8CO3      H        H6124      F1         NH         H          NH         C9CO3      H        H6125      F1         NH         H          NH         C10CO3     H        H6126      F1         NH         H          NH         C12CO3     H        H6127      F1         NH         H          NH         C16CO3     H        H6128      F1         NH         C8         NH         OH          H        H6129      F1         NH         C9         NH         OH          H        H6130      F1         NH         C10        NH         OH          H        H6131      F1         NH         C12        NH         OH          H        H6132      F1         NH         C16        NH         OH          H        H6133      F1         NH         F1         NH         OH          H        H6134      F1         NH         F2         NH         OH          H        H6135      F1         NH         F3         NH         OH          H        H6136      F1         NH         F4         NH         OH          H        H6137      F1         NH         F5         NH         OH          H        H6138      F1         NH         F6         NH         OH          H        H6139      F1         NH         F7         NH         OH          H        H6140      F1         NH         F8         NH         OH          H        H6141      F1         NH         F9         NH         OH          H        H6142      F1         NH         F10        NH         OH          H        H6143      F1         NH         Ph         NH         OH          H        H6144      F1         NH         Bn         NH         OH          H        H6145      F1         NH         Pe         NH         OH          H        H6146      F1         NH         C12        NMe        OH          H        H6147      F1         NH         C12        NEt        OH          H        H6148      F1         NH         C12        NPr        OH          H        H6149      F1         NH         (CH2)3  N          OH          H        H6150      F1         NH         (CH2)4  N          OH          H        H6151      F1         NH         (CH2)5  N          OH          H        H6152      F1         NH         C12        O          OH          H        H6153      F1         NH         Ph         O          OH          H        H6154      F1         NH         C12        S          OH          H        H6155      F1         NH         Ph         S          OH          H        H6156      F1         NMe        H          NH         OH          H        H6157      F1         NEt        H          NH         OH          H        H6158      F1         NPr        H          NH         OH          H        H6159      F1         O          H          NH         OH          H        H6160      F1         S          H          NH         OH          H        H6161      F7         NH         H          NH         H           H        H6162      F7         NH         H          NH         OH          H        H6163      F7         NH         H          NH         OA6         H        H6164      F7         NH         H          NH         OA8         H        H6165      F7         NH         H          NH         OA9         H        H6166      F7         NH         H          NH         OA10        H        H6167      F7         NH         H          NH         OA12        H        H6168      F7         NH         H          NH         OA14        H        H6169      F7         NH         H          NH         OA16        H        H6170      F7         NH         H          NH         OH          H        A66171      F7         NH         H          NH         OH          H        A86172      F7         NH         H          NH         OH          H        A96173      F7         NH         H          NH         OH          H        A106174      F7         NH         H          NH         OH          H        A126175      F7         NH         H          NH         OH          H        A146176      F7         NH         H          NH         OH          H        A166177      F7         NH         H          NH         OH          A6       A66178      F7         NH         H          NH         OH          A8       A86179      F7         NH         H          NH         OH          A10      A106180      F7         NH         H          NH         OA2         A2       A26181      F7         NH         H          NH         OA3         A3       A36182      F7         NH         H          NH         OA4         A4       A46183      F7         NH         H          NH         OC6         H        H6184      F7         NH         H          NH         OC7         H        H6185      F7         NH         H          NH         OC8         H        H6186      F7         NH         H          NH         OC10        H        H6187      F7         NH         H          NH         OC11        H        H6188      F7         NH         H          NH         OC12        H        H6189      F7         NH         H          NH         OC14        H        H6190      F7         NH         H          NH         OC16        H        H6191      F7         NH         H          NH         C6CO3      H        H6192      F7         NH         H          NH         C7CO3      H        H6193      F7         NH         H          NH         C8CO3      H        H6194      F7         NH         H          NH         C9CO3      H        H6195      F7         NH         H          NH         C1OCO3     H        H6196      F7         NH         H          NH         C12CO3     H        H6197      F7         NH         H          NH         C16CO3     H        H6198      F7         NH         C8         NH         OH          H        H6199      F7         NH         C9         NH         OH          H        H6200      F7         NH         C10        NH         OH          H        H6201      F7         NH         C12        NH         OH          H        H6202      F7         NH         C16        NH         OH          H        H6203      F7         NH         F1         NH         OH          H        H6204      F7         NH         F2         NH         OH          H        H6205      F7         NH         F3         NH         OH          H        H6206      F7         NH         F4         NH         OH          H        H6207      F7         NH         F5         NH         OH          H        H6208      F7         NH         F6         NH         OH          H        H6209      F7         NH         F7         NH         OH          H        H6210      F7         NH         F8         NH         OH          H        H6211      F7         NH         F9         NH         OH          H        H6212      F7         NH         F10        NH         OH          H        H6213      F7         NH         Ph         NH         OH          H        H6214      F7         NH         Bn         NH         OH          H        H6215      F7         NH         Pe         NH         OH          H        H6216      F7         NH         C12        NMe        OH          H        H6217      F7         NH         C12        NEt        OH          H        H6218      F7         NH         C12        NPr        OH          H        H6219      F7         NH         (CH2)3  N          OH          H        H6220      F7         NH         (CH2)4  N          OH          H        H6221      F7         NH         (CH2)5  N          OH          H        H6222      F7         NH         C12        O          OH          H        H6223      F7         NH         Ph         O          OH          H        H6224      F7         NH         C12        S          OH          H        H6225      F7         NH         Ph         S          OH          H        H6226      F7         NMe        H          NH         OH          H        H6227      F7         NEt        H          NH         OH          H        H6228      F7         NPr        H          NH         OH          H        H6229      F7         O          H          NH         OH          H        H6230      F7         S          H          NH         OH          H        H6231      F10        NH         H          NH         H           H        H6232      F10        NH         H          NH         OH          H        H6233      F10        NH         H          NH         OA6         H        H6234      F10        NH         H          NH         OA8         H        H6235      F10        NH         H          NH         OA9         H        H6236      F10        NH         H          NH         OA10        H        H6237      F10        NH         H          NH         OA12        H        H6238      F10        NH         H          NH         OA14        H        H6239      F10        NH         H          NH         OA16        H        H6240      F10        NH         H          NH         OH          H        A66241      F10        NH         H          NH         OH          H        A86242      F10        NH         H          NH         OH          H        A96243      F10        NH         H          NH         OH          H        A106244      F10        NH         H          NH         OH          H        A126245      F10        NH         H          NH         OH          H        A146246      F10        NH         H          NH         OH          H        A166247      F10        NH         H          NH         OH          A6       A66248      F10        NH         H          NH         OH          A8       A86249      F10        NH         H          NH         OH          A10      A106250      F10        NH         H          NH         OA2         A2       A26251      F10        NH         H          NH         OA3         A3       A36252      F10        NH         H          NH         OA4         A4       A46253      F10        NH         H          NH         OC6         H        H6254      F10        NH         H          NH         OC7         H        H6255      F10        NH         H          NH         OC8         H        H6256      F10        NH         H          NH         OC10        H        H6257      F10        NH         H          NH         OC11        H        H6258      F10        NH         H          NH         OC12        H        H6259      F10        NH         H          NH         OC14        H        H6260      F10        NH         H          NH         OC16        H        H6261      F10        NH         H          NH         C6CO3      H        H6262      F10        NH         H          NH         C7CO3      H        H6263      F10        NH         H          NH         C8CO3      H        H6264      F10        NH         H          NH         C9CO3      H        H6265      F10        NH         H          NH         C10CO3     H        H6266      F10        NH         H          NH         C12CO3     H        H6267      F10        NH         H           NH        C16CO3     H        H6268      F10        NH         C8          NH        OH          H        H6269      F10        NH         C9          NH        OH          H        H6270      F10        NH         C10         NH        OH          H        H6271      F10        NH         C12         NH        OH          H        H6272      F10        NH         C16         NH        OH          H        H6273      F10        NH         F1          NH        OH          H        H6274      F10        NH         F2          NH        OH          H        H6275      F10        NH         F3          NH        OH          H        H6276      F10        NH         F4          NH        OH          H        H6277      F10        NH         F5          NH        OH          H        H6278      F10        NH         F6          NH        OH          H        H6279      F10        NH         F7          NH        OH          H        H6280      F10        NH         F8          NH        OH          H        H6281      F10        NH         F9          NH        OH          H        H6282      F10        NH         F10         NH        OH          H        H6283      F10        NH         Ph          NH        OH          H        H6284      F10        NH         Bn          NH        OH          H        H6285      F10        NH         Pe          NH        OH          H        H6286      F10        NH         C12         NMe       OH          H        H6287      F10        NH         C12         NEt       OH          H        H6288      F10        NH         C12         NPr       OH          H        H6289      F10        NH         (CH2)3   N         OH          H        H6290      F10        NH         (CH2)4   N         OH          H        H6291      F10        NH         (CH2)5   N         OH          H        H6292      F10        NH         C12         O         OH          H        H6293      F10        NH         Ph          O         OH          H        H6294      F10        NH         C12         S         OH          H        H6295      F10        NH         Ph          S         OH          H        H6296      F10        HMe        H          NH         OH          H        H6297      F10        NEt        H          NH         OH          H        H6298      F10        NPr        H          NH         OH          H        H6299      F10        O          H          NH         OH          H        H6300      F10        S          H          NH         OH          H        H6301      Me         NH         H          NH         OH          H        H6302      Me         NH         H          NH         OA10        H        H6303      Me         NH         C12        NH         OH          H        H6304      Me         NH         F7         NH         OH          H        H6305      Me         NH         F9         NH         OH          H        H6306      Pr         NH         H          NH         OH          H        H6307      Pr         NH         H          NH         OA10        H        H6308      Pr         NH         C12        NH         OH          H        H6309      Pr         NH         F7         NH         OH          H        H6310      Pr         NH         F9         NH         OH          H        H6311      Bu         NH         H          NH         OH          H        H6312      Bu         NH         H          NH         OA10        H        H6313      Bu         NH         C12        NH         OH          H        H6314      Bu         NH         F7         NH         OH          H        H6315      Bu         NH         F9         NH         OH          H        H6316      Pen        NH         H          NH         OH          H        H6317      Pen        NH         H          NH         OA10        H        H6318      Pen        NH         C12        NH         OH          H        H6319      Pen        NH         F7         NH         OH          H        H6320      Pen        NH         F9         NH         OH          H        H6321      Hex        NH         H          NH         OH          H        H6322      Hex        NH         H          NH         OA10        H        H6323      Hex        NH         C12        NH         OH          H        H6324      Hex        NH         F7         NH         OH          H        H6325      Hex        NH         F9         NH         OH          H        H6326      Hep        NH         H          NH         OH          H        H6327      Hep        NH         H          NH         OA10        H        H6328      Hep        NH         C12        NH         OH          H        H6329      Hep        NH         F7         NH         OH          H        H6330      Hep        NH         F9         NH         OH          H        H6331      C8         NH         H          NH         OH          H        H6332      C8         NH         H          NH         OA10        H        H6333      C8         NH         C12        NH         OH          H        H6334      C8         NH         F7         NH         OH          H        H6335      C8         NH         F9         NH         OH          H        H6336      C9         NH         H          NH         OH          H        H6337      C9         NH         H          NH         OA10        H        H6338      C9         NH         C12        NH         OH          H        H6339      C9         NH         F7         NH         OH          H        H6340      C9         NH         F9         NH         OH          H        H6341      C10        NH         H          NH         OH          H        H6342      C10        NH         H          NH         OA10        H        H6343      C10        NH         C12        NH         OH          H        H6344      C10        NH         F7         NH         OH          H        H6345      C10        NH         F9         NH         OH          H        H6346      C11        NH         H          NH         OH          H        H6347      C11        NH         H          NH         OA10        H        H6348      C11        NH         C12        NH         OH          H        H6349      C11        NH         F7         NH         OH          H        H6350      C11        NH         F9         NH         OH          H        H6351      C12        NH         H          NH         OH          H        H6352      C12        NH         H          NH         OA10        H        H6353      C12        NH         C12        NH         OH          H        H6354      C12            NH         F7         NH         OH          H        H6355      C12            NH         F9         NH         OH          H        H6356      C14            NH         H          NH         OH          H        H6357      C14            NH         H          NH         OA10        H        H6358      C14            NH         C12        NH         OH          H        H6359      C14            NH         F7         NH         OH          H        H6360      C14            NH         F9         NH         OH          H        H6361      C16            NH         H          NH         OH          H        H6362      C16            NH         H          NH         OA10        H        H6363      C16            NH         C12        NH         OH          H        H6364      C16            NH         F7         NH         OH          H        H6365      C16            NH         F9         NH         OH          H        H6366      C18            NH         H          NH         OH          H        H6367      C18            NH         H          NH         OA10        H        H6368      C18            NH         C12        NH         OH          H        H6369      C18            NH         F7         NH         OH          H        H6370      C18            NH         F9         NH         OH          H        H6371      2-Et-Hex       NH         H          NH         OH          H        H6372      2-Et-Hex       NH         H          NH         OA10        H        H6373      2-Et-Hex       NH         C12        NH         OH          H        H6374      2-Et-Hex       NH         F7         NH         OH          H        H6375      2-Et-Hex       NH         F9         NH         OH          H        H6376      cHex           NH         H          NH         OH          H        H6377      cHex           NH         H          NH         OA10        H        H6378      cHex           NH         C12        NH         OH          H        H6379      cHex           NH         F7         NH         OH          H        H6380      cHex           NH         F9         NH         OH          H        H6381      4-tBu-cHex     NH         H          NH         OH          H        H6382      4-tBu-cHex     NH         H          NH         OA10        H        H6383      4-tBu-cHex      NH      C12       NH        OH          H        H6384      4-tBu-cHex      NH      F7        NH        OH          H        H6385      4-tBu-cHex      NH      F9        NH        OH          H        H6386      cycloheptyl     NH      H         NH        OH          H        H6387      cycloheptyl     NH      H         NH        OA10        H        H6388      cycloheptyl     NH      C12       NH        OH          H        H6389      cycloheptyl     NH      F7        NH        OH          H        H6390      cycloheptyl     NH      F9        NH        OH          H        H6391      cyclooctyl      NH      H         NH        OH          H        H6392      cyclooctyl      NH      H         NH        OA10        H        H6393      cyclooctyl      NH      C12       NH        OH          H        H6394      cyclooctyl      NH      F7        NH        OH          H        H6395      cyclooctyl      NH      F9        NH        OH          H        H6396      cyclododecyl    NH      H         NH        OH          H        H6397      cyclododecyl    NH      H         NH        OA10        H        H6398      cyclododecyl    NH      C12       NH        OH          H        H6399      cyclododecyl    NH      F7        NH        OH          H        H6400      cyclododecyl    NH      F9        NH        OH          H        H6401      cHex-CH2       NH      H         NH        OH          H        H6402      cHex-CH2       NH      H         NH        OA10        H        H6403      cHex-CH2       NH      C12       NH        OH          H        H6404      cHex-CH2       NH      F7        NH        OH          H        H6405      cHex-CH2       NH      F9        NH        OH          H        H6406      CHE             NH      H         NH        OH          H        H6407      CHE             NH      H         NH        OA10        H        H6408      CHE             NH      C12       NH        OH          H        H6409      CHE             NH      F7        NH        OH          H        H6410      CHE             NH      F9        NH        OH          H        H6411      COD             NH      H         NH        OH          H        H6412      COD                   NH         H          NH        OA10       H       H6413      COD                   NH         C12        NH        OH         H       H6414      COD                   NH         F7         NH        OH         H       H6415      COD                   NH         F9         NH        OH         H       H6416      3-EtO-Pr              NH         H          NH        OH         H       H6417      3-EtO-Pr              NH         H          NH        OA10       H       H6418      3-EtO-Pr              NH         C12        NH        OH         H       H6419      3-EtO-Pr              NH         F7         NH        OH         H       H6420      3-EtO-Pr              NH         F9         NH        OH         H       H6421      3-MeS-Pr              NH         H          NH        OH         H       H6422      3-MeS-Pr              NH         H          NH        OA10       H       H6423      3-MeS-Pr              NH         C12        NH        OH         H       H6424      3-MeS-Pr              NH         F7         NH        OH         H       H6425      3-MeS-Pr              NH         F9         NH        OH         H       H6426      2,2-(MeO)2-Et       NH         H          NH        OH         H       H6427      2,2-(MeO)2-Et       NH         H          NH        OA10       H       H6428      2,2-(MeO)2-Et       NH         C12        NH        OH         H       H6429      2,2-(MeO)2-Et       NH         F7         NH        OH         H       H6430      2,2-(MeO)2-Et       NH         F9         NH        OH         H       H6431      2,2-(EtO)2-Et       NH         H          NH        OH         H       H6432      2,2-(EtO)2-Et       NH         H          NH        OA10       H       H6433      2,2-(EtO)2-Et       NH         C12        NH        OH         H       H6434      2,2-(EtO)2-Et       NH         F7         NH        OH         H       H6435      2,2-(EtO)2-Et       NH         F9         NH        OH         H       H6436      2-OH-Et               NH         H          NH        OH         H       H6437      2-OH-Et               NH         H          NH        OA10       H       H6438      2-OH-Et               NH         C12        NH        OH         H       H6439      2-OH-Et               NH         F7         NH        OH         H       H6440      2-OH-Et               NH         F9         NH        OH         H       H6441      2-NH2-Et          NH          H           NH          OH          H       H6442      2-NH2-Et          NH          H           NH          OA10        H       H6443      2-NH2-Et          NH          C12         NH          OH          H       H6444      2-NH2-Et          NH          F7          NH          OH          H       H6445      2-NH2-Et          NH          F9          NH          OH          H       H6446      4-OH-Bu            NH          H           NH          OH          H       H6447      4-OH-Bu            NH          H           NH          OA10        H       H6448      4-OH-Bu            NH          C12         NH          OH          H       H6449      4-OH-Bu            NH          F7          NH          OH          H       H6450      4-OH-Bu            NH          F9          NH          OH          H       H6451      5-OH-Pen           NH          H           NH          OH          H       H6452      5-OH-Pen           NH          H           NH          OA10        H       H6453      5-OH-Pen           NH          C12         NH          OH          H       H6454      5-OH-Pen           NH          F7          NH          OH          H       H6455      5-OH-Pen           NH          F9          NH          OH          H       H6456      Pe                 NH          H           NH          OH          H       H6457      Pe                 NH          H           NH          OA10        H       H6458      Pe                 NH          C12         NH          OH          H       H6459      Pe                 NH          F7          NH          OH          H       H6460      Pe                 NH          F9          NH          OH          H       H6461      4-Me-Pe            NH          H           NH          OH          H       H6462      4-Me-Pe            NH          H           NH          OA10        H       H6463      4-Me-Pe            NH          C12         NH          OH          H       H6464      4-Me-Pe            NH          F7          NH          OH          H       H6465      4-Me-Pe            NH          F9          NH          OH          H       H6466      2-MeO-Pe           NH          H           NH          OH          H       H6467      2-MeO-Pe           NH          H           NH          OA10        H       H6468      2-MeO-Pe           NH          C12         NH          OH          H       H6469      2-MeO-Pe           NH          F7          NH          OH          H       H6470      2-MeO-Pe           NH          F9          NH          OH          H       H6471      3-MeO-Pe           NH          H           NH          OH          H       H6472      3-MeO-Pe           NH          H           NH          OA10        H       H6473      3-MeO-Pe           NH          C12         NH          OH          H       H6474      3-MeO-Pe           NH          F7          NH          OH          H       H6475      3-MeO-Pe           NH          F9          NH          OH          H       H6476      4-MeO-Pe           NH          H           NH          OH          H       H6477      4-MeO-Pe           NH          H           NH          OA10        H       H6478      4-MeO-Pe           NH          C12         NH          OH          H       H6479      4-MeO-Pe           NH          F7          NH          OH          H       H6480      4-MeO-Pe           NH          F9          NH          OH          H       H6481      3,4-(MeO)2-Pe    NH          H           NH          OH          H       H6482      3,4-(MeO)2-Pe    NH          H           NH          OA10        H       H6483      3,4-(MeO)2-Pe    NH          C12         NH          OH          H       H6484      3,4-(MeO)2-Pe    NH          F7          NH          OH          H       H6485      3,4-(MeO)2-Pe    NH          F9          NH          OH          H       H6486      4-F-Pe             NH          H           NH          OH          H       H6487      4-F-Pe             NH          H           NH          OA10        H       H6488      4-F-Pe             NH          C12         NH          OH          H       H6489      4-F-Pe             NH          F7          NH          OH          H       H6490      4-F-Pe             NH          F9          NH          OH          H       H6491      2-Cl-Pe            NH          H           NH          OH          H       H6492      2-Cl-Pe            NH          H           NH          OA10        H       H6493      2-Cl-Pe            NH          C12         NH          OH          H       H6494      2-Cl-Pe            NH          F7          NH          OH          H       H6495      2-Cl-Pe            NH          F9          NH          OH          H       H6496      3-Cl-Pe            NH          H           NH          OH          H       H6497      3-Cl-Pe            NH          H           NH          OA10        H       H6498      3-Cl-Pe            NH          C12         NH          OH          H       H6499      3-Cl-Pe            NH          F7          NH          OH          H       H6500      3-Cl-Pe            NH          F9          NH          OH          H       H6501      4-Cl-Pe            NH          H           NH          OH          H       H6502      4-Cl-Pe            NH          H           NH          OA10        H       H6503      4-Cl-Pe            NH          C12         NH          OH          H       H6504      4-Cl-Pe            NH          F7          NH          OH          H       H6505      4-Cl-Pe            NH          F9          NH          OH          H       H6506      2,4-Cl2-Pe       NH          H           NH          OH          H       H6507      2,4-Cl2-Pe       NH          H           NH          OA10        H       H6508      2,4-Cl2-Pe       NH          C12         NH          OH          H       H6509      2,4-Cl2-Pe       NH          F7          NH          OH          H       H6510      2,4-Cl2-Pe       NH          F9          NH          OH          H       H6511      4-OH-Pe            NH          H           NH          OH          H       H6512      4-OH-Pe            NH          H           NH          OA10        H       H6513      4-OH-Pe            NH          C12         NH          OH          H       H6514      4-OH-Pe            NH          F7          NH          OH          H       H6515      4-OH-Pe            NH          F9          NH          OH          H       H6516      2,2-Ph2-Et       NH          H           NH          OH          H       H6517      2,2-Ph2-Et       NH          H           NH          OA10        H       H6518      2,2-Ph2-Et       NH          C12         NH          OH          H       H6519      2,2-Ph2-Et       NH          F7          NH          OH          H       H6520      2,2-Ph2-Et       NH          F9          NH          OH          H       H6521      2-(2-Py)-Et        NH          H           NH          OH          H       H6522      2-(2-Py)-Et        NH          H           NH          OA10        H       H6523      2-(2-Py)-Et        NH          C12         NH          OH          H       H6524      2-(2-Py)-Et        NH          F7          NH          OH          H       H6525      2-(2-Py)-Et        NH          F9          NH          OH          H       H6526      2-(2-Tp)-Et        NH          H           NH          OH          H       H6527      2-(2-Tp)-Et        NH          H           NH          OA10        H       H6528      2-(2-Tp)-Et        NH          C12         NH          OH          H       H6529      2-(2-Tp)-Et        NH          F7          NH          OH          H       H6530      2-(2-Tp)-Et        NH          F9          NH          OH          H       H6531      Bn                 NH          H           NH          OH          H       H6532      Bn                 NH          H           NH          OA10        H       H6533      Bn                 NH          C12         NH          OH          H       H6534      Bn                 NH          F7          NH          OH          H       H6535      Bn                 NH          F9          NH          OH          H       H6536      2-Me-Bn            NH          H           NH          OH          H       H6537      2-Me-Bn            NH          H           NH          OA10        H       H6538      2-Me-Bn            NH          C12         NH          OH          H       H6539      2-Me-Bn            NH          F7          NH          OH          H       H6540      2-Me-Bn            NH          F9          NH          OH          H       H6541      4-Me-Bn            NH          H           NH          OH          H       H6542      4-Me-Bn            NH          H           NH          OA10        H       H6543      4-Me-Bn            NH          C12         NH          OH          H       H6544      4-Me-Bn            NH          F7          NH          OH          H       H6545      4-Me-Bn            NH          F9          NH          OH          H       H6546      4-F-Bn             NH          H           NH          OH          H       H6547      4-F-Bn             NH          H           NH          OA10        H       H6548      4-F-Bn             NH          C12         NH          OH          H       H6549      4-F-Bn             NH          F7          NH          OH          H       H6550      4-F-Bn             NH          F9          NH          OH          H       H6551      2-MeO-Bn           NH          H           NH          OH          H       H6552      2-MeO-Bn           NH          H           NH          OA10        H       H6553      2-MeO-Bn           NH          C12         NH          OH          H       H6554      2-MeO-Bn           NH          F7          NH          OH          H       H6555      2-MeO-Bn           NH          F9          NH          OH          H       H6556      4-MeO-Bn           NH          H           NH          OH          H       H6557      4-MeO-Bn           NH          H           NH          OA10        H       H6558      4-MeO-Bn           NH          C12         NH          OH          H       H6559      4-MeO-Bn           NH          F7          NH          OH          H       H6560      4-MeO-Bn           NH          F9          NH          OH          H       H6561      3,4,5-(MeO)3-Bn NH          H           NH          OH          H       H6562      3,4,5-(MeO)3-Bn NH          H           NH          OA10        H       H6563      3,4,5-(MeO)3-Bn NH          C12         NH          OH          H       H6564      3,4,5-(MeO)3-Bn NH          F7          NH          OH          H       H6565      3,4,5-(MeO)3-Bn NH          F9          NH          OH          H       H6566      3,4-OCH2O-Bn     NH          H           NH          OH          H       H6567      3,4-OCH2O-Bn     NH          H           NH          OA10        H       H6568      3,4-OCH2O-Bn     NH          C12         NH          OH          H       H6569      3,4-OCH2O-Bn     NH          F7          NH          OH          H       H6570      3,4-OCH2O-Bn     NH          F9          NH          OH          H       H6571      1-Ph-Et            NH          H           NH          OH          H       H6572      1-Ph-Et            NH          H           NH          OA10        H       H6573      1-Ph-Et            NH          C12         NH          OH          H       H6574      1-Ph-Et            NH          F7          NH          OH          H       H6575      1-Ph-Et            NH          F9          NH          OH          H       H6576      2-Nap-CH2         NH          H           NH          OH          H       H6577      2-Nap-CH2         NH          H           NH          OA10        H       H6578      2-Nap-CH2         NH          C12         NH          OH          H       H6579      2-Nap-CH2         NH          F7          NH          OH          H       H6580      2-Nap-CH2         NH          F9          NH          OH          H       H6581      2-Fu-CH2          NH          H           NH          OH          H       H6582      2-Fu-CH2          NH          H           NH          OA10        H       H6583      2-Fu-CH2          NH          C12         NH          OH          H       H6584      2-Fu-CH2          NH          F7          NH          OH          H       H6585      2-Fu-CH2          NH          F9          NH          OH          H       H6586      2-Tp-CH2          NH          H           NH         OH           H       H6587      2-Tp-CH2          NH          H           NH         OA10         H       H6588      2-Tp-CH2          NH          C12         NH         OH           H       H6589      2-Tp-CH2          NH          F7          NH         OH           H       H6590      2-Tp-CH2          NH          F9          NH         OH           H       H6591      2-Py-CH2          NH          H           NH         OH           H       H6592      2-Py-CH2          NH          H           NH         OA10         H       H6593      2-Py-CH2          NH          C12         NH         OH           H       H6594      2-Py-CH2          NH          F7          NH         OH           H       H6595      2-Py-CH2          NH          F9          NH         OH           H       H6596      2-Ta               NH          H           NH         OH           H       H6597      2-Ta               NH          H           NH         OA10         H       H6598      2-Ta               NH          C12         NH         OH           H       H6599      2-Ta               NH          F7          NH         OH           H       H6600      2-Ta               NH          F9          NH         OH           H       H6601      2-DHT              NH          H           NH         OH           H       H6602      2-DHT              NH          H           NH         OA10         H       H6603      2-DHT              NH          C12         NH         OH           H       H6604      2-DHT              NH          F7          NH         OH           H       H6605      2-DHT              NH          F9          NH         OH           H       H6606      2-CTD              NH          H           NH         OH           H       H6607      2-CTD              NH          H           NH         OA10         H       H6608      2-CTD              NH          C12         NH         OH           H       H6609      2-CTD              NH          F7          NH         OH           H       H6610      2-CTD              NH          F9          NH         OH           H       H6611      2-Qin              NH          H           NH         OH           H       H6612      2-Qin              NH          H           NH         OA10         H       H6613      2-Qin              NH          C12         NH         OH           H       H6614      2-Qin              NH          F7          NH         OH           H       H6615      2-Qin              NH          F9          NH          OH          H       H6616      6-DTP              NH          H           NH          OH          H       H6617      6-DTP              NH          H           NH          OA10        H       H6618      6-DTP              NH          C12         NH          OH          H       H6619      6-DTP              NH          F7          NH          OH          H       H6620      6-DTP              NH          F9          NH          OH          H       H6621      (CH2)4          N           H           NH          OH          H       H6622      (CH2)4          N           H           NH          OA10        H       H6623      (CH2)4          N           C12         NH          OH          H       H6624      (CH2)4          N           F7          NH          OH          H       H6625      (CH2)4          N           F9          NH          OH          H       H6626      Bu                 NMe         H           NH          OH          H       H6627      3-Ph-Pr            NH          H           NH          OH          H       H6628      3,3-Ph2-Pr       NH          H           NH          OH          H       H6629      2-Ph-Et            O           H           NH          OH          H       H6630      cHex               O           H           NH          OH          H       H6631      Ph                 NH          H           NH          OA7         H       H[表2]
Figure A0081465302751
化合物编号        R1            R2      R3       R6       R7       R126632        3-NH2-Ph      H         H         H         H         H6633        3-NH2-Ph      H         OH        H         H         H6634        3-NH2-Ph      H         OA6       H         H         H6635        3-NH2-Ph      H         OA8       H         H         H6636        3-NH2-Ph      H         OA9       H         H         H6637        3-NH2-Ph      H         OA10      H         H         H6638        3-NH2-Ph      H         OA12      H         H         H6639        3-NH2-Ph      H         OA14      H         H         H6640        3-NH2-Ph      H         OA16      H         H         H6641        3-NH2-Ph      H         OH        H         A6        H6642        3-NH2-Ph      H         OH        H         A8        H6643        3-NH2-Ph      H         OH        H         A9        H6644        3-NH2-Ph      H         OH        H         A10       H6645        3-NH2-Ph      H         OH        H         A12       H6646        3-NH2-Ph      H         OH        H         A14       H6647        3-NH2-Ph      H         OH        H         A16       H6648        3-NH2-Ph      H         OH        A6        A6        H6649        3-NH2-Ph      H         OH        A8        A8        H6650        3-NH2-Ph      H         OH        A10       A10       H6651        3-NH2-Ph      C8        OH        H         H         H6652        3-NH2-Ph      C9        OH        H         H         H6653        3-NH2-Ph      C10       OH        H         H         H6654        3-NH2-Ph      C12       OH        H         H         H6655        3-NH2-Ph      C16       OH        H         H         H6656        3-NH2-Ph      H         OC6       H         H         H6657        3-NH2-Ph      H         OC7       H         H         H6658        3-NH2-Ph      H         OC8       H         H         H6659        3-NH2-Ph      H         OC10      H         H         H6660        3-NH2-Ph      H         OC11      H         H         H6661        3-NH2-Ph      H         OC12      H         H         H6662        3-NH2-Ph      H         OC14      H         H         H6663        3-NH2-Ph      H         OC16      H         H         H6664        4-Me2N-Ph     H         H         H         H         H6665        4-Me2N-Ph     H         OH        H         H         H6666        4-Me2N-Ph     H         OA6       H         H         H6667        4-Me2N-Ph     H         OA8       H         H         H6668        4-Me2N-Ph     H         OA9       H         H         H6669        4-Me2N-Ph     H         OA10      H         H         H6670        4-Me2N-Ph     H         OA12      H         H         H6671        4-Me2N-Ph     H         OA14      H         H         H6672        4-Me2N-Ph     H         OA16      H         H         H6673        4-Me2N-Ph     H         OH        H         A6        H6674        4-Me2N-Ph     H         OH        H         A8        H6675        4-Me2N-Ph     H         OH        H         A9        H6676        4-Me2N-Ph     H         OH        H         A10       H6677        4-Me2N-Ph     H         OH        H         A12       H6678        4-Me2N-Ph     H         OH        H         A14       H6679        4-Me2N-Ph     H         OH        H         A16       H6680        4-Me2N-Ph     H         OH        A6        A6        H6681        4-Me2N-Ph     H         OH        A8        A8        H6682        4-Me2N-Ph     H         OH        A10       A10       H6683        4-Me2N-Ph     C8        OH        H         H         H6684        4-Me2N-Ph     C9        OH        H         H         H6685        4-Me2N-Ph     C10       OH        H         H         H6686        4-Me2N-Ph     C12       OH        H         H         H6687        4-Me2N-Ph     C16       OH        H         H         H6688        4-Me2N-Ph     H         OC6       H         H         H6689        4-Me2N-Ph     H         OC7       H         H         H6690        4-Me2N-Ph     H         OC8       H         H         H6691        4-Me2N-Ph     H         OC10      H         H         H6692        4-Me2N-Ph     H         OC11      H         H         H6693        4-Me2N-Ph     H         OC12      H         H         H6694        4-Me2N-Ph     H         OC14      H         H         H6695        4-Me2N-Ph     H         OC16      H         H         H6696        Ph             H         OH        H         H         POM6697        Ph             H         OH        H         H         ECE6698        Ph             H         OH        H         H         HCE6699        Ph             H         OH        H         H         DCE6700        Ph             H         OH        H         H         CCE6701        Ph             H         OH        H         H         HOE6702        3,4-F2-Ph    H         OH        H         H         POM6703        3,4-F2-Ph    H         OH        H         H         ECE6704        3,4-F2-Ph    H         OH        H         H         HCE6705        3,4-F2-Ph    H         OH        H         H         DCE6706        3,4-F2-Ph    H         OH        H         H         CCE6707        3,4-F2-Ph    H         OH        H         H         HOE6708        4-Bu-Ph       H         OH        H         H         POM6709        4-Bu-Ph       H         OH        H         H         ECE6710        4-Bu-Ph       H         OH        H         H         HCE6711        4-Bu-Ph       H         OH        H         H         DCE6712        4-Bu-Ph       H         OH        H         H         CCE6713        4-Bu-Ph       H         OH        H         H         HOE6714        4-NO2-Ph     H         OH        H         H         POM6715        4-NO2-Ph     H         OH        H         H         ECE6716        4-NO2-Ph     H         OH        H         H         HCE6717        4-NO2-Ph     H         OH        H         H         DCE6718        4-NO2-Ph     H         OH        H         H         CCE6719        4-NO2-Ph     H         OH        H         H         HOE6720        4-F-Ph        H         OH        H         H         POM6721        4-F-Ph        H         OH        H         H         ECE6722        4-F-Ph        H         OH        H         H         HCE6723        4-F-Ph        H         OH        H         H         DCE6724        4-F-Ph        H         OH        H         H         CCE6725        4-F-Ph        H         OH        H         H         HOE[表3]化合物编号          X1       m         n6726          NH        0         16727          NH        0         26728          NH        0         36729          NH        0         46730          NH        0         56731          NH        0         66732          NH        0         76733          NH        0         86734          NH        0         96735          NH        0         106736          NH        0         116737          O         0         16738          O         0         26739          O         0         36740          O         0         46741          O         0         56742          O         0         66743          O         0         76744          O         0         86745          O         0         96746          O         0         106747          O         0         116748          NH        2         16749          NH        2         26750          NH        2         36751          NH        2         46752          NH        2         56753          NH        2         66754          NH        2         76755          NH        2         86756          NH        2         96757          NH        2         106758          NH        2         116759          O         2         16760          O         2         26761          O         2         36762          O         2         46763          O         2         56764          O         2         66765          O         2         76766          O         2         86767          O         2         96768          O         2         106769          O         2         11条件是,Me表示甲基Et表示乙基、Pr表示丙基、iPr表示异丙基、Bu表示丁基、tBu表示叔丁基、sBu表示仲丁基、Pen表示戊基、Hex表示己基、cHex表示环己基、Hep表示庚基、Vin表示乙烯基、Ph表示苯基、Bn表示苄基、Pe表示苯乙基、Nap表示萘基、C8和Oct表示辛基、C9表示壬基、C10和Dec表示癸基、C11表示十一烷基、C12表示十二烷基、C14表示十四烷基、C16表示十六烷基、C18表示十八烷基、OC6表示己氧基、OC7表示庚氧基、OC8表示辛氧基、OC10表示癸氧基、OC12表示十二烷氧基、C6CO3表示己氧羰基氧基、C7CO3表示庚氧羰基氧基、C8CO3表示辛氧羰基氧基、C9CO3表示壬氧羰基氧基、C10CO3表示癸氧羰基氧基、C12CO3表示十二烷氧羰基氧基、C16CO3表示十六烷氧羰基氧基、A2表示乙酰基、A3表示丙酰基、A4表示丁酰基、A6表示己酰基、A8表示辛酰基、A9表示壬酰基、A10表示癸酰基、A12表示十二烷酰基、A14表示十四烷酰基、A16表示十六烷酰基、OA2表示乙酰氧基、OA3表示丙酰氧基、OA4表示丁酰氧基、OA6表示己酰氧基、OA8表示辛酰氧基、OA9表示壬酰氧基、OA10表示癸酰氧基、OA12表示十二烷酰氧基、OA14表示十四烷酰氧基、OA16表示十六烷酰氧基、F1表示H(CF2)2CH2所示基团、F2表示CF3CF2CH2所示基团、F3表示CF3(CF2)2CH2所示基团、F4表示CF3(CF2)5CH2所示基团、F5表示CF3(CF2)6CH2所示基团、F6表示CF3(CF2)7CH2所示基团、F7表示CF3(CF2)3CH2CH2所示基团、F8表示CF3(CF2)5CH2CH2所示基团、F9表示CF3(CF2)7CH2CH2所示基团、F10表示CF3(CF2)9CH2CH2所示基团、F11表示FCH2CH2所示基团、F12表示FCH2CH2CH2CH2所示基团、Mor表示吗啉代基、PA表示苯基偶氮基、CHE表示2-(1-环己烯)乙基、COD表示顺式-十八-9-烯基、Py表示吡啶基、Tp表示苯硫基、Fu表示呋喃基、Ta表示噻唑基、DHT表示4,5-二氢噻唑基、CTD表示5-环丙基-1,3,4-噻二唑基、Qin表示喹啉基、DTP表示4H-1,2-二硫代-4,3-b-5-酮-吡咯基、POM表示新戊酰氧甲基、ECE表示1-(乙氧羰基氧)乙基、HCE表示1-(己氧羰基氧)乙基、DCE表示1-(癸氧羰基氧)乙基、CCE表示1-(环己氧羰基氧)乙基、HOE表示1-(己酰氧)乙基。
上表1~3中的优选化合物是,化合物编号1至420、491至1120、1401至1540、1611至1748、1961至2520、2591至2870、2941至3430、3711至3850、4131至5460、5531至5670、5741至6090、和6631的化合物。
更优选的化合物是,化合物编号2至55、72至125、142至195、212至265、282至335、352至405、492至545、562至615、632至685、702至755、772至825、842至895、912至965、982至1035、1052至1l05、1402至1455、1472至1525、1612至1665、1682至1735、1962至2015、2032至2085、2102至2155、2172至2225、2242至2295、2312至2365、2382至2435、2452至2505、2592至2645、2662至2715、2732至2785、2802至2855、2942至2995、3012至3065、3082至3135、3152至3205、3222至3275、3292至3345、3362至3415、3712至3765、3782至3835、4132至4185、4202至4255、4272至4325、4342至4395、4412至4465、4482至4535、4552至4605、4622至4675、4692至4745、4762至4815、4832至4885、4902至4955、4972至5025、5042至5095、5112至5165、5182至5235、5252至5305、5322至5375、5392至5445、5532至5585、5602至5655、5742至5795、5812至5865、5882至5935、5952至6005、6022至6075、和6631的化合物。
更优选的化合物是,化合物编号2至9、72至79、142至149、212至219、282至389、352至459、492至599、562至569、632至639、702至709、772至779、842至849、912至919、982至989、1052至1059、1402至1409、1472至1479、1612至1619、1682至1689、1962至1969、2032至2039、2102至2109、2172至2179、2242至2249、2312至2319、2382至2389、2452至2459、2592至2599、2662至2669、2732至2739、2802至2809、2942至2949、3012至3019、3082至3089、3152至3159、3222至3229、3292至3299、3362至3369、3712至3719、3782至3789、4132至4139、4202至4209、4272至4279、4342至4349、4412至4419、4482至4489、4552至4559、4622至4629、4692至4699、4762至4769、4832至4839、4902至4909、4972至4979、5042至5049、5112至5119、5182至5189、5252至5259、5322至5329、5392至5399、5532至5539、5602至5609、5742至5749、5812至5819、5882至5889、5952至5959、6022至6029、和6631的化合物。特别优选的化合物是,化合物编号2至9、142至149、562至569、982至989、1472至1479、2242至2249、2312至2319、2382至2389、3012至3019、3712至3719、4132至4139、4202至4209、4762至4769、4832至4839、5532至5539的化合物。最优选的化合物是,化合物编号2、6、142、146、562、982、1472、1476、2242、2312、2382、3012、3016、3712、3716、4132、4136、4202、4206、4762、4766、4832、4836、5532和5536的化合物。
通式(I’)中特别优选,
R1表示苯基、R2表示氢原子、X1和X2表示式-NH-所示基团、R3表示羟基的化合物(化合物编号2、实施例43),
R1表示苯基、R2表示氢原子、X1和X2表示式-NH-所示基团、R3表示癸酰氧基的化合物(化合物编号6、实施例81),
R1表示4-乙基苯基、R2表示氢原子、X1和X2表示式-NH-所示基团、R3表示羟基的化合物(化合物编号142、实施例44),
R1表示4-乙基苯基、R2表示氢原子、X1和X2表示式-NH-所示基团、R3表示癸酰氧基的化合物(化合物编号146),
R1表示4-戊基苯基、R2表示氢原子、X1和X2表示式-NH-所示基团、R3表示羟基的化合物(化合物编号562、实施例55),
R1表示3-乙基苯基、R2表示氢原子、X1和X2表示式-NH-所示基团、R3表示羟基的化合物(化合物编号982、实施例58),
R1表示4-三氟甲基苯基、R2表示氢原子、X1和X2表示式-NH-所示基团、R3表示羟基的化合物(化合物编号1472、实施例50),
R1表示4-三氟甲基苯基、R2表示氢原子、X1和X2表示式-NH-所示基团、R3表示癸酰氧基的化合物(化合物编号1476),
R1表示4-丁氧苯基、R2表示氢原子、X1和X2表示式-NH-所示基团、R3表示羟基的化合物(化合物编号2242、实施例62),
R1表示4-戊氧苯基、R2表示氢原子、X1和X2表示式-NH-所示基团、R3表示羟基的化合物(化合物编号2312、实施例64),
R1表示4-己氧苯基、R2表示氢原子、X1和X2表示式-NH-所示基团、R3表示羟基的化合物(化合物编号2832、实施例63),
R1表示4-氟苯基、R2表示氢原子、X1和X2表示式-NH-所示基团、R3表示羟基的化合物(化合物编号3012、实施例45),
R1表示4-氟苯基、R2表示氢原子、X1和X2表示式-NH-所示基团、R3表示癸酰氧基的化合物(化合物编号3016),
R1表示3,4-二氟苯基、R2表示氢原子、X1和X2表示式-NH-所示基团、R3表示羟基的化合物(化合物编号3712,实施例57),
R1表示3,4-二氟苯基、R2表示氢原子、X1和X2表示式-NH-所示基团、R3表示癸酰氧基的化合物(化合物编号3716),
R1表示3-氯-4-氟苯基、R2表示氢原子、X1和X2表示式-NH-所示基团、R3表示羟基的化合物(化合物编号4132、实施例60),
R1表示3-氯-4-氟苯基、R2表示氢原子、X1和X2表示式-NH-所示基团、R3表示癸酰氧基的化合物(化合物编号4136),
R1表示3-三氟甲基-4-氟苯基、R2表示氢原子、X1和X2表示式-NH-所示基团、R3表示羟基的化合物(化合物编号4202、实施例65),
R1表示3-三氟甲基-4-氟苯基、R2表示氢原子、X1和X2表示式-NH-所示基团、R3表示癸酰氧基的化合物(化合物编号4206),
R1表示3-甲基-4-溴苯基、R2表示氢原子、X1和X2表示式-NH-所示基团、R3表示羟基的化合物(化合物编号4762、实施例96),
R1表示3-甲基-4-溴苯基、R2表示氢原子、X1和X2表示式-NH-所示基团、R3表示癸酰氧基的化合物(化合物编号4766),
R1表示3-硝基-4-氟苯基、R2表示氢原子、X1和X2表示式-NH-所示基团、R3表示羟基的化合物(化合物编号4832、实施例97),
R1表示3-硝基-4-氟苯基、R2表示氢原子、X1和X2表示式-NH-所示基团、R3表示癸酰氧基的化合物(化合物编号4836),
R1表示3-硝基苯基、R2表示氢原子、X1和X2表示式-NH-所示基团、R3表示羟基的化合物(化合物编号5532、实施例95),
R1表示3-硝基苯基、R2表示氢原子、X1和X2表示式-NH-所示基团、R3表示癸酰氧基的化合物(化合物编号5536)。
本发明的具有通式(I)的化合物、其药理上可接受的醚、酯和N-烷基衍生物,可使用下面A至H法,或通过适当组合这些方法中使用的步骤制备。
[A法]
A法是制造通式(I)中R1-X1是式R1R4N-所示基团、R2-X2是氨基、R3是羟基的化合物(Ia)的方法。
A法
上述式中,R1和R4与前述定义相同。
第A1工序是从化合物(VI)制备化合物(Ia)的工序。该工序可通过使化合物(VI)在溶剂中与式R1R4NH所示的化合物反应而完成。
作为起始原料的化合物(VI),可从后述的微生物生产物中分离。
所使用的式R1R4NH所示的化合物是,具有所需的R1和R4,充分的亲核性的氨基化合物,优选伯烷基胺类和环胺类。对于不具有充分亲核性的化合物,使用下述B法反应。
所使用的溶剂,只要是不抑制反应,可以一定程度溶解起始原料和反应试剂的都可以,对此没有特别的限制,可列举例如,甲醇、乙醇等醇类;N,N-二甲基甲酰胺、N,N-二甲基乙酰胺等酰胺类,但是优选醇类(特别是甲醇)。
反应温度根据所使用的胺和溶剂等变化,但是通常为0℃~150℃,优选20℃~100℃。
反应时间根据反应温度等变化,但是通常在30分钟~2天,优选5小时~1天。
反应完成后,本反应的目的产物可按照常规方法从反应混合物中分离出来。例如,将反应混合物适当中和,或在存在不溶物时通过过滤除去不溶物后,减压蒸除溶剂,加入乙酸乙酯或二氯甲烷等与水不混溶的有机溶剂,用稀盐酸水溶液、碳酸氢钠水溶液、氯化钠水溶液等适当洗涤,用无水硫酸镁干燥后,蒸除溶剂得到,如果需要,可通过常规方法,例如重结晶、再沉淀或色谱法进行纯化精制。
所得化合物(Ia),根据需要,通过后述方法,可转化为其中R3是氢原子的化合物或其醚或酯衍生物。
[B法]
B法是通式(I)中R2-X2是氨基、R3是羟基的化合物(Ib)的制备方法。
B法
Figure A0081465302891
上述式中,R1和X1定义同前,Rp可相同或不同,表示氢原子、碳原子数1~3的烷基、或与Rp结合的碳原子一起形成5或6元环烷基的基团。
第B1工序是从化合物(VI)制备化合物(B1)的工序。该工序可通过使化合物(VI)在溶剂中在酸催化剂存在下与缩醛化试剂反应完成。
关于起始原料的化合物(VI)的制备方法在后面叙述。
使用的缩醛化试剂是式(Rp)2C=O所示化合物或其等价体。可列举例如,甲醛、乙醛、丙酮、甲基乙基酮、二乙基酮、二丙基酮、甲氧异丙烯、2,2-二甲氧丙烷、环戊酮、环己酮、1,1-二甲氧环戊烷、1,1-二甲氧环己烷等,优选丙酮、2,2-二甲氧丙烷、环戊酮、1,1-二甲氧环戊烷。
所使用的溶剂,只要是不抑制反应,可以一定程度溶解起始原料和反应试剂的都可以,对此没有特别的限制,但是优选使用与缩醛化试剂对应的式(Rp)2C=O所示化合物作为溶剂,优选丙酮或环戊酮。
所使用的酸催化剂,可列举例如,盐酸、硝酸、硫酸等无机酸;乙酸、三氟乙酸、甲磺酸、对甲苯磺酸等有机酸;三氟化硼等路易斯酸;或大孔树脂15(ァンバ一リスト15)等酸性树脂,优选有机酸或酸性树脂,更优选对甲苯磺酸或大孔树脂15(ァンバ一リスト15)。
反应温度根据所使用的缩醛化试剂和酸催化剂等变化,但是通常为0℃~100℃,优选20℃~50℃。
反应时间根据反应温度等变化,但是通常为1小时~7天,优选10小时~3天。
反应完成后,本反应的目的产物可按照常规方法从反应混合物中分离出来。例如,将反应混合物适当中和,或在存在不溶物时通过过滤除去不溶物后,减压蒸除溶剂,加入乙酸乙酯或二氯甲烷等与水不混溶的有机溶剂,用稀盐酸水溶液、碳酸氢钠水溶液、氯化钠水溶液等适当洗涤,用无水硫酸镁等干燥后,蒸除溶剂得到,如果需要,可通过常规方法,例如重结晶、再沉淀或色谱法进行纯化精制。
第B2工序是从化合物(B1)制备化合物(B2)的工序。该工序是通过将化合物(B1)在溶剂中与碱作用完成的。
所使用的碱可列举例如,氢氧化钠、氢氧化钾等碱金属氢氧化物,优选氢氧化钠。
所使用的溶剂,可列举例如,水;甲醇、乙醇、丙醇等醇类与水的混合溶剂;二噁烷、四氢呋喃等与水混溶的醚类与水的混合溶剂,优选醇类(特别是甲醇)与水的混合溶剂。
反应温度通常为-20℃~50℃,优选0℃~20℃。
反应时间根据反应温度等变化,通常为1分钟~1小时,优选5分钟~20分钟。
反应完成后,该反应的目的产物可用常规方法,例如,用离子交换树脂(ダゥエックス)50WX8等酸性树脂转化为游离羧酸衍生物,用常规方法从反应混合物中分离出来。例如,从反应液中过滤除去不溶物,将滤液减压浓缩,或者,加入乙酸乙酯或二氯甲烷等与水不混溶的有机溶剂,用稀盐酸水溶液、氯化钠水溶液等适当洗净,用无水硫酸镁等干燥后,蒸除溶剂得到,如果需要,可通过常规方法,例如重结晶、再沉淀或色谱法进行纯化。
第B3工序是从化合物(B2)制备化合物(B3)的工序。该工序是通过使化合物(B2)在惰性溶剂中在偶合试剂存在下与R1-X1H所示化合物反应完成的。
式R1-X1H所示化合物是具有所需R1和X1的醇类、硫醇类或胺类。
使用的偶合试剂,二环己基碳化二亚胺、二异丙基碳化二亚胺(DIPC)等碳化二亚胺类;苯磺酰氯、对甲苯磺酰氯等磺酰氯类;六氟磷酸苯并三唑-1-基氧三(二甲基氨基)鏻等鏻盐类;六氟磷酸O-苯并三唑-1-基-N,N,N’,N’-四甲基脲阳离子等脲阳离子盐类,但是优选碳化二亚胺类(特别是DIPC)。
作为偶合剂使用碳化二亚胺类时,可添加1-羟基苯并三唑(HOBT)。
作为使用的溶剂,只要不抑制反应,可以以一定程度溶解起始原料和反应剂的都可以,对此没有特别的限制,可列举例如,N,N-二甲基甲酰胺(DMF)、N,N-二甲基乙酰胺等酰胺类;二氯甲烷、氯仿等卤代烃;二噁烷、四氢呋喃等醚类,但优选酰胺类(特别是N,N-二甲基甲酰胺(DMF))。
反应温度通常为-20℃~80℃,优选0℃~50℃。
反应时间根据反应温度等变化,通常为1小时~2天,优选3小时~1天。
反应完成后,该反应的目的产物可用常规方法从反应混合物中分离出来。例如,通过适当中和反应混合物,或存在不溶物时通过过滤将其除去后,将滤液减压浓缩,加入乙酸乙酯或二氯甲烷等与水不混溶的有机溶剂,用稀盐酸水溶液、氯化钠水溶液等适当洗净,用无水硫酸镁等干燥后,蒸除溶剂得到,如果需要,可通过常规方法,例如重结晶、再沉淀或色谱法进行纯化。
第B4工序是从化合物(B3)制备化合物(Ib)的工序。该工序是通过将化合物(B3)在溶剂中与酸催化剂反应完成的。
使用的酸催化剂可列举例如,盐酸、硝酸、硫酸等无机酸;乙酸、三氟乙酸、甲磺酸、对甲苯磺酸等有机酸;三氟化硼等路易斯酸;或大孔树脂(ァンバ一リスト)15等酸性树脂,优选有机酸或酸性树脂,更优选三氟乙酸、对甲苯磺酸或大孔树脂(ァンバ一リスト)15。
所使用的溶剂,可列举例如,水;甲醇、乙醇等醇类,醇类与水的混合溶剂;二噁烷、四氢呋喃等与水混溶的醚类与水的混合溶剂;二氯甲烷、氯仿等卤代烃类;卤代烃与水的混合溶剂等,但优选醇类(特别是甲醇)或卤代烃类等(特别是二氯甲烷)。
反应温度通常为0℃~120℃,优选20℃~100℃。
反应时间根据反应温度等变化,通常为1小时~2天,优选3小时~1天。
反应完成后,该反应的目的产物可按照常规方法从反应混合物中分离出来。例如,将反应混合物适当中和,或在存在不溶物时通过过滤除去不溶物后,减压蒸除溶剂,加入乙酸乙酯或二氯甲烷等与水不混溶的有机溶剂,用稀盐酸水溶液、碳酸氢钠水溶液、氯化钠水溶液等适当洗涤,用无水硫酸镁等干燥后,蒸除溶剂得到,如果需要,可通过常规方法,例如重结晶、再沉淀或色谱法进行纯化。
另外,第B1工序的缩醛化反应和第B4工序的脱缩醛化反应是根据需要进行的工序,也可将化合物(VI)直接进行第B2工序的水解反应,制备式(VII)所示化合物,然后进行第B3工序的R1-X1基导入反应,制备目的化合物(Ib)。化合物(VII)可从后述的微生物产物中分离出来。
所得化合物(Ib),根据需要,可通过后述方法转化为R3是氢原子的化合物(Id)或醚或酯衍生物。
[C法]
C法是制备通式(I)中R3是羟基的化合物(Ic)的方法。
C法上式中,R1、R2、X1和X2定义同前,Rz表示酰基。
第C1工序是制备化合物(VI)的羟基被酰基保护的化合物(C1)的工序。该工序是通过将化合物(VI)在惰性溶剂中在碱存在下与酰化剂反应完成的。
所使用的溶剂,只要不抑制反应,可以以一定程度溶解起始原料和反应剂的都可以,对此没有特别的限制,可列举例如,乙醚、四氢呋喃、二噁烷等醚类;N,N-二甲基甲酰胺、N,N-二甲基乙酰胺等酰胺类;二氯甲烷、氯仿等卤代烃;乙腈;乙酸乙酯;吡啶、二甲基吡啶等,但优选N,N-二甲基甲酰胺和吡啶。
所使用的碱,可列举吡啶、二甲基吡啶、三甲基吡啶、4-N,N-二甲基氨基吡啶等,但优选吡啶和4-N,N-二甲基氨基吡啶。
所使用的酰化剂可列举例如,乙酰氯、丙酰氯、乙酸酐等碳原子数1~4的脂肪族酰卤化物或酸酐;苯甲酰氯、苯甲酰溴和苯甲酸酐等碳原子数6~10的芳族酰卤化物或酸酐,但优选苯甲酰氯或苯甲酸酐。
反应温度可根据使用的酰化剂和碱等变化,通常为-20℃~100℃,优选0℃~50℃。
反应时间根据反应温度等变化,通常为30分钟~1天,优选1小时~10小时。
反应完成后,该反应的目的产物可按照常规方法从反应混合物中分离出来。例如,通过将反应混合物适当中和,或在存在不溶物时通过过滤除去不溶物后,减压蒸除溶剂,加入乙酸乙酯或二氯甲烷等与水不混溶的有机溶剂,用稀盐酸水溶液、碳酸氢钠水溶液、氯化钠水溶液等适当洗涤,用无水硫酸镁等干燥后,蒸除溶剂而得到,如果需要,可通过常规方法,例如重结晶、再沉淀或色谱法进行纯化。
第C2工序是将化合物(D1)的氨基甲酰基水解制备化合物(C2)的工序。该工序是通过使化合物(D1)与亚硝基硫酸反应完成的。
所使用的溶剂,优选二氯甲烷和水的混合溶剂。
反应温度根据所使用的溶剂等变化,但是通常为-20℃~100℃,优选0℃~50℃。
反应时间根据反应温度等变化,但是通常为10分钟~5小时,优选20分钟~2小时。
反应完成后,该反应的目的产物可按照常规方法从反应混合物中分离出来。例如,通过将反应混合物适当中和,或在存在不溶物时通过过滤除去不溶物后,减压蒸除溶剂,加入乙酸乙酯或二氯甲烷等与水不混溶的有机溶剂,用稀盐酸水溶液、碳酸氢钠水溶液、氯化钠水溶液等适当洗涤,用无水硫酸镁等干燥后,蒸除溶剂而得到,如果需要,可通过常规方法,例如重结晶、再沉淀或色谱法进行纯化。
第C3工序是向化合物(C2)中导入R2-X2基制备化合物(C3)的工序。该工序可将化合物(C2)作为原料使用,按照第B3工序进行。
第C4工序是将化合物(C3)碱水解制备化合物(C4)的工序。该工序可将化合物(C3)作为原料使用,按照第B2工序进行。
第C5工序是向化合物(C4)中导入R1-X1基制备化合物(Ic)的工序。该工序可将化合物(C4)作为原料使用,按照第B3工序进行。
所得化合物(Ic),可根据需要,通过后述方法,转化为R3是氢原子的化合物(Id)或醚或酯衍生物。
[D法]
D法是制备通式(I)中R3是氢原子的化合物(Id)的方法。
D法
上式中,R1、R2、X1、X2和Rp定义同前。
第D1工序是将化合物(Ic)的羟基用缩醛化试剂保护制备化合物(D1)的工序。该工序可使用化合物(Ic)作为原料,按照第B1工序进行。
第D2工序是向化合物(D1)中导入苯氧硫代羰基制备化合物(D2)的工序。该工序是通过使化合物(D1)在惰性溶剂中在碱存在下与苯氧硫代羰基化试剂反应完成的。
作为使用的苯氧硫代羰基化试剂,可列举例如,苯氧硫代羰基卤化物或苯氧羰基羧酸酐,优选苯氧硫代羰基氯。
所使用的溶剂,只要不抑制反应,可以以一定程度溶解起始原料和反应剂的都可以,对此没有特别的限制,可列举例如,二氯甲烷、氯仿等卤代烃;乙醚、四氢呋喃、二噁烷等醚类;苯、甲苯等芳族烃类;吡啶等,优选卤代烃类。
所使用的碱,可列举吡啶、二甲基吡啶、三甲基吡啶、三乙胺、4-N,N-二甲基氨基吡啶等,但优选4-N,N-二甲基氨基吡啶。
反应温度根据所使用溶剂和碱等变化,但是通常为-20℃~100℃,优选0℃~50℃。
反应时间根据反应温度等变化,但是通常为30分钟~10小时,优选1小时~3小时。
反应完成后,该反应的目的产物可按照常规方法从反应混合物中分离出来。例如,通过将反应混合物适当中和,或在存在不溶物时通过过滤除去不溶物后,减压蒸除溶剂,加入乙酸乙酯或二氯甲烷等与水不混溶的有机溶剂,用稀盐酸水溶液、碳酸氢钠水溶液、氯化钠水溶液等适当洗涤,用无水硫酸镁等干燥后,蒸除溶剂而得到,如果需要,可通过常规方法,例如重结晶、再沉淀或色谱法进行纯化。
第D3工序是将化合物(D2)的苯氧硫代羰基氧基还原除去制备化合物(D3)的工序。该工序是通过使化合物(D3)在惰性溶剂中,在自由基反应引发剂存在下,与氢化锡类反应完成的。
作为使用的氢化锡类,可列举例如,三丁基氢化锡和三苯基氢化锡,优选三丁基氢化锡。
所使用的溶剂,可列举例如,二氯甲烷、氯仿等卤代烃;乙醚、四氢呋喃、二噁烷等醚类;苯、甲苯等芳族烃类,优选甲苯。
所使用的自由基反应引发剂,优选2,2’-偶氮双异丁腈(AIBN)。
反应温度根据所使用的溶剂和碱等变化,但是通常为20℃~150℃,优选80℃~120℃。
反应时间根据反应温度等变化,但是通常为1小时~3天,优选5小时~1天。
反应完成后,该反应的目的产物可按照常规方法从反应混合物中分离出来。例如,通过将反应混合物适当中和,或在存在不溶物时通过过滤除去不溶物后,减压蒸除溶剂,加入乙酸乙酯或二氯甲烷等与水不混溶的有机溶剂,用稀盐酸水溶液、碳酸氢钠水溶液、氯化钠水溶液等适当洗涤,用无水硫酸镁等干燥后,蒸除溶剂而得到,如果需要,可通过常规方法,例如重结晶、再沉淀或色谱法进行纯化。
第D4工序是除去化合物(D3)的羟基的缩醛保护基制备化合物(Id)的工序。该工序可将化合物(D3)作为原料,按照第B4工序进行。
所得化合物(Id),可根据需要,通过后述方法,转化为醚或酯衍生物。
[E法]
E法是制备通式(I)所示化合物的醚衍生物(E4)的方法。
E法
Figure A0081465303001
上式中,R1、R2、X1、X2和Rp定义同前,R8表示前述醚残基,Ru表示尿嘧啶残基的保护基。
第E1工序是向化合物(D1)的尿嘧啶残基中导入保护基制备化合物(E1)的工序。该工序是通过使化合物(D1)在惰性溶剂中,在碱存在下,与尿嘧啶残基的保护化试剂反应完成的。
作为尿嘧啶残基的保护化试剂,优选对甲氧苄基氯甲基醚。
所使用的溶剂,只要不抑制反应,可以以一定程度溶解起始原料和反应剂的都可以,对此没有特别的限制,可列举例如,乙醚、四氢呋喃、二噁烷等醚类;N,N-二甲基甲酰胺、N,N-二甲基乙酰胺等酰胺类;二氯甲烷、氯仿等卤代烃;乙腈,但优选N,N-二甲基甲酰胺和乙腈。
所使用的碱,例如是1,8-二杂氮双环[5.4.0]十一碳烯-7-烯(DBU)、1,5-二杂氮双环[4.3.0]壬-5-烯(DBN)等叔胺类,或氢化钠、氢化钾等碱金属氢化物,优选1,8-二杂氮双环[5.4.0]十一碳烯-7-烯(DBU)。
反应温度根据所使用的缩醛化试剂和酸催化剂等变化,但是通常为0℃~100℃,优选20℃~50℃。
反应时间根据反应温度等变化,但是通常为30分钟~1天,优选1小时~5小时。
反应完成后,该反应的目的产物可按照常规方法从反应混合物中分离出来。例如,通过将反应混合物适当中和,或在存在不溶物时通过过滤除去不溶物后,减压蒸除溶剂,加入乙酸乙酯或二氯甲烷等与水不混溶的有机溶剂,用稀盐酸水溶液、碳酸氢钠水溶液、氯化钠水溶液等适当洗涤,用无水硫酸镁等干燥后,蒸除溶剂得到,如果需要,可通过常规方法,例如重结晶、再沉淀或色谱法进行纯化。
第E2工序是向化合物(E1)的羟基中导入醚残基制备化合物(E2)的工序。该工序可通过使化合物(E1)在惰性溶剂中,碱存在下,使具有通式(C1)的化合物与醚化试剂反应完成的。
所使用的醚化试剂是式R8L所示的化合物(R8是前述醚残基,L是离去基团),例如可列举R8的卤化物、三氟甲磺酸酯化物等,优选碘化物。
所使用的溶剂,可列举例如,乙醚、四氢呋喃、二噁烷等醚类;N,N-二甲基甲酰胺、N,N-二甲基乙酰胺等酰胺类;二氯甲烷、氯仿等卤代烃;乙腈,优选N,N-二甲基甲酰胺。
所使用的碱,例如是1,8-二杂氮双环[5.4.0]十一碳烯-7-烯(DBU)、1,5-二杂氮双环[4.3.0]壬-5-烯(DBN)等叔胺类,或氢化钠、氢化钾等碱金属氢化物,优选碱金属氢化物。
反应温度根据所使用的缩醛化试剂和酸催化剂等变化,但是通常为-30℃~100℃,优选-10℃~30℃。
反应时间根据反应温度等变化,但是通常为30分钟~1天,优选1小时~5小时。
反应完成后,该反应的目的产物可按照常规方法从反应混合物中分离出来。例如,通过将反应混合物适当中和,或在存在不溶物时通过过滤除去不溶物后,减压蒸除溶剂,加入乙酸乙酯或二氯甲烷等与水不混溶的有机溶剂,用稀盐酸水溶液、碳酸氢钠水溶液、氯化钠水溶液等适当洗涤,用无水硫酸镁等干燥后,蒸除溶剂得到,如果需要,可通过常规方法,例如重结晶、再沉淀或色谱法进行纯化。
第E3工序,是除去化合物(E2)的尿嘧啶残基的保护基制备化合物(E3)的工序。该工序是使化合物(E2)在惰性溶剂中,与脱保护试剂反应完成的。
作为使用的脱保护试剂,可列举例如,2,3-二氯-5,6-二氰基-1,4-苯醌(DDQ)或硝酸铈(IV)铵(CAN),但优选2,3-二氯-5,6-二氰基-1,4-苯醌(DDQ)。
所使用的溶剂,只要不抑制反应,可以以一定程度溶解起始原料和反应剂的都可以,对此没有特别的限制,可列举例如,水;甲醇、乙醇等醇类;乙醚、四氢呋喃、二噁烷等醚类;二氯甲烷、氯仿等卤代烃以及它们的混合溶剂,但优选二氯甲烷和水的混合溶剂。
反应温度根据所使用的缩醛化试剂和酸催化剂等变化,但是通常为0℃~150℃,优选10℃~100℃。
反应时间根据反应温度等变化,但是通常为1小时~2天,优选1小时~10小时。
反应完成后,该反应的目的产物可按照常规方法从反应混合物中分离出来。例如,通过将反应混合物适当中和,或在存在不溶物时通过过滤除去不溶物后,减压蒸除溶剂,加入乙酸乙酯或二氯甲烷等与水不混溶的有机溶剂,用稀盐酸水溶液、碳酸氢钠水溶液、氯化钠水溶液等适当洗涤,用无水硫酸镁等干燥后,蒸除溶剂得到,如果需要,可通过常规方法,例如重结晶、再沉淀或色谱法进行纯化。
第E4工序是除去化合物(E3)的羟基的保护基制备化合物(E4)的工序。该工序可使用化合物(E3)作为原料,按照第B4工序进行。
使用该方法,可得到化合物(I)的氧杂环戊烷(ォキソラン)环只有3位羟基具有醚残基的醚衍生物(E4)。
所得化合物(E4),可根据需要,通过后述方法转化为酯衍生物。即,通过使醚衍生物(E4)与酯化剂反应,可制备在氧杂环戊(オキソラン)环3位的羟基中具有醚残基,在二氢吡喃环的羟基中导入酯残基的衍生物。
[F法]
F法是制备通式(I)所示化合物的酯衍生物(F2)的方法。
F法
上式中,R1、R2、X1、X2和Rp定义同前,R9是前述酯残基。
第F1工序是向化合物(D1)的羟基中导入酯残基制备化合物(F1)的工序。该工序是通过使化合物(D1)在惰性溶剂中,碱存在下,与具有所需酯残基的酰卤化物或酸酐反应完成的。
所使用的酰卤化物或酸酐,例如,式RaCO-Y、RaCO2CO2R10、RaCO-O-CORa或RaOCO-Y表示的化合物[式中,Ra定义同前、Y表示卤原子、(优选是氯或溴原子)、R10表示碳原子数1~4的烷基(优选乙基或异丙基)]、甲酸和乙酸的混合酸酐、琥珀酸酐、戊二酸酐、己二酸酐等环状酸酐,或者作为磷酸酯化剂,式(R11aO)(R11bO)PO-Y表示的化合物[式中,Y定义同前,R11a和R11b可相同或不同,表示碳原子数2~16的烷基),优选式RaCO-Y、RaCO2CO2R10、RaCO-O-CORa或RaOCO-Y表示的化合物(式中,Ra、Y、R10定义同上)。
所使用的碱,例如是氢氧化锂、氢氧化钠、氢氧化钾等碱金属氢氧化物;碳酸锂、碳酸钠、碳酸钾等碱金属碳酸盐;碳酸氢钠、碳酸氢钾等碱金属碳酸氢盐;甲醇锂、甲醇钠、乙醇钠、丁醇锂等碱金属醇化物;三乙胺、三丁胺、N-甲基吗啉、吡啶、4-二甲基氨基吡啶、甲基吡啶、二甲基吡啶、三甲基吡啶、1,5-二氮杂双环[4.3.0]壬-5-壬烯、1,8-二氮杂双环[5.4.0]十一碳-7-烯等有机胺类,优选有机胺类,特别优选三乙胺、三丁胺、吡啶或二甲基吡啶。另外,在使用液体有机胺类时,也可兼作溶剂而大量过量使用。
在前述的酯化反应中,对于磷酸酯化,也可通过在不溶性溶剂中,在酸或碱的存在下,使化合物(D1)与具有所希望的酯残基的亚磷酸盐反应后,使用氧化剂氧化成磷酸酯而进行的。
所使用的亚磷酸盐,例如是式(R11aO)(R11bO)P-Z表示的化合物[式中,R11a表示碳原子数2~16的烷基,R11b表示碳原子数2~16的烷基或2-氰基乙基,Z表示卤素或式-N(iPr)2所示基团]。
上述式中,Z是卤素时,作为反应助剂可使用碱,但使用的碱与前述的意义相同。另外,上述式中的Z不是卤素时,作为反应助剂可使用酸。所使用的酸,只要是显示醋酸程度的酸性度的酸就可以使用,但优选的是四唑。
作为使用的氧化剂,可列举例如间氯过苯甲酸、叔丁基氢过氧化物、过乙酸等,但优选间氯乙酸。
所使用的惰性溶剂,只要与反应无关,没有特别限制,例如是己烷、苯、甲苯等烃类;二氯甲烷、氯仿、四氯化碳、1,2-二氯乙烷等卤代烃类;乙醚、四氢呋喃、二噁烷等醚类;丙酮、甲基乙基酮等酮类;乙腈等腈类;N,N-二甲基甲酰胺、N,N-二甲基乙酰胺、N-甲基-2-吡咯烷酮、六甲基磷酰胺等酰胺类;二甲基亚砜等亚砜类或它们的混合溶剂,优选烃类或酰胺类。
反应温度根据原料化合物(D1)、酰卤化物等和溶剂的种类而不同,但通常是-10℃~100℃(优选的是0℃~50℃)、反应时间根据反应温度而不同,是10分钟~2天(优选30分钟~10小时)。
当使用R11b是2-氰基乙基的上述亚磷酸酯时,在氧化反应终止后,所得到的烷基(2-氰基乙基)磷酸酯用含有例如氨水等的碱的水处理,2-氰基乙基水解,能得到对应的单-烷基磷酸酯衍生物。
另外,酯化反应还可通过在惰性溶剂中,在缩合剂存在下,使化合物(D1)与具有所需酯残基的羧酸反应完成。
使用的缩合剂,例如为,二环己基碳化二亚胺等碳化二亚胺类,羰基二咪唑或1-(N,N-二甲基氨基丙基)-3-甲基碳二亚胺盐酸盐,优选二环己基碳化二亚胺类。
所使用的惰性溶剂,只要与反应无关,没有特别限制,例如是己烷、苯、甲苯等烃类;二氯甲烷、氯仿、四氯化碳、1,2-二氯乙烷等卤代烃类;乙醚、四氢呋喃、二噁烷等醚类;丙酮、甲基乙基酮等酮类;乙腈等腈类;N,N-二甲基甲酰胺、N,N-二甲基乙酰胺、N-甲基-2-吡咯烷酮、六甲基磷酰胺等酰胺类;二甲基亚砜等亚砜类或它们的混合溶剂,优选烃类、卤代烃类或酰胺类。
反应温度根据原料化合物(D1)、羧酸等和溶剂的种类而不同,但通常是-10℃~100℃(优选的是0℃~50℃)、反应时间根据反应温度而不同,是10分钟~2天(优选30分钟~10小时)。
反应完成后,各反应的目的产物可按照常规方法从反应混合物中分离出来。例如,通过将反应混合物适当中和,或在存在不溶物时通过过滤除去不溶物后,减压蒸除溶剂,加入乙酸乙酯或二氯甲烷等与水不混溶的有机溶剂,用稀盐酸水溶液、碳酸氢钠水溶液、氯化钠水溶液等适当洗涤,用无水硫酸镁等干燥后,蒸除溶剂得到,如果需要,可通过常规方法,例如重结晶、再沉淀或色谱法进行纯化。
第F2工序是除去化合物(F1)的羟基的保护基制备化合物(F2)的工序。该工序可使用化合物(F1)作为原料,按照第B4工序进行。
通过该方法,可得到化合物(I)的氧杂环戊烷环只有3位羟基中具有酯残基的衍生物(F2)。
另外,通过使酯衍生物(F2)与1当量的酯化试剂反应,可制备除了在氧杂环戊烷环的3位之外,在二氢吡喃环的羟基中导入一个酯残基的酯衍生物。另外,通过再与1当量的酯化试剂反应,可制备全部羟基中导入了酯残基的酯衍生物。这些酯残基可相同或不同。
另一方面,通过向酯衍生物(F2)的尿嘧啶残基中导入保护基,与醚化试剂作用,接着除去尿嘧啶残基的保护基,可制备在氧杂环戊烷环3位羟基中有酯残基,二氢吡喃环的羟基中导入了醚残基的衍生物。
另外,使用1~3摩尔的酯化试剂将式(I)所示化合物进行酯化,可得到1~3个羟基被酯化的化合物的混合物。将其用柱色谱分离纯化,可制备化合物(I)的只有1个羟基被酯化的衍生物,2个羟基被酯化的衍生物和3个羟基被酯化的衍生物。另外,对于只有1个羟基被酯化的衍生物和2个羟基被酯化的衍生物,通过与1~2当量的酯化试剂反应,可制备2个或3个羟基被酯化的酯衍生物。这些酯残基可相同或不同。
另外,通过向只有1个羟基被酯化的衍生物和2个羟基被酯化的衍生物的尿嘧啶残基导入保护基,与醚化试剂作用,接着除去尿嘧啶残基的保护基,可制备具有酯残基和醚残基的衍生物。
[G法]
G法是制备通式(I)中X2是-NH-所示基团,R3是羟基的化合物(G3)的方法。
G法
上式中,R1、R2、X1和Rz定义同前。
第G1工序是向用前述B法得到的化合物(Ib)的羟基中导入保护基Rz制备化合物(G1)的工序。该工序可将化合物(Ib)作为起始原料,按照前述第C1工序同样进行。
第G2工序是将化合物(G1)的氨基甲酰基水解转化为羧基后,进一步甲基化,得到化合物(G2)的工序。该工序的水解可按照前述第C2工序同样完成。甲基化工序是通过将所得羧酸化合物在溶剂中与重氮甲烷作用完成的。
甲基化工序中使用的溶剂,可列举例如,二氯甲烷,乙醚,四氢呋喃,以及它们的混合溶剂,优选二氯甲烷和乙醚的混合溶剂。
反应温度根据所使用溶剂等变化,但是通常为-20℃~100℃,优选0℃~50℃。
反应时间根据反应温度等变化,但是通常为5分钟~2小时,优选10分钟~30分钟。
反应完成后,该反应的目的产物可按照常规方法从反应混合物中分离出来。例如,通过将反应混合物适当中和,或在存在不溶物时通过过滤除去不溶物后,减压蒸除溶剂,加入乙酸乙酯或二氯甲烷等与水不混溶的有机溶剂,用稀盐酸水溶液、碳酸氢钠水溶液、氯化钠水溶液等适当洗涤,用无水硫酸镁等干燥后,蒸除溶剂得到,如果需要,可通过常规方法,例如重结晶、再沉淀或色谱法进行纯化。
G3工序是将化合物(G2)的酯部分转化为酰胺制备化合物(G3)的工序。该工序是通过使化合物(G2)在溶剂中与具有所需取代基R2的胺作用完成的。
使用的溶剂,可列举例如甲醇、乙醇等醇类,优选甲醇。
反应温度根据所使用的胺或溶剂等变化,但是通常为0℃~100℃,优选20℃~50℃。
反应时间根据反应温度等变化,但是通常为1小时~5天,优选10小时~2天。
反应完成后,该反应的目的产物可按照常规方法从反应混合物中分离出来。例如,通过将反应混合物适当中和,或在存在不溶物时通过过滤除去不溶物后,减压蒸除溶剂,加入乙酸乙酯或二氯甲烷等与水不混溶的有机溶剂,用稀盐酸水溶液、碳酸氢钠水溶液、氯化钠水溶液等适当洗涤,用无水硫酸镁等干燥后,蒸除溶剂而得到,如果需要,可通过常规方法,例如重结晶、再沉淀或色谱法进行纯化。
[H法]
H法是制备通式(I)化合物的N-烷基衍生物(H4)的方法。
H法
上式中,R1、Rp和X1定义同前。Rs表示羟基的保护基(甲硅烷基系保护基),优选三甲基甲硅烷基,三乙基甲硅烷基,叔丁基二甲基甲硅烷基等三烷基甲硅烷基,特别优选叔丁基二甲基甲硅烷基。R12表示碳原子数1~21的直链或支链烷基,碳原子数2~21的直链或支链不饱和烷基,1-(碳原子数2~20的烷酰氧基)碳原子数1~3的烷基或1-(碳原子数1~20的烷氧羰基氧基)碳原子数1~3的烷基。
第H1工序是向化合物(B3)的羟基导入保护基Rs制备化合物(H2)的工序。该工序是,在惰性溶剂中,使化合物(H2)在惰性溶剂中,碱存在下,与羟基的保护化试剂作用制备化合物(H1)的工序。
作为使用的羟基的保护化试剂,可列举例如,三甲基甲硅烷基氯,叔丁基二甲基甲硅烷基氯等三烷基甲硅烷基卤化物或叔丁基二甲基甲硅烷基三氟甲磺酸酯等三烷基甲硅烷基三氟甲磺酸酯,优选叔丁基二甲基甲硅烷基氯。
使用的溶剂可列举例如,二氯甲烷、氯仿等卤代烃类;二甲基甲酰胺、二甲基乙酰胺、吡啶等,优选咪唑或吡啶。
使用的碱可列举例如,咪唑,吡啶或4-二甲基氨基吡啶等,优选咪唑或吡啶。
反应温度根据所使用的溶剂等变化,但是通常为-20℃~100℃,优选0℃~50℃。
反应时间根据反应温度等变化,但是通常为30分钟~1天,优选1小时~5小时。
反应完成后,该反应的目的产物可按照常规方法从反应混合物中分离出来。例如,通过将反应混合物适当中和,或在存在不溶物时通过过滤除去不溶物后,减压蒸除溶剂,加入乙酸乙酯或二氯甲烷等与水不混溶的有机溶剂,用稀盐酸水溶液、碳酸氢钠水溶液、氯化钠水溶液等适当洗涤,用无水硫酸镁等干燥后,蒸除溶剂得到,如果需要,可通过常规方法,例如重结晶、再沉淀或色谱法进行纯化。
第H2工序是向化合物(H1)的尿嘧啶残基的3位氮原子中导入所需烷基(R12),制备化合物(H3)的工序。该工序是通过使化合物(H1)在惰性溶剂中,碱存在下,与N-烷基化试剂作用完成的。
作为使用的N-烷基化试剂,优选烷基氯、烷基溴、烷基碘等烷基卤化物。
所使用的碱,可列举例如,碳酸钠、碳酸钾等碱金属碳酸盐;碳酸氢钠;氢化钠、氢化锂等碱金属氢化物;1,8-二氮杂双环[5.4.0]十一碳烯-7-烯(DBU)、1,5-二氮杂双环[4.3.0]壬-5-烯(DBN)等叔胺类,但优选碳酸钾或DBU。
使用的溶剂,可列举例如,二氯甲烷、氯仿等卤代烃类;二甲基甲酰胺、二甲基乙酰胺、吡啶等,优选二甲基甲酰胺。
反应温度根据所使用的溶剂等变化,但是通常为-20℃~120℃,优选20℃~80℃。
反应时间根据反应温度等变化,但是通常为1小时~1天,优选3小时~10小时。
反应完成后,该反应的目的产物可按照常规方法从反应混合物中分离出来。例如,通过将反应混合物适当中和,或在存在不溶物时通过过滤除去不溶物后,减压蒸除溶剂,加入乙酸乙酯或二氯甲烷等与水不混溶的有机溶剂,用稀盐酸水溶液、碳酸氢钠水溶液、氯化钠水溶液等适当洗涤,用无水硫酸镁等干燥后,蒸除溶剂得到,如果需要,可通过常规方法,例如重结晶、再沉淀或色谱法进行纯化。
第H3工序是除去化合物(H2)的羟基的保护基Rs制备化合物(H3)的工序。该工序是通过使化合物(H2)在惰性溶剂中与Rs的脱保护试剂作用完成的。
作为使用的Rs的脱保护试剂,可列举例如,四丁基氟化铵或氟化铯等,但优选四丁基氟化铵。
使用的溶剂可列举例如,四氢呋喃、乙醚、乙腈等,优选四氢呋喃。
反应温度根据所使用的溶剂等变化,但是通常为-20℃~100℃,优选0℃~50℃。
反应时间根据反应温度等变化,但是通常为30分钟~10小时,优选1小时~3小时。
反应完成后,该反应的目的产物可按照常规方法从反应混合物中分离出来。例如,通过将反应混合物适当中和,或在存在不溶物时通过过滤除去不溶物后,减压蒸除溶剂,加入乙酸乙酯或二氯甲烷等与水不混溶的有机溶剂,用稀盐酸水溶液、碳酸氢钠水溶液、氯化钠水溶液等适当洗涤,用无水硫酸镁等干燥后,蒸除溶剂得到,如果需要,可通过常规方法,例如重结晶、再沉淀或色谱法进行纯化。
第H4工序是除去化合物(H3)的羟基的保护基制备化合物(H4)的工序。该工序可使用化合物(H3)作为原料,按照第B4工序进行。
另一方面,作为A法至C法起始原料使用的化合物(VI)和化合物(VII),可按照WO00/02892号记载的方法制备。即,是通过在适当的培养基中培养属于链霉菌属(Streptomyces spp.)的该化合物的生产菌,从该培养物收集得到。可通过常法从茨城县筑波山的土壤采集、分离得到作为化合物(VI)和(VII)的合适生产菌的灰色链霉菌(Streptomyces griseus)SANK60196株(以下称“SANK60196株”)。SANK 60196株的细菌学的性状,如下所示。
1)形态学的特征
SANK60196株在国际·链霉菌·工程(InternationalStreptomyces Project;以下称“ISP”)规定[参照西林格及戈特杂志系统微生物:Shirling,E.B.and Gottlieb,D.(1966)Int.J.Syst.Bacteriol.16,313-340]的培养基上在28℃下培养14天显示如下形态学的特征。在用光学显微镜观察时,SANK 60196的基内菌丝生长、分支良好,显示黄灰、黄褐乃至淡橄榄色,但未观察到诺卡氏菌属(Nocardia)菌株样的断裂或锯齿伸长。气生菌丝体简单分支。孢子链的状态显示是直的或弯曲状,形成约10至50个或以上的孢子的链。用扫描型电子显微镜观察,孢子是椭圆形的,其表面结构显示平滑状(Smooth)。孢子的大小是0.6~0.8×0.7~1.2mm。只是在气生菌丝体上形成孢子。另外,没有看到孢子囊、气生菌丝体的轴向分支、气生菌丝的断裂、菌核等特殊器官形成。
2)在各种培养基上的培养性质
SANK60196株在28℃下培养14天后,在琼脂培养基上的培养性状,如表4所示。表中,记有ISP号的培养基的组成分别如ISP的规定所示。另外,项目G表示生长、AM表示气生菌丝体、R表示反面、SP表示可溶性色素。色调的描述是用“颜色标准(日本色彩研究所版)”进行的,括弧内的色调的表示是根据孟塞尔色体系的色号。水琼脂培养基中产生的浅黄色的可溶性色素,用0.05N盐酸变成无色,但通过0.05N氢氧化钠未显示出任何变化。
表4
培养基的种类;
项目:性状酵母提取物·麦芽提取物琼脂(I SP 2);
      G:非常良好、平坦、黄褐色(10YR 5/6)
     AM:丰富地形成、天鹅绒状、浅褐色(2.5Y 8/2)
      R:黄褐色(10YR 5/8)
     SP:黄褐色(10YR 6/8)燕麦片琼脂(ISP 3);
      G:非常良好、平坦、黄褐色(2.5Y 6/6)
     AM:丰富地形成、天鹅绒状、浅黄褐橙色(5Y 9/2)
      R:暗黄(2.5Y 8/8)
     SP:未产生淀粉·无机盐琼脂(ISP 4);
      G:良好、平坦、黄褐色(2.5Y 6/4)
     AM:丰富地形成、天鹅绒状、黄灰色(7.5Y 9/2)
      R:黄褐色(2.5Y 6/4)甘油·天冬酰胺琼脂(ISP 5);
      G:非常良好、平坦、浅黄褐色(2.5Y 7/6)
     AM:丰富地形成、天鹅绒状、黄灰色(5Y 8/2)
      R:浅黄褐色(2.5Y 8/6)
     SP:未产生胨·酵母提取物·铁琼脂(ISP 6);
      G:非常良好、平坦、浅橄榄色(5Y 8/3)
     AM:稍微地形成、天鹅绒状、黄灰色(5Y 9/1)
      R:浅黄(5Y 8/6)
     SP:未产生酪氨酸琼脂(ISP 7);
      G:良好、平坦、灰黄褐色(2.5Y 5/4)
     AM:丰富地形成、天鹅绒状、亮橄榄灰(7.5Y 8/2)
      R:黄褐色(10YR 5/4)
     SP:灰黄褐色(2.5Y 4/3)蔗糖·硝酸盐琼脂;
      G:不太好、平坦、浅黄(5Y 8/6)
     AM:丰富地形成、天鹅绒状、亮橄榄灰(7.5Y 8/2)
      R:暗黄(5Y 8/8)
     SP:浅黄(5Y 9/6)葡萄糖·天冬酰胺琼脂;
      G:良好、平坦、浅黄(5Y 9/3)
     AM:不太好、天鹅绒状、黄灰色(5Y 9/1)
      R:黄灰色(7.5Y 9/3)
     SP:未产生营养琼脂(Difco社制);
      G:良好、平坦、浅黄褐色(2.5Y 8/3)
     AM:良好、天鹅绒状、黄灰色(5Y 9/1)
      R:黄灰色(5Y 9/4)
     SP:未产生马铃薯提取物·胡萝卜提取物琼脂;
      G:不太好、平坦、黄灰色(7.5Y 9/2)
     AM:不太好、天鹅绒状、黄灰色(5Y 9/2)
      R:黄灰色(7.5Y 9/3)
     SP:黄灰色(7.5Y 9/3)水琼脂;
      G:不太好、平坦、黄灰色(5Y 9/1)
     AM:不太好、天鹅绒状、黄灰色(5ZY 9/1)
      R:黄灰色(7.5Y 9/4)
     SP:浅黄(5Y 9/6)3)生理学的性质
在28℃培养后,观察2~21天的本菌株的生理学性质,如表5所示,表中培养基1表示酵母提取物·麦芽提取物琼脂(ISP 2)。
表5淀粉的水解                                              阳性明胶的液化                                              阳性硝酸盐的还原性                                          阳性牛奶的凝固                                              阴性牛奶的胨化                                              阳性黑色素样色素生产性                                      阳性基质分解性:酪蛋白                                      阳性
        酪氨酸                                      阳性
        黄嘌呤                                      阴性生长温度范围(培养基1)                                   6~35℃生长适宜温度(培养基1)                                   18~30℃在食盐存在下的生长(培养基)10%
另外,使用プリドハム·ゴトリ一ブ(Pridham-Gottlieb)琼脂培养基(ISP 9),在28℃下培养14天后观察到的SANK60196株的碳源的同化性,如表6所示。表中,“+”表示可同化的、“-”表示不可同化的。
表6D-葡萄糖                                                +L-阿拉伯糖                                              -D-木糖                                                  +肌醇                                                    -D-甘露醇                                                +D-果糖                                                  +L-鼠李糖                                                -蔗糖                                                    -蜜三糖                                                  -对照                                                    -
4)化学分类学的性质
按照长谷川等的方法[参照微生物应用杂志:Hasegawa、T.,等人、(1983)The Journal of General and Applied Microbiology 29、319-322]研究本菌株的细胞壁的结果,检测出LL-二氨基庚二酸。另外,按照M.P.来其沃勒的方法[参照M.P.来其沃勒:Lechevalier、M.P.,(1968)Journal of Laboratory and Clinical Medicine 71、934-944]研究本菌株的全细胞中的主要糖成分的结果,未检测出特征的成分。
从以上的菌学性质表明,本菌株属于放线菌菌中的链霉菌属(Streptomyces)。在与谢林格和戈特里布的ISP菌株记载[参照Shirling,E.B.and Gottlieb,D.,International Journal ofSystematic Bacteriology 18,68-189和279-392(1968);19,391-512(1969);22,265-394(1972)]、瓦克斯曼著的、二·放线菌属第2卷(参照Waksman、S.A.(1961)The Actinomyectes 2)、布卡能和戈蓬编的细菌鉴定手册(参照R.E.Buchanan and N.E.Gibbons;Bergey′s Manual of Determinative Bacteriology)第8版(1974年)、维利阿母斯等编的细菌分类Bergey’s手册[参照Williams,S.T.等人.(1989)Bergey′s Manual of SystematicBacteriology 4]以及关于链霉菌属(Streptomyces)放线菌的最近的文献记载的菌种比较时,表明与灰色链霉菌(Streptomycesgriseus)是极近缘的。但是,所说的灰色链霉菌(Streptomycesgriseus)是在甘油·天冬酰胺琼脂中产生黄灰色的可溶性色素、在胨·酵母提取物·铁琼脂中产生浅黄褐色的可溶性色素,但在马铃薯提取物·胡萝卜提取物琼脂及水琼脂中不产生可溶性色素、生长上限温度是40℃,及在存在食盐7%下的生长中看到了差异。
可明确地认为具有这样的菌学特征的本菌株是与灰色链霉菌(Streptomyces griseus)不同的新菌种,但仅具有这些差异,还不能区别种类。因此,本发明者等将本菌株鉴定为灰色链霉菌(Streptomyces griseus)SANK’60196。
该菌株于平成8年(1996年)2月22日在通商产业省工业技术院生命工学工业技术研究所(日本茨城县筑波市东1丁目1番3号邮政编码305-0046),以其为FERM BP-5420、进行了国际保藏。
以上,对于SANK60196进行了说明,但众所周知,放线菌的各性质不是一定的,容易自然地、人工地变化。在本发明使用的菌株包含其所有的变异株。即在本发明使用的菌株,包含属于链霉菌属、生产化合物(VI)或(VII)的所有菌株。
作为培养化合物(VI)或(VII)生产菌时使用的培养基,只要是适当含有从碳源、氮源、无机离子和有机营养源等选择的物质的培养基就可以,可使用任何合成或天然培养基。
作为该营养源,可使用以往真菌类或放线菌类菌株培养中所利用的公知的、微生物可同化的碳源、氮源和无机盐。
具体地说,作为碳源,可单一或并用葡萄糖、果糖、麦芽糖、蔗糖、甘露糖、甘油、糊精、燕麦、黑麦、玉米淀粉、土豆、玉米粉、大豆粉、棉籽油、糖稀、糖蜜、大豆油、柠檬酸、酒石酸等。一般在培养基量的1~10重量%变量,但不限于此范围。
另外,作为氮源,一般可使用含有蛋白质或其水解物的物质。作为适宜的氮源,例如可使用大豆粉、麸子、花生粉、棉籽粉、脱脂乳、酪蛋白水解物、ファ一マミン(Shefield Chemical社制)、鱼粉、玉米淀粉、胨、肉提取物、生酵母、干酵母、酵母提取物、麦芽提取物、土豆、硫酸铵、硝酸铵、硝酸钠等。该氮源,可单一或并用,优选在培养基量的0.2~6重量%的范围使用。
作为营养无机盐,可使用可得到钠、铵、钙、磷酸盐、硫酸盐、氯化物、碳酸盐等的离子的通常盐类。另外,也可使用钾、钙、钴、锰、铁、镁等的微量金属。
在化合物(VI)或(VII)的生产中添加钴、脱脂乳和酵母提取物是有效的。
另外,在培养该生产菌时,添加抗生物质生物合成抑制剂,也可生产化合物(VI)或(VII)。化合物(VI)或(VII)的生产,例如,可通过将作为天冬氨酸激酶抑制剂的S-(2-氨基乙基)-L-半胱氨酸或其盐作为培养基添加剂单独使用或与钴、脱脂乳和酵母提取物并用完成。该添加剂,特别是通过与脱脂乳并用,可提高化合物(VI)和(VII)的生产性。该添加剂,作为最终浓度可在1~100mM的范围使用。优选作为最终浓度以10mM可生产优良的化合物(VI)和(VII)。
另外,在液体培养时,作为消泡剂可使用硅油、植物油、表面活性剂等。
为培养SANK60196株生产化合物(VI)和(VII)的培养基的pH,优选的是5.0~8.0。
SANK60196株的生长温度是12~36℃,但为了生产化合物(VI)和(VII),优选在18~28℃下培养该菌株,更优选在19~23℃下培养。
化合物(VI)和(VII)可通过需氧培养SANK60196株得到,作为这样的培养方法,可使用通常使用的需氧的培养法,例如固体培养法、振荡培养法、通气搅拌培养法等。
在小规模的培养中,优选在19~23℃下振荡培养几天。培养是在带有缓冲板(水流调节壁)的或通常的锥形烧瓶中,通过1~2个阶段的育种工序开始的。在育种阶段的培养基中可并用碳源及氮源。在19~23℃下在保温培养箱中振动种烧瓶5天或振动到充分成长。成长了的种用于接种在第2种培养基或生产培养基上。在进行中间的发育工序时,用实质上相同的方法生长,将其一部分接种在生产培养基上。在恒定的温度下将接种了的烧瓶振荡培养几天,培养完成后离心分离或过滤烧瓶内的培养物。
在大量培养时,优选带在带有搅拌机、通气装置的广口发酵罐或槽中培养。为此,首先将营养培养基加热到121~130℃杀菌、冷却,接着通过上述的方法将预先成长的种接种在该杀过菌的培养基上。之后的培养是在19~23℃下通气搅拌进行的。此方法适宜得到多量化合物。
化合物(VI)和(VII)的生产,通过将预先过滤杀菌了的作为天冬氨酸激酶抑制剂的S-(2-氨基甲基)-L-半胱氨酸或其盐的水溶液在培养开始或培养中添加到杀过菌的培养基中而完成。
伴随培养过程中生产的化合物(VI)和(VII)的量,可通过采取一部分培养液用HPLC分析测定。化合物(VI)和(VII)的生产量,通常在3~15日可达到最高值。
培养完成后,通过以硅藻土作为过滤操作助剂的过滤操作或离心分离将培养液中的菌体成分分离,以HPLC分析作为指标,利用其物理化学的特性将存在于其滤液或上清液的化合物(VI)和(VII)进行纯化。作为硅藻土,例如优选使用硅藻土545(Celite Corporation社制)。滤液中存在的化合物(VI)和(VII)的纯化,作为吸附剂,例如,可通过活性炭或者作为吸附用树脂的大网状树脂XAD-2、XAD-4(ロ一ム·ァンド·ハ一ス社制)等或ダィャィォンHP-10、HP-20、CHP-20P、HP-50、SP207(三菱化学社制)等的单独使用或者将其组合使用完成的。通过将含有化合物(VI)和(VII)的溶液通过如上述的吸附剂层吸附不纯物并除去,或者吸附化合物(VI)和(VII)后,使用甲醇水、丙酮水、正丁醇水、氨水、含氨的甲醇水、含氨的丙酮水等洗脱,可分离化合物(VI)和(VII)。
进而,这样得到的化合物(VI)和(VII),可通过使用硅胶、フロリジル、コスモシル(ナカラィテスク社制)、ダィャィォンCHP-20P、SP207(三菱化学社制)等载体的吸附柱色谱;使用交联葡聚糖凝胶G-10(法玛西亚生物技术社制)、トョパ一ルHW40F(东曹社制)等的凝胶过滤色谱;使用ダゥェックス1、SBR-P(道化学社制)、ダィャィォンPA316(三菱化学社制)的阴离子交换色谱;和使用正向、逆向柱的HPLC等纯化出来。
通过将以上的分离、纯化方法单独或适当组合,根据情况反复使用,可分离纯化本发明的化合物(VI)和(VII)。
上面已经说明了本发明的化合物(I),其醚、酯和N-烷基衍生物,以及为制备它们的作为起始原料的化合物(VI)和(VII)的代表性的制备方法,但是并不限于这些制造方法,也可使用本领域技术人员已知的其他方法制备。
如以上得到的本发明的化合物(I)、其醚、酯和N-烷基衍生物是文献未公开的新化合物,对革兰氏阳性菌和革兰氏阴性菌显示优秀的抗菌活性。作为被期待优秀抗菌活性的革兰氏阳性菌,可列举例如,耻垢分枝杆菌、鸟分枝杆菌、胞内分枝杆菌、堪萨斯分枝杆菌、海分枝杆菌、瘰疬分枝杆菌、龟分枝杆菌、偶发分枝杆菌、结核分枝杆菌等抗酸菌(抗酸菌);枯草芽孢杆菌枯草菌;和金黄色葡萄球菌、酿脓链球菌、肺炎链球菌、粪肠球菌、屎肠球菌等球菌,作为革兰氏阴性菌可列举例如,粘膜炎拉莫氏菌和流感嗜血菌。这其中对抗酸菌的抗菌活性特别优秀,特别是对鸟分枝杆菌、胞内分枝杆菌、堪萨斯分枝杆菌、结核分枝杆菌抗菌活性特别优秀。
对革兰氏阳性菌和革兰氏阴性菌的生长抑制活性,可使用普通琼脂培养基(荣研化学社制)或心浸液琼脂培养基(Difco社制)的盘鉴定法(ディスクァッセィ法)测定。另外,可用在上述培养基中添加甘油的培养基同样地测定对于革兰阳性细菌放线菌属分枝菌(Mycobacteria)的生长抑制活性。
以上,说明了化合物(I)的生物活性的代表性评价方法,但评价方法不限于此,也可使用本领域技术人员已知的该方法以外的抗菌活性的评价方法。
将本发明化合物(I)、其药理上可接受醚、酯或N-烷基衍生物或其药理上可接受的盐作为药物使用时,可使用其本身或与适当的药理学容许的赋形剂、稀释剂等混合,以片剂、胶囊剂、颗粒剂、粉末剂、糖浆剂、注射剂、软膏剂、液剂、悬浮剂、气溶胶、糖衣片剂等方式给药。本发明的药物,可口服或非口服给药,优选作为有效成分的化合物(I)或其药理上可接受的盐送达肺或气管(包括口腔内和鼻腔内)给药。
这些各种制剂,可按照常法在主药中使用在赋形剂、结合剂、崩解剂、润滑剂、矫味矫臭剂、辅助溶解剂、悬浮剂、涂膜剂等的医药制剂技术领域中通常使用的已知辅助剂将它们制剂化。
在成形成片剂形态时,作为载体,可广泛使用在本领域以往公知的载体,例如可举出乳糖、白糖、氯化钠、葡萄糖、尿素、淀粉、碳酸钙、高岭土、结晶纤维素、硅酸等的赋形剂;水、乙醇、丙醇、单糖浆、葡萄糖液、淀粉液、明胶溶液、羧甲基纤维素、虫胶、甲基纤维素、磷酸钾、聚乙烯吡咯烷酮等的结合剂;干燥淀粉、藻酸钠、琼脂末、昆布多糖末、碳酸氢钠、碳酸钙、聚氧乙烯山梨糖醇酐脂肪酸酯、月桂基硫酸钠、硬脂酸单甘油酯、淀粉、乳糖等崩解剂;白糖、硬脂酸、可可油、加氢油等的崩解抑制剂;季铵盐、月桂基硫酸钠等吸收促进剂;甘油、淀粉等的保湿剂;淀粉、乳糖、高岭土、膨润土、胶体状硅酸等的吸附剂;精制滑石、硬脂酸盐、硼酸末、聚乙二醇等润滑剂等。另外,片剂可根据需要,作成施以通常的剂皮的片剂,例如糖衣片、明胶封囊片、肠溶包衣片、薄膜包衣片或二层片、多层片。
在成形丸剂形态时,作为载体,可广泛使用本领域以往公知的载体,例如可举出葡萄糖、乳糖、可可油酯、淀粉、硬化植物油、高岭土、滑石等的赋形剂;阿拉伯胶末、黄耆胶末、明胶、乙醇等的结合剂;昆布多糖琼脂等的崩解剂等。
在成形栓剂形态时,作为载体,可广泛使用本领域以往公知的载体,例如可举出聚乙二醇、可可油酯、高级醇、高级醇的酯类、明胶、半合成甘油等。
在配制注射剂时,优选将液剂和悬浮剂杀菌,且与血液是等渗的,在成形这些液剂、乳剂和悬浮剂的形态时,作为稀释剂可以使用本领域常用的稀释剂,例如可举出水、乙醇、丙二醇、乙氧基化异硬脂醇、聚氧化异硬脂醇、聚氧乙烯山梨糖醇酐脂肪酸酯类等。另外,此时,为了调制等渗性的溶液,在医药制剂中也可以含有充分量的食盐、葡萄糖、或甘油,也可以添加通常的助溶剂、缓冲剂、止痛剂等。
经肺给药使用液剂和悬浮剂时,化合物的溶液和悬浮液是水性的,一般例如,只用水(例如,无菌或不含发热物质的水)、或水和生理学上可接受的辅助溶剂(例如,乙醇、丙二醇、聚乙二醇、例如PEG400)来制备。这样的溶液或悬浮液中也可含有其他赋形剂、例如防腐剂(例如,氯化苄烷铵)、聚山梨酸酯等增溶剂/表面活性剂(例如,Tween80,Span80,氯化苄烷铵)、缓冲剂、等渗调节剂(例如,氯化钠)、吸收促进剂和增粘剂。悬浮液可进一步含有悬浮化试剂(例如,微晶纤维素、羧甲基纤维素钠)。液剂或悬浮剂可用一般方法,例如,滴液吸移管、吸量管或喷雾器直接对鼻腔或口腔给药。混合物可以一次剂量形式或多次给药量的形式提供。在后者时,优选设置给药量计量装置。在使用滴液吸移管或吸量管时,可使用对患者合适的给定体积的液剂或悬浮剂给药。在使用喷雾器时,通过例如计量喷雾器的手段完成。对气管或肺给药,可将化合物与氯氟碳(CFC),例如,二氯二氟甲烷、三氯氟甲烷或二氯四氟乙烷、二氧化碳或其他合适的气体等适宜抛射剂一起加压包装形成的气溶胶配合物完成。气溶胶优选含有卵磷脂等表面活性剂。药物的给药量可通过具备计量阀控制。
经肺给药使用粉末剂时,化合物可与干燥粉末,例如,乳糖、淀粉、淀粉衍生物(例如羟丙基甲基纤维素)、和聚乙烯吡咯烷酮(PVP)等合适的粉末基剂混合以粉末混合物的形式提供。优选粉末载体在鼻腔内形成凝胶。粉末组合物,例如可用明胶制的胶囊或软骨,或薄膜包装(粉末可通过吸入器从其中给药)等单位剂量形式给药。用于含有鼻内混合物的气管或肺给药混合物,化合物的粒径一般较小,例如5微米以下。这样的粒径可通过超微粉化等本领域公知的方法获得。如果需要,也可使用活性成分持续释放的混合物。
这些制剂,可进一步根据需要,含有着色剂、保护料、香料、风味剂、甜味剂等或其他药物。
对于含在上述药物制剂中的有效成分化合物的量,没有特别的限制,可广泛地适宜选择,但通常含有总组合物1~70重量%、优选的是1~30重量%的量是合适的。
对于上述药物制剂的给药方法没有特别的限制,根据各种制剂形态、患者的年龄、性别或其他的条件、疾病的程度等来决定。例如,在片剂、丸剂、液剂、悬浮剂、乳剂、颗粒剂和胶囊剂时,是经口给药。另外,在注射剂时,是单独或与葡萄糖、氨基酸等通常的补液混合静脉给药,进而根据需要单独给药于肌肉内、皮内、皮下或腹腔内。在栓剂时,给药于直肠。
其使用量,根据症状、年龄、体重、给药方法和剂形等而不同,但通常对于成人每天,作为上限是2000mg(优选的是100mg),作为下限是0.1mg(优选1mg,更优选10mg),根据症状,可分1次或数次进行给药。发明实施的最佳方案
下面列举实施例、试验例和制剂例对本发明进行具体说明。
实施例1(化合物编号6306)
将化合物(VI)57mg溶于甲醇1.5mL中,加入正丙胺99μL,在室温搅拌。2天后,减压蒸除溶剂,残渣用高效液相色谱法纯化(HPLC;Intersil PREP-ODS 30×250mm),用12%乙腈水溶液洗脱,冷冻干燥得到目的化合物41mg。
1H NMR(CD3OD)δppm:7.87(d,J=8.1Hz,1H),5.94(d,J=2.5Hz,1H),5.80(d,J=4.3Hz,1H),5.75(d,J=8.1Hz,1H),5.21(d,J=4.4Hz,1H),4.69(d,J=2.1Hz,1H),4.50(dd,J=2.0 and 5.2Hz,1H),4.38(t,J=3.9Hz,1H),4.24(t,J=4.6Hz,1H),4.03(m,1H),3.70(t,J=5.1Hz,1H),3.37(s,3H),3.24(m,2H),1.57(m,2H),0.93(t,J=7.5Hz,3H)。
IR(KBr)νcm-1:3360,2963,2935,2878,2835,1685,1535,1463,1387,1267,1139,1116,1094,1058,1023,978。
实施例2(化合物编号6321)
Figure A0081465303241
将化合物(VI)47mg溶于甲醇1mL中,加入正己胺132μL,在室温搅拌。2天后,减压蒸除溶剂,残渣用高效液相色谱纯化(HPLC;Inertsil PREP-ODS 30×250mm),用50%乙腈水溶液洗脱,冷冻干燥得到目的化合物23mg。
1H NMR(CD3OD)δppm:7.86(d,J=8.1Hz,1H),5.94(d,J=2.5Hz,1H),5.80(d,J=4.3Hz,1H),5.75(d,J=8.1Hz,1H),5.21(d,J=4.4Hz,1H),4.69(d,J=2.1Hz,1H),4.50(dd,J=1.8 and 5.4Hz,1H),4.38(t,J=3.9Hz,1H),4.23(t,J=4.6Hz,1H),4.03(m,1H),3.70(t,J=5.1Hz,1H),3.37(s,3H),3.25(m,2H),1.54(m,2H),1.33(m,6H),0.91(t,J=6.7Hz,3H)。
IR(KBr)νcm-1:3352,2956,2931,2872,2858,1685,1532,1464,1386,1267,1137,1115,1094,1058,992。
实施例3(化合物编号6336)
将化合物(VI)47mg溶于甲醇1mL中,加入正壬胺200μL,在50℃搅拌。4小时后,减压蒸除溶剂,残渣用高效液相色谱纯化(HPLC;Inertsil PREP-ODS 30×250mm),用50~80%乙腈水溶液洗脱,冷冻干燥得到目的化合物31mg。
1H NMR(CD3OD)δppm:7.86(d,J=8.1Hz,1H),5.94(d,J=2.9Hz,1H),5.81(d,J=4.2Hz,1H),5.75(d,J=8.1Hz,1H),5.21(d,J=4.6Hz,1H),4.69(d,J=2.1Hz,1H),4.50(dd,J=1.9 and 5.2Hz,1H),4.38(m,1H),4.23(t,J=4.6Hz,1H),4.03 (m,1H),3.70(t,J=5.1Hz,1H),3.38(s,3H),3.25(m,2H),1.54(m,2H),1.33(m,12H),0.90(t,J=6.6Hz,3H)。
IR(KBr)νcm-1:3339,2960,2926,2855,1686,1533,1464,1383,1262,1203,1095,1058,1025。
实施例4(化合物编号6346)
Figure A0081465303252
使用正十一烷基胺200μL,按照实施例3进行同样的合成,得到目的化合物10mg。
1H NMR(CD3OD)δppm:7.86(d,J=8.1Hz,1H),5.94(d,J=4.0Hz,1H),5.80(d,J=4.3Hz,1H),5.75(d,J=8.1Hz,1H),5.21(d,J=4.5Hz,1H),4.69(d,J=2.1Hz,1H),4.50(dd,J=2.0 and 5.2Hz,1H),4.38(t,J=4.0Hz,1H),4.23(t,J=4.7Hz,1H),4.03(m,1H),3.70(t,J=5.1Hz,1H),3.38(s,3H),3.25(m,2H),1.54(m,2H),1.33(m,16H),0.90(t,J=6.6Hz,3H)。
IR(KBr)νcm-1:3404,2955,2925,2854,1682,1531,1466,1408,1385,1266,1115,1095,1059。
实施例5(化合物编号6351)
使用正十二烷基胺200μL,按照实施例3进行同样的合成,得到目的化合物45mg。
1H NMR(CD3OD)δppm:7.86(d,J=8.1Hz,1H),5.94(d,J=2.9Hz,1H),5.81(d,J=4.4Hz,1H),5.75(d,J=8.1Hz,1H),5.21(d,J=4.4Hz,1H),4.70(d,J=2.2Hz,1H),4.50(m,1H),4.38(m,1H),4.23(t,J=4.4Hz,1H),4.04(t,J=4.4Hz,1H),3.70(t,J=5.1Hz,1H),3.38(s,3H),3.25(m,2H),1.54(m,2H),1.33(m,18H),0.90(t,J=7.0Hz,3H)。
IR(KBr)νcm-1:3350,2954,2925,2854,1686,1532,1465,1391,1267,1139,1116,1094,1057。
实施例6(化合物编号6361)
Figure A0081465303271
使用正十六烷基胺200μL,按照实施例3进行同样的合成,得到目的化合物11mg。
1H NMR(CD3OD)δppm:7.86(d,J=8.1Hz,1H),5.95(d,J=4.0Hz,1H),5.81(d,J=4.2Hz,1H),5.75(d,J=8.1Hz,1H),5.21(d,J=4.5Hz,1H),4.69(d,J=1.9Hz,1H),4.50(dd,J=1.9 and 5.2Hz,1H),4.38(t,J=3.9Hz,1H),4.23(t,J=4.7Hz,1H),4.03(t,J=4.3Hz,1H),3.70(t,J=5.1Hz,1H),3.38(s,3H),3.25(m,2H),1.54(m,2H),1.33(m,26H),0.90(t,J=6.8Hz,3H)。
IR(KBr)νcm-1:3349,2924,2853,1686,1531,1466,1385,1267,1115,1095,1057。
实施例7(化合物编号6371)
Figure A0081465303272
使用2-乙基己胺200μL,按照实施例3进行同样的合成,得到目的化合物26mg。
1H NMR(CD3OD)δppm:7.88(d,J=8.1Hz,1H),5.94(m,1H),5.81(d,J=4.4Hz,1H),5.75(d,J=8.1Hz,1H),5.21(d,J=4.5Hz,1H),4.69(d,J=2.0Hz,1H),4.50(dd,J=2.1 and 5.1Hz,1H),4.38(t,J=4.9Hz,1H),4.24(t,J=4.7Hz,1H),4.03(t,J=4.3Hz,1H),3.71(t,J=5.0Hz,1H),3.38(s,3H),3.25(m,2H),1.55(m,1H),1.33(m,8H),0.90(m,6H)。
IR(KBr)νcm-1:3365,2959,2930,2874,2860,1684,1530,1463,1385,1266,1139,1116,1093,1057。
实施例8(化合物编号6376)
Figure A0081465303281
使用环己基胺114μL,按照实施例3进行同样的合成,得到目的化合物12mg。
1H NMR(CD3OD)δppm:7.86(d,J=8.1Hz,1H),5.94(d,J=4.0Hz,1H),5.81(d,J=4.3Hz,1H),5.75(d,J=8.1Hz,1H),5.21(d,J=4.8Hz,1H),4.72(d,J=1.7Hz,1H),4.51(dd,J=1.8 and 5.1Hz,1H),4.34(t,J=3.9Hz,1H),4.23(t,J=4.7Hz,1H),4.02(t,J=4.2Hz,1H),3.75(m,1H),3.71(t,J=5.1Hz,1H),3.38(s,3H),1.90-1.15(m,9H)。
IR(KBr)νcm-1:3408,3352,2933,2855,1686,1527,1462,1386,1327,1267,1115,1090,1060,1021。
实施例9(化合物编号6381)
将化合物(VI)5g溶于丙酮500mL,加入2,2-二甲氧基丙烷52mL和1.25g大孔树脂15,在室温搅拌。19小时后,用硅藻土过滤,减压蒸除溶剂。残渣用硅胶柱(250g)色谱纯化,用4%甲醇-二氯甲烷洗脱,得到目的化合物3.82g。
1H NMR(CDCl3)δppm:8.42(br s,1H),7.70(d,J=8.1Hz,1H),7.13(brs,1H),6.40(d,J=4.4Hz,1H),5.94(d,J=5.1Hz,1H),5.80(brs,1H),5.74(dd,J=2.2 and 8.1Hz,1H),4.75(m,2H),4.56(d,J=8.1Hz,1H),4.53(s,1H),4.23(m,1H),4.15(m,1H),4.03(t,J=7.0Hz,1H),3.82(s,3H),3.58(s,3H),3.09(d,J=7.3Hz,1H),1.51(s,3H),1.46(s,3H)。(9-2)
Figure A0081465303292
将(9-1)的化合物3.82g溶于50%甲醇水溶液744mL,加入0.2N氢氧化钠水溶液186mL,在室温搅拌。10分钟后,用Dowex 50W×8(H+型500mL)纯化,用50%甲醇水溶液洗脱,得到目的化合物3.68g。
1H NMR(CD3OD)δppm:7.87(d,J=8.1Hz,1H),6.30(d,J=3.7Hz,1H),5.88(d,J=5.1Hz,1H),5.73(d,J=8.1Hz,1H),4.93(d,J=5.9Hz,1H),4.81(m,1H),4.63(d,J=2.2Hz,1H),4.56(m,1H),4.27(m,2H),4.00(t,J=5.1Hz,1H),3.50(s,3H),1.47(s,3H),1.45(s,3H)。(9-3)
将(9-2)化合物150mg溶于二甲基甲酰胺(DMF)2.6mL中,加入4-叔丁基环己基胺101μL和1-羟基苯并三唑(HOBT)61mg和二异丙基碳化二亚胺(DIPC)102μL,在室温搅拌。6小时后,减压蒸除溶剂,碱残渣溶于30mL乙酸乙酯,依次用各30mL的0.01N盐酸水溶液、饱和碳酸氢钠水溶液、饱和氯化钠水溶液洗净,用无水硫酸钠干燥,减压蒸除溶剂。将残渣溶于甲醇5.5mL,加入225mg的大孔树脂15,加热回流。2.5小时后过滤,减压蒸除溶剂,残渣用硅胶柱(8g)纯化,用5%甲醇-二氯甲烷洗脱,得到目的化合物(约7∶3的非对映异构体混合物)78mg。
1H NMR(CD3OD)δppm:7.89(d,J=8.1Hz,0.3H),7.86(d,J=8.1Hz,0.7H),5.95(d,J=2.5Hz,0.3H),5.93(d,J=4.0Hz,0.7H),5.81(d,J=4.4Hz,0.7H),5.79(d,J=3.9Hz,0.3H),5.75(d,J=8.1Hz,1H),5.27(d,J=4.4Hz,0.3H),5.20(d,J=4.6Hz,0.7H),4.72(d,J=1.7Hz,0.7H),4.61(d,J=1.7Hz,0.3H),4.51(dd,J=1.8 and 5.2Hz,0.7H),4.47(dd,J=1.9 and 5.5Hz,0.3H),4.38(m,1H),4.25(m,1H),4.02(m,1H),3.70(m,1H),3.64(s,0.9H),3.39(s,2.1H),1.97-1.82(m,3H),1.70-1.53(m,1H),1.40-0.97(m,5H),0.87(s,9H)。
IR(KBr)νcm-1:3408,2944,2864,1686,1524,1463,1385,1366,1329,1266,1190,1116,1090,1060,1022,987。
实施例10(化合物编号6386)
Figure A0081465303311
使用环庚基胺200μL代替4-叔丁基环己胺,按照实施例(9-3)进行同样的合成,得到目的化合物47mg。
1H NMR(CD3OD)δppm:7.87(d,J=8.1Hz,1H),5.93(d,J=4.0Hz,1H),5.81(d,J=4.2Hz,1H),5.75(d,J=8.1Hz,1H),5.21(d,J=4.7Hz,1H),4.71(d,J=2.1Hz,1H),4.51(dd,J=1.9 and 5.2Hz,1H),4.37(t,J=3.9 Hz,1H),4.24(t,J=4.7Hz,1H),4.02(m,1H),3.92(m,1H),3.70(m,1H),3.39(s,3H),1.89(m,2H),1.75-1.45(m,10H)。
IR(KBr)νcm-1:3403,2929,2857,1685,1525,1462,1385,1330,1267,1115,1091,1060,1018,994,978。
实施例11(化合物编号6396)
Figure A0081465303312
使用环十二烷基胺200μL代替4-叔丁基环己胺,按照实施例(9-3)进行同样的合成,得到目的化合物22mg。1H NMR(CD3OD)δppm:7.88(d,J=8.1Hz,1H),5.92(d,J=2.7Hz,1H),5.82(d,J=4.4Hz,1H),5.75(d,J=8.1Hz,1H),5.21(d,J=4.5Hz,1H),4.71(d,J=2.0Hz,1H),4.51(dd,J=2.0 and 5.0Hz,1H),4.38(t,J=3.9Hz,1H),4.24(t,J=4.7Hz,1H),4.02(t,J=4.2Hz,1H),3.65(m,1H),3.39(s,3H),1.73(m,2H),1.60-1.27(m,22H)。
IR(KBr)νcm-1:3363,2935,2864,1685,1529,1469,1446,1332,1262,1206,1186,1137,1095,1064,1024。
实施例12(化合物编号6401)
Figure A0081465303321
使用氨基甲基环己烷200μL,按照实施例3进行同样的合成,得到目的化合物28mg。
1H NMR(CD3OD)δppm:7.87(d,J=8.1Hz,1H),5.94(m,1H),5.81(d,J=4.4Hz,1H),5.75(d,J=8.1Hz,1H),5.21(d,J=4.4Hz,1H),4.69(d,J=2.1Hz,1H),4.50(dd,J=2.0 and 5.2Hz,1H),4.38(dd,J=3.3 and4.2Hz,1H),4.23(t,J=4.7Hz,1H),4.02(m,1H),3.70(t,J=5.0Hz,1H),3.38(s,3H),3.10(m,2H),2.81(t,J=7.3Hz,1H),1.98(m,2H),1.75-1.50(m,6H),1.22(m,2H)。
IR(KBr)νcm-1:3333,2925,2853,1684,1530,1462,1451,1386,1263,1137,1116,1093,1058。
实施例13(化合物编号6406)
使用2-(1-环己烯基)乙胺200μL,按照实施例3进行同样的合成,得到目的化合物30mg。
1H NMR(CD3OD)δppm:7.87(d,J=8.1Hz,1H),5.94(m,1H),5.80(d,J=4.2Hz,1H),5.75(d,J=8.1Hz,1H),5.48(brs,1H),5.20(d,J=4.7Hz,1H),4.65(d,J=2.1Hz,1H),4.48(m,1H),4.38(t,J=3.9Hz,1H),4.24(t,J=4.7Hz,1H),4.02(t,J=4.2Hz,1H),3.70(t,J=5.2Hz,1H),3.38(s,3H),3.30(m,2H),2.17(t,J=7.4Hz,1H),1.98(m,4H),1.65-1.53(m,4H)。
IR(KBr)νcm-1:3348,2929,2858,2836,1685,1530,1462,1389,1267,1137,1115,1093,1059。
实施例14(化合物编号6411)
使用顺-十八烯-9-基胺200μL,按照实施例3进行同样的合成,得到目的化合物32mg。
1H NMR(CD3OD)δppm:7.87(d,J=8.1Hz,1H),5.94(m,1H),5.81(d,J=4.1Hz,1H),5.75(d,J=8.1Hz,1H),5.34(t,J=4.5Hz,2H),5.21(d,J=4.4Hz,1H),4.69(d,J=2.1Hz,1H),4.50(dd,J=2.0 and 5.2Hz,1H),4.38(t,J=4.0Hz,1H),4.23(t,J=4.5Hz,1H),4.03(t,J=4.2Hz,1H),3.70(t,J=5.1Hz,1H),3.38(s,3H),2.79(t,J=7.4Hz,1H),2.00(m,6H),1.55(m,4H),1.32(m,20H),0.90(d,J=6.2Hz,3H)。
IR (KBr)νcm-1:3308,3006,2925,2854,1685,1533,1466,1385,1098。
实施例15(化合物编号6416)
使用3-(乙氧)丙基胺200μL,按照实施例3进行同样的合成,得到目的化合物35mg。
1H NMR(CD3OD)δppm:7.86(d,J=8.1Hz,1H),5.94(m,1H),5.79(d,J=1.9Hz,1H),5.75(d,J=8.1Hz,1H),5.21(d,J=4.2Hz,1H),4.65(d,J=1.6Hz,1H),4.49(dd,J=2.0 and 5.6Hz,1H),4.38(dd,J=3.2 and4.3Hz,1H),4.24(t,J=4.3Hz,1H),4.03(m,1H),3.69(t,J=5.2Hz,2H),3.50(m,4H),3.37(s,3H),1.89(m,2H),1.18(tJ=7.2Hz,3H)。
IR(KBr)νcm-1:3351,2972,2933,2874,1685,1532,1462,1386,1267,1221,1136,1115,1058,1023。
实施例16(化合物编号6421)
Figure A0081465303342
使用3-(甲硫基)丙基胺200μL,按照实施例3进行同样的合成,得到目的化合物30mg。
1H NMR(CD3OD)δppm:7.87(d,J=8.1Hz,1H),5.95(m,1H),5.79(d,J=4.0Hz,1H),5.75(d,J=8.1Hz,1H),5.21(d,J=4.4Hz,1H),4.68(d,J=2.1Hz,1H),4.50(dd,J=2.0 and 5.6Hz,1H),4.38(dd,J=3.2 and4.3Hz,1H),4.24(t,J=4.6Hz,1H),4.04(t,J=4.2Hz,1H),3.70(t,J=5.2Hz,1H),3.38(m,2H),3.37(s,3H),2.52(tJ=7.4Hz,2H),2.08(s,3H),1.84(m,2H)。
IR(KBr)νcm-1:3351,2925,1685,1532,1462,1390,1267,1137,1115,1094,1057,976。
实施例17(化合物编号6431)
Figure A0081465303351
使用2,2-(二乙氧)乙基胺200μL,按照实施例3进行同样的合成,得到目的化合物21mg。
1H NMR(CD3OD)δppm:7.88(d,J=8.1Hz,1H),5.97(m,1H),5.81(d,J=4.3Hz,1H),5.75(d,J=8.1Hz,1H),5.22(d,J=4.7Hz,1H),4.66(d,J=2.1Hz,1H),4.62(t,J=5.3Hz,1H),4.50(dd,J=2.0 and 5.2Hz,1H),4.38(t,J=4.0Hz,1H),4.24(t,J=4.7Hz,1H),4.02(m,1H),3.70(m,3H),3.55(m,2H),3.47-3.33(m,2H),3.37(s,3H),1.20(m,6H)。
IR(KBr)νcm-1:3350,2877,2935,1686,1531,1462,1385,1268,1122,1091,1058。
实施例18(化合物编号6436)
使用2-羟基乙基胺200μL,按照实施例3进行同样的合成,得到目的化合物28mg。
1H NMR(CD3OD)δppm:7.87(d,J=8.1Hz,1H),5.97(d,J=2.4Hz,1H),5.81(d,J=4.4Hz,1H),5.75(d,J=8.1Hz,1H),5.21(d,J=4.6Hz,1H),4.69(d,J=2.1Hz,1H),4.51(dd,J=1.8 and 5.1Hz,1H),4.38(t,J=4.0Hz,1H),4.24(t,J=4.7Hz,1H),4.02(m,1H),3.73(t,J=5.1Hz,1H),3.63(m,4H),3.37(s,3H)。
IR(KBr)νcm-1:3337,2937,1684,1535,1462,1426,1394,1361,1264,1139,1115,1092,1058。
实施例19(化合物编号6441)
使用1,2-氨基乙烷200μL,按照实施例3进行同样的合成,得到目的化合物26mg。
1H NMR(CD3OD)δppm:7.85(d,J=8.1Hz,1H),5.98(m,1H),5.77(d,J=3.8Hz,1H),5.74(d,J=8.1Hz,1H),5.23(d,J=4.2Hz,1H),4.65(d,J=1.8Hz,1H),4.48(dd,J=2.0 and 5.7Hz,1H),4.40(dd,J=3.2 and4.3Hz,1H),4.25(t,J=3.9Hz,1H),4.06(m,1H),3.70(m,2H),3.37(s,3H),2.95(m,2H)。
IR(KBr)νcm-1:3305,2940,1682,1532,1464,1428,1396,1265,1203,1180,1136,1095,1060,1021 。
实施例20(化合物编号6451)
使用5-羟基戊基胺200μL,按照实施例3进行同样的合成,得到目的化合物19mg。
1H NMR(CD3OD)δppm:7.86(d,J=8.1Hz,1H),5.94(m,1H),5.80(d,J=4.2Hz,1H),5.75(d,J=8.1Hz,1H),5.21(d,J=4.4Hz,1H),4.69(d,J=2.0Hz,1H),4.50(dd,J=1.9 and 5.4Hz,1H),4.38(dd,J=3.3 and4.3Hz,1H),4.23(t,J=4.6Hz,1H),4.03(m,1H),3.55(m,2H),3.38(s,3H),2.75(t,J=7.0Hz,2H),1.55(m,6H)。
IR(KBr)νcm-1:3336,2935,1684,1644,1532,1461,1391,1264,1139,1115,1091,1057。
实施例21(化合物编号6456)
Figure A0081465303372
使用2-苯基乙胺200μL,按照实施例3进行同样的合成,得到目的化合物35mg。1H NMR(CD3OD)δppm:7.87(d,J=8.1Hz,1H),7.30(m,2H),7.22(m,3H),5.96(m,1H),5.80(d,J=4.1Hz,1H),5.75(d,J=8.1Hz,1H),5.20(d,J=4.7Hz,1H),4.64(d,J=2.0Hz,1H),4.50(dd,J=2.0 and 5.3Hz,1H),4.38(dd,J=3.3 and 4.2Hz,1H),4.23(t,J=4.5Hz,1H),4.02(t,J=4.1Hz,1H),3.69(t,J=5.1Hz,1H),3.48(m,2H),3.35(s,3H),2.84(t,J=7.6Hz,2H)。
IR(KBr)νcm-1:3392,3368,2932,1685,1532,1497,1458,1390,1267,1136,1115,1094,1059,1029。
实施例22(化合物编号6461)
Figure A0081465303381
使用2-(4-甲基苯基)乙胺200μL,按照实施例3进行同样的合成,得到目的化合物29mg。
1H NMR(CD3OD)δppm:7.86(d,J=8.1Hz,1H),7.10(s,4H),5.96(m,1H),5.80(d,J=4.1Hz,1H),5.75(d,J=8.1Hz,1H),5.19(d,J=4.7Hz,1H),4.64(d,J=2.1Hz,1H),4.49(dd,J=2.0 and 5.5Hz,1H),4.38(t,J=3.9Hz,1H),4.23(t,J=4.5Hz,1H),4.02(m,1H),3.69(t,J=5.1Hz,1H),3.45(m,2H),3.34(s,3H),2.79(t,J=6.6Hz,2H),2.29(s,3H)。
IR(KBr)νcm-1:3400,2930,1684,1531,1517,1463,1385,1267,1137,1115,1095,1060。
实施例23(化合物编号6466)
使用2-(2-甲氧苯基)乙胺200μL,按照实施例3进行同样的合成,得到目的化合物28mg。
1H NMR(CD3OD)δppm:7.86(d,J=8.1Hz,1H),7.19(t,J=7.8Hz,1H),7.14(d,J=7.4Hz,1H),6.93(d,J=8.4Hz,1H),6.87(t,J=7.4Hz,1H),5.95(m,1H),5.80(d,J=4.2Hz,1H),5.75(d,J=8.1Hz,1H),5.19(d,J=4.5Hz,1H),4.63(d,J=2.0Hz,1H),4.48(dd,J=1.9 and 5.6Hz,1H),4.38(t,J=4.0Hz,1H),4.22(t,J=4.5Hz,1H),4.02(m,1H),3.83(s,3H),3.66(t,J=5.2Hz,1H),3.46(m,2H),3.34(s,3H),2.86(m,2H)。
IR(KBr)νcm-1:3365,2933,1685,1531,1495,1464,1389,1266,1245,1118,1054,1024。
实施例24(化合物编号6476)
使用2-(4-甲氧苯基)乙胺200μL,按照与实施例3同样进行合成,得到目的化合物35mg。
1H NMR(CD3OD)δppm:7.87(d,J=8.1Hz,1H),7.14(d,J=8.7Hz,2H),6.85(d,J=8.7Hz,2H),5.96(m,1H),5.80(d,J=4.0Hz,1H),5.75(d,J=8.1Hz,1H),5.20(d,J=4.6Hz,1H),4.64(d,J=1.7Hz,1H),4.50(dd,J=2.0 and 5.3Hz,1H),4.38(m,1H),4.23(t,J=4.6Hz,1H),4.02(t,J=4.2Hz,1H),3.76(s,3H),3.69(t,J=5.2Hz,1H),3.45(m,2H),3.34(s,3H),2.76(m,2H)。
IR(KBr)νcm-1:3342,2935,1685,1513,1461,1391,1361,1301,1247,1178,1138,1115,1093,1059,1031。
实施例25(化合物编号6481)
使用2-(3,4-二甲氧苯基)乙胺200μL,按照与实施例3同样进行合成,得到目的化合物39mg。
1H NMR(CD3OD)δppm:7.86(d,J=8.1Hz,1H),6.88(d,J=8.1Hz,1H),6.84(d,J=1.7Hz,1H),6.77(dd,J=1.7 and 8.1Hz,1H),5.96(m,1H),5.79(d,J=4.1Hz,1H),5.75(d,J=8.1Hz,1H),5.20(d,J=4.4Hz,1H),4.64(d,J=2.1Hz,1H),4.49(dd,J=1.9 and 5.3Hz,1H),4.38(t,J=3.9Hz,1H),4.23(t,J=4.5Hz,1H),4.02(t,J=4.2Hz,1H),3.82(s,3H),3.80(s,3H),3.68(t,J=5.2Hz,1H),3.45(m,2H),3.33(s,3H),2.78(t,J=7.4Hz,2H)。
IR(KBr)νcm-1:3350,2937,2837,1685,1516,1464,1418,1389,1263,1237,1141,1116,1094,1059,1026。
实施例26(化合物编号6486)
使用2-(4-氟苯基)乙胺200μL,按照与实施例3同样进行合成,得到目的化合物33mg。
1H NMR(CD3OD)δppm:7.87(d,J=8.1Hz,1H),7.23(m,2H),7.01(t,J=8.8Hz,2H),5.95(m,1H),5.80(d,J=4.1Hz,1H),5.75(d,J=8.1Hz,1H),5.20(d,J=4.5Hz,1H),4.65(d,J=1.7Hz,1H),4.50(dd,J=2.0and 5.3Hz,1H),4.38(dd,J=3.3 and 4.2Hz,1H),4.23(t,J=4.6Hz,1H),4.03(t,J=4.2Hz,1H),3.69(t,J=5.1Hz,1H),3.45(m,2H),3.35(s,3H),2.83(t,J=7.5Hz,2H)。
IR(KBr)νcm-1:3349,2935,1685,1531,1510,1463,1391,1266,1222,1137,1116,1098,1059。
实施例27(化合物编号6496)
Figure A0081465303411
使用2-(3-氯苯基)乙胺200μL,按照与实施例3同样进行合成,得到目的化合物33mg。
1H NMR(CD3OD)δppm:7.86(d,J=8.1Hz,1H),7.30-7.15(m,4H),5.96(m,1H),5.80(d,J=4.2Hz,1H),5.75(d,J=8.1Hz,1H),5.20(d,J=4.4Hz,1H),4.65(d,J=2.1Hz,1H),4.50(dd,J=2.0 and 5.3Hz,1H),4.38(t,J=3.9Hz,1H),4.23(t,J=4.6Hz,1H),4.02(m,1H),3.69(t,J=5.2Hz,1H),3.45(m,2H),3.35(s,3H),2.84(t,J=7.4Hz,2H)。
IR(KBr)νcm-1:3401,2934,1684,1599,1574,1530,1463,1389,1267,1136,1116,1096,1059。
实施例28(化合物编号6506)
Figure A0081465303421
使用2-(2,4-二氯苯基)乙胺200μL,按照与实施例3同样进行合成,得到目的化合物33mg。
1H NMR(CD3OD)δppm:7.87(d,J=8.1Hz,1H),7.44(d,J=1.8Hz,1H),7.29(m,2H),5.94(d,J=2.5Hz,1H),5.80(d,J=4.1Hz,1H),5.75(d,J=8.1Hz,1H),5.20(d,J=4.5Hz,1H),4.66(d,J=2.0Hz,1H),4.49(dd,J=1.8 and 5.4Hz,1H),4.38(t,J=3.9Hz,1H),4.23(t,J=4.4Hz,1H),4.02(t,J=4.2Hz,1H),3.69(t,J=5.2Hz,1H),3.50(m,2H),3.35(s,3H),2.98(m,2H)。
IR(KBr)νcm-1:3402,2931,1684,1591,1530,1473,1386,1268,1115,1054。
实施例29(化合物编号6511)
使用2-(4-羟基苯基)乙胺200μL,按照与实施例3同样进行合成,得到目的化合物43mg。
1H NMR(CD3OD)δppm:7.88(d,J=8.1Hz,1H),7.42-7.25(m,4H),5.98(d,J=3.5Hz,1H),5.83(t,J=4.9Hz,1H),5.75(d,J=8.1Hz,1H),5.20(t,J=5.1Hz,1H),4.75(m,1H),4.67(m,1H),4.52(m,1H),4.48(m,1H),4.26(m,1H),4.00(m,1H),3.75(m,1H),3.55(m,2H),3.40 and 3.35(2s,3H),3.33(m,1H)。
IR(KBr)νcm-1:3339,2934,1681,1532,1495,1455,1389,1267,1199,1138,1115,1094,1062,1027。
实施例30(化合物编号6516)
Figure A0081465303431
使用2,2-二苯基乙胺200μL,按照与实施例3同样进行合成,得到目的化合物22mg。
1H NMR(CD3OD)δppm:7.84(d,J=8.1Hz,1H),7.28(m,8H),7.20(m,2H),5.91(d,J=2.4Hz,1H),5.80(d,J=4.3Hz,1H),5.73(d,J=8.1Hz,1H),5.11(d,J=4.8Hz,1H),4.53(d,J=2.1Hz,1H),4.45(dd,J=2.1 and5.2Hz,1H),4.35(m,2H),4.20(t,J=4.5Hz,1H),3.95(m,2H),3.85(m,1H),3.63(t,J=5.1Hz,1H),3.31(s,3H)。
IR(KBr)νcm-1:3416,3062,3028,2934,1685,1527,1495,1454,1385,1268,1115,1092,1059。
实施例31(化合物编号6521)
Figure A0081465303432
使用2-(吡啶-2-基)乙胺200μL,按照与实施例3同样进行合成,得到目的化合物25mg。
1H NMR(CD3OD)δppm:8.48(d,J=5.4Hz,1H),7.87(d,J=8.2Hz,1H),7.78(m,1H),7.34(d,J=8.0Hz,1H),7.28(m,1H),5.94(m,1H),5.80(d,J=4.3Hz,1H),5.75(d,J=8.2Hz,1H),5.20(d,J=4.5Hz,1H),4.65(d,J=1.7Hz,1H),4.49(dd,J=2.0 and 5.3Hz,1H),4.38(t,J=3.8Hz,1H),4.23(t,J=4.7Hz,1H),4.02(m,1H),3.70(t,J=5.1Hz,1H),3.64(m,2H),3.34(s,3H),3.02(t,J=7.0Hz,2H)。
IR(KBr)νcm-1:3367,2935,1684,1596,1570,1531,1462,1438,1387,1265,1139,1116,1094,1058。
实施例32(化合物编号6526)
使用2-(噻吩-2-基)乙胺200μL,按照与实施例3同样进行合成,得到目的化合物29mg。
1H NMR(CD3OD)δppm:7.87(d,J=8.1Hz,1H),7.21(d,J=5.1Hz,1H),6.93(dd,J=3.7 and 5.1Hz,1H),6.88(d,J=3.7Hz,1H),5.96(d,J=4.0Hz,1H),5.81(d,J=4.3Hz,1H),5.75(d,J=8.1Hz,1H),5.20(d,J=4.8Hz,1H),4.66(d,J=2.1Hz,1H),4.50(dd,J=1.9 and 5.2Hz,1H),4.39(t,J=4.0Hz,1H),4.24(t,J=4.6Hz,1H),4.02(m,1H),3.71(t,J=5.1Hz,1H),3.52(m,2H),3.35(s,3H),3.07(t,J=7.3Hz,2H)。
IR(KBr)3335,2933,1685,1529,1462,1390,1266,1115,1094,1059。
实施例33(化合物编号6531)
Figure A0081465303451
使用苄胺109μL,按照与实施例3同样进行合成,得到目的化合物28mg。
1H NMR(CD3OD)δppm:7.86(d,J=8.1Hz,1H),7.31(m,4H),7.24(m,1H),5.98(m,1H),5.79(d,J=4.3Hz,1H),5.75(d,J=8.1Hz,1H),5.21(d,J=4.5Hz,1H),4.68(d,J=2.1Hz,1H),4.46(m,2H),4.35(m,1H),4.21(t,J=4.5Hz,1H),4.04(t,J=4.4Hz,1H),3.67(t,J=5.1Hz,1H),3.20(s,3H)。
IR(KBr)νcm-1:3350,2929,1685,1529,1457,1391,1267,1115,1093,1059,1022。
实施例34(化合物编号6536)
使用2-甲基苄胺200μL,按照与实施例3同样进行合成,得到目的化合物29mg。
1H NMR(CD3OD)δppm:7.87(d,J=8.1Hz,1H),7.24(m,1H),7.15(m,3H),5.98(d,J=3.9Hz,1H),5.80(d,J=4.3Hz,1H),5.75(d,J=8.1Hz,1H),5.22(d,J=4.7Hz,1H),4.69(d,J=2.0Hz,1H),4.48(m,3H),4.40(m,1H),4.22(t,J=4.6Hz,1H),4.03(m,1H),3.69(t,J=5.1Hz,1H),3.21(s,3H),2.33(s,3H)。
IR(KBr)νcm-1:3349,2935,1685,1527,1462,1386,1268,1116,1091,1058。
实施例35(化合物编号6546)
使用4-氟苄胺200μL,按照与实施例3同样进行合成,得到目的化合物13mg。
1H NMR(CD3OD)δppm:7.85(d,J=8.1Hz,1H),7.34(m,2H),7.05(m,2H),5.98(m,1H),5.78(d,J=4.2Hz,1H),5.75(d,J=8.1Hz,1H),5.22(d,J=4.4Hz,1H),4.67(d,J=2.0Hz,1H),4.43(d,J=3.5Hz,2H),4.39(dd,J=3.2 and 4.3Hz,1H),4.22(t,J=4.5Hz,1H),4.04(t,J=4.3Hz,1H),3.66(t,J=5.1Hz,1H),3.20(s,3H)
IR(KBr)νcm-1:3351,2935,1684,1526,1510,1462,1416,1387,1359,1266,1222,1137,1115,1095,1059,1020。
实施例36(化合物编号6561)
Figure A0081465303462
使用3,4,5-三甲氧苄胺200μL,按照与实施例3同样进行合成,得到目的化合物29mg。
1H NMR(CD3OD)δppm:7.85(d,J=8.1Hz,1H),6.65(s,2H),5.99(m,1H),5.77(d,J=4.0Hz,1H),5.75(d,J=8.1Hz,1H),5.22(d,J=4.3Hz,1H),4.66(d,J=2.0Hz,1H),4.47-4.34(m,4H),4.21(t,J=4.3Hz,1H),4.05(t,J=4.4Hz,1H),3.82(s,6H),3.73(s,3H),3.64(t,J=5.5Hz,1H),3.18(s,3H)。
IR(KBr)νcm-1:3349,2939,2838,1686,1594,1527,1507,1462,1423,1387,1357,1330,1265,1237,1125,1058,1020。
实施例37(化合物编号6566)
Figure A0081465303471
使用3,4-亚甲基二氧苄胺200μL,按照与实施例3同样进行合成,得到目的化合物31mg。
1H NMR(CD3OD)δppm:7.85(d,J=8.1Hz,1H),6.75(m,3H),5.97(m,1H),5.90(s,2H),5.79(d,J=4.3Hz,1H),5.74(d,J=8.1Hz,1H),5.20(d,J=4.5Hz,1H),4.67(d,J=2.1Hz,1H),4.47(dd,J=1.8 and 5.4Hz,1H),4.41-4.31(m,3H),4.20(t,J=4.6Hz,1H),4.02(m,1H),3.66(t,J=5.1Hz,1H),3.23(s,3H)。
IR(KBr)νcm-1:3350,2935,1685,1528,1503,1491,1462,1444,1386,1253,1115,1096,1056,1039。
实施例38(化合物编号6571)
Figure A0081465303472
(38-1)
Figure A0081465303481
将化合物(VI)1.5g溶于环戊酮75mL中,加入1,1-二甲氧环戊烷16.5g和350mg的大网树脂15,在室温搅拌。3小时后,滤除不溶物,减压蒸除溶剂。残渣用硅胶柱(86g)纯化,用3%甲醇-二氯甲烷洗脱,得到目的化合物1.31g。
1H NMR(CDCl3)δppm:8.94(br s,1H),7.71(d,J=8.1Hz,1H),8.18(brs,1H),6.39(d,J=4.4Hz,1H),6.31(m,1H),5.94(d,J=4.9Hz,1H),5.75(d,J=8.1Hz,1H),4.70(m,1H),4.60(m,2H),4.52(m,1H),4.25(t,J=5.3Hz,1H),4.15(m,1H),3.99(m,1H),3.82(s,3H),3.58(s,3H),2.05-1.60(m,8H)。
(38-2)
Figure A0081465303482
将实施例(38-1)的化合物1.31g溶于甲醇200mL和水200mL的混合溶剂,加入0.2N氢氧化钠水溶液100mL,在室温搅拌。4分钟后,将反应液用Dowex50W×8(H+型)纯化,用甲醇-水(1∶1)洗脱,得到目的化合物。
(38-3)
Figure A0081465303491
将实施例(38-2)的化合物80mg溶于DMF1.4mL中,加入L-(-)-α-苯乙胺38μL和HOBT 33mg和DIPC54μL,在室温搅拌。2小时后加入甲醇1mL,减压蒸除溶剂。将残渣溶于33mL二氯甲烷,加入三氟乙酸(TFA)1.76mL,在室温搅拌。5.5小时后,减压蒸除溶剂,残渣用硅胶柱(9g)纯化,用7%甲醇-二氯甲烷洗脱,得到目的化合物79mg。
1H NMR(CD3OD)δppm:7.85(d,J=8.1Hz,1H),7.35(m,4H),7.22(m,1H),5.95(m,1H),5.78(d,J=4.4Hz,1H),5.74(d,J=8.1Hz,1H),5.24(d,J=4.6Hz,1H),5.14(quartet,J=6.9Hz,1H),4.71(d,J=2.0Hz,1H),4.47(dd,J=1.7 and 5.1Hz,1H),4.38(t,J=3.9Hz,1H),4.18(t,J=4.7Hz,1H),4.03(m,1H),3.61(t,J=5.0Hz,1H),3.02(s,3H),1.52(d,J=7.2Hz,3H)。
IR(KBr)νcm-1:03339,2927,2853,1685,1524,1462,1386,1332,1269,1205,1137,1117,1060,1022。
实施例39(化合物编号6576)
使用2-氨基甲基萘200μL,按照与实施例3同样进行合成,得到目的化合物28mg。
1H NMR(CD3OD)δppm:7.85(m,3H),7.50(m,4H),6.02(d,J=3.9Hz,1H),5.77(d,J=4.3Hz,1H),5.73(d,J=8.1Hz,1H),5.19(d,J=4.9Hz,1H),5.00(d,J=15Hz,1H),4.90(d,J=15.0Hz,1H),4.65(d,J=2.1Hz,1H),4.43(dd,J=2.0 and 5.2Hz,1H),4.40(t,J=3.5Hz,1H),4.16(t,J=4.6Hz,1H),4.02(t,J=4.9Hz,1H),3.62(t,J=5.1Hz,1H),3.05(s,3H)。
IR(KBr)νcm-1:3349,2935,1685,1527,1462,1397,1266,1116,1094,1060,1023。
实施例40(化合物编号6581)
使用2-氨基甲基呋喃200μL,按照与实施例3同样进行合成,得到目的化合物26mg。
1H NMR(CD3OD)δppm:7.85(m,3H),7.40(d,J=2.4Hz,1H),6.33(m,1H),6.27(m,1H),5.98(m,1H),5.80(d,J=4.4Hz,1H),5.75(d,J=8.1Hz,1H),5.20(d,J=4.7Hz,1H),4.68(d,J=2.1Hz,1H),4.51-4.37(m,4H),4.21(t,J=4.7Hz,1H),4.02(m,1H),3.68(t,J=5.1Hz,1H),3.27(s,3H)。
IR(KBr)νcm-1:3365,2934,1685,1528,1463,1391,1332,1268,1140,1115,1093,1059,1019。
实施例41(化合物编号6586)
使用2-氨基甲基噻吩200μL,按照与实施例3同样进行合成,得到目的化合物22mg。
1H NMR(CD3OD)δppm:7.85(d,J=8.1Hz,1H),7.27(d,J=5.1Hz,1H),7.02(m,1H),6.92(m,1H),5.98(d,J=2.4Hz,1H),5.79(d,J=4.4Hz,1H),5.75(d,J=8.1Hz,1H),5.20(d,J=4.4Hz,1H),4.67(d,J=2.2Hz,1H),4.65(d,J=15.0Hz,1H),4.59(d,J=15.0Hz,1H),4.47(dd,J=1.7 and 5.1Hz,1H),4.39(t,J=4.9Hz,1H),4.20(t,J=4.6Hz,1H),4.02(m,1H),3.66(t,J=5.1Hz,1H),3.21(s,3H)。
IR(KBr)νcm-1:3334,2930,1684,1522,1462,1390,1267,1223,1115,1092,1059。
实施例42(化合物编号6591)
使用2-氨基甲基吡啶108μL代替4-叔丁基环己胺,按照与实施例(9-3)同样进行合成,得到目的化合物79mg。
1H NMR(CD3OD)δppm:8.49(d,J=5.2Hz,1H),7.88(d,J=8.1Hz,1H),7.80(m,1H),7.42(m,1H),7.30(m,1H),6.01(m,1H),5.81(d,J=4.4Hz,1H),5.75(d,J=8.1Hz,1H),5.25(d,J=4.5Hz,1H),4.70(d,J=2.0Hz,1H),4.59(s,2H),4.51(dd,J=2.0 and 5.2 Hz,1H),4.41(t,J=4.0Hz,1H),4.26(t,J=4.5Hz,1H),4.02(m,1H),3.75(t,J=5.0Hz,1H),3.30(s,3H)。
IR(KBr)νcm-1:3334,2932,1684,1597,1572,1528,1463,1438,1392,1266,1139,1116,1095,1059,1021。
实施例43(化合物编号2)
使用苯胺108μL代替L-(-)-α-苯乙胺,与实施例(38-2)的化合物50mg,按照与实施例(38-3)同样进行合成,用高效液相色谱纯化(HPLC;Inertsil PREP-ODS 30×250mm),用15%乙腈水溶液洗脱,冷冻干燥得到目的化合物22mg。
1H NMR(CD3OD)δppm:7.87(d,J=8.1Hz,1H),7.64(d,J=8.8Hz,2H),7.34(t,J=7.5Hz,2H),7.15(t,J=7.3Hz,1H),6.09(m,1H),5.77(d,J=3.7Hz,1H),5.75(d,J=8.1Hz,1H),5.30(d,J=4.3Hz,1H),4.85(m,1H),4.52(dd,J=1.8 and 6.0Hz,1H),4.45(m,1H),4.26(t,J=4.2Hz,1H),4.10(m,1H),3.75(t,J=5.5Hz,1H),3.28(s,3H)。
IR(KBr)νcm-1:3339,2936,1685,1599,1534,1497,1462,1444,1391,1323,1269,1113,1060,1018,977。
实施例44(化合物编号142)
使用4-乙基苯胺57μL代替L-(-)-α-苯乙胺,与实施例(38-2)的化合物120mg,按照与实施例(38-3)同样进行合成,用高效液相色谱纯化(HPLC;Inertsil PREP-ODS 30×250mm),用30%乙腈水溶液洗脱,冷冻干燥得到目的化合物48mg。
1H NMR(CD3OD)δppm:7.86(d,J=8.1Hz,1H),7.53(d,J=8.5Hz,2H),7.18(d,J=8.5Hz,2H),6.14(m,1H),5.77(d,J=3.7Hz,1H),5.75(d,J=8.1Hz,1H),5.29(d,J=4.4Hz,1H),4.85(m,1H),4.52(dd,J=1.9and 6.1Hz,1H),4.44(m,1H),4.26(t,J=4.4Hz,1H),4.08(t,J=4.3Hz,1H),3.75(t,J=5.5Hz,1H),3.28(s,3H),2.62(quartet,J=7.6Hz,2H),1.22(t,J=7.6Hz,3H)。
IR(KBr)νcm-1:3341,2963,2932,1685,1594,1527,1462,1413,1392,1319,1268,1112,1060,1019,977。
实施例45(化合物编号3012)
使用4-氟苯胺43μL代替L-(-)-α-苯乙胺,与实施例(38-2)的化合物120mg,按照与实施例(38-3)同样进行合成,用高效液相色谱纯化(HPLC;Inertsil PREP-ODS 30×250mm),用30%乙腈水溶液洗脱,冷冻干燥得到目的化合物122mg。
1H NMR(CD3OD)δppm:7.86(d,J=8.1Hz,1H),7.65(m,2H),7.08(m,2H),6.08(m,1H),5.77(d,J=3.7Hz,1H),5.75(d,J=8.1Hz,1H),5.30(d,J=4.3Hz,1H),4.85(m,1H),4.51(dd,J=1.9 and 6.2Hz,1H),4.44(dd,J=3.2 and 4.3Hz,1H),4.25(dd,J=3.8 and 4.8Hz,1H),4.10(m,1H),3.74(t,J=5.5Hz,1H),3.28(s,3H)。
IR(KBr)νcm-1:3342,2969,2936,1686,1624,1576,1533,1510,1464,1410,1391,1326,1314,1269,1215,1129,1115,1060,1018。
实施例46(化合物编号3152)
使用4-溴苯胺79mg代替L-(-)-α-苯乙胺,与实施例(38-2)的化合物120mg,按照与实施例(38-3)同样进行合成,用高效液相柱色谱纯化(HPLC;Inertsil PREP-ODS 30×250mm),用30%乙腈水溶液洗脱,冷冻干燥得到目的化合物52mg。
1H NMR(CD3OD)δppm:7.86(d,J=8.1Hz,1H),7.61(d,J=8.9Hz,2H),7.48(d,J=8.9Hz,2H),6.08(m,1H),5.76(d,J=3.7Hz,1H),5.75(d,J=8.1Hz,1H),5.30(d,J=4.0Hz,1H),4.85(m,1H),4.51(dd,J=2.0and 6.0Hz,1H),4.44(dd,J=3.2 and 4.3Hz,1H),4.25(dd,J=3.7 and4.8Hz,1H),4.09(m,1H),3.73(m,1H),3.27(s,3H)。
IR(KBr)νcm-1:3400,2933,1685,1591,1527,1490,1464,1397,1310,1271,1243,1113,1061,1017,977。
实施例47(化合物编号2452)
使用3-苄氧苯胺90mg代替L-(-)-α-苯乙胺,与实施例(38-2)的化合物120mg,按照实施例(38-3)进行同样的合成,用高效液相柱色谱纯化(HPLC;Inertsil PREP-ODS 30×250mm),用30%乙腈水溶液洗脱,冷冻干燥得到目的化合物106mg。
1H NMR(CD3OD)δppm:7.86(d,J=8.1Hz,1H),7.44(m,3H),7.37(m,2H),7.30(m,1H),7.23(m,2H),6.80(m,1H),6.09(m,1H),5.77(d,J=3.6Hz,1H),5.75(d,J=8.1Hz,1H),5.29(d,J=4.3Hz,1H),5.08(s,2H),4.85(m,1H),4.52(dd,J=1.9 and 6.2Hz,1H),4.44(t,J=4.3Hz,1H),4.25(t,J=4.2Hz,1H),4.08(m,1H),3.74(t,J=5.5Hz,1H),3.26(s,3H)。
IR(KBr)νcm-1:3342,2929,1685,1605,1537,1493,1456,1444,1426,1386,1269,1206,1183,1157,1138,1115,1060,1022。
实施例48(化合物编号5462)
使用2-硝基苯胺63mg代替L-(-)-α-苯乙胺,与实施例(38-2)的化合物120mg,按照与实施例(38-3)同样进行合成,用高效液相色谱纯化(HPLC;Inertsil PREP-ODS 30×250mm),用30%乙腈水溶液洗脱,冷冻干燥得到目的化合物8mg。
1H NMR(CD3OD)δppm:8.73(d,J=8.6Hz,1H),8.28(d,J=8.6Hz,1H),7.96(d,J=8.1Hz,1H),7.76(t,J=7.2Hz,1H),7.34(t,J=7.2Hz,1H),6.22(d,J=3.8Hz,1H),5.88(d,J=5.2Hz,1H),5.75(d,J=8.1Hz,1H),5.34(d,J=5.8Hz,1H),4.73(d,J=2.1Hz,1H),4.57(m,1H),4.45(t,J=4.1Hz,1H),4.32(t,J=5.1Hz,1H),4.(t,J=5.1Hz,1H),3.91(t,J=4.5Hz,1H),3.36(s,3H)。
IR(KBr)νcm-1:3402,3342,2932,1687,1608,1586,1505,1460,1436,1385,1341,1274,1243,1111,1088,1060,1018。
实施例49(化合物编号1822)
Figure A0081465303561
使用2-甲氧苯胺51μL代替L-(-)-α-苯乙胺,与实施例(38-2)的化合物120mg,按照与实施例(38-3)同样进行合成,用高效液相色谱纯化(HPLC;Inertsil PREP-ODS 30×250mm),用25%乙腈水溶液洗脱,冷冻干燥得到目的化合物77mg。
1H NMR(CD3OD)δppm:8.15(d,J=9.0Hz,1H),7.89(d,J=8.2Hz,1H),7.13(m,1H),7.05(m,1H),6.95(m,1H),6.12(d,J=3.6Hz,1H),5.81(d,J=4.0Hz,1H),5.75(d,J=8.2Hz,1H),5.33(d,J=5.0Hz,1H),4.64(d,J=1.8Hz,1H),4.53(dd,J=2.0 and 5.4Hz,1H),4.44(t,J=4.0Hz,1H),4.23(t,J=4.5Hz,1H),4.06(m,1H),3.78(t,J=5.3Hz,1H),3.28(s,3H)。
IR(KBr)νcm-1:3401,3319,2975,2937,2840,1686,1603,1531,1486,1464,1437,1386,1332,1291,1254,1219,1203,1117,1060,1022。
实施例50(化合物编号1472)
Figure A0081465303562
使用4-(三氟甲基)苯胺57μL代替L-(-)-α-苯乙胺,与实施例(38-2)的化合物120mg,按照与实施例(38-3)同样进行合成,用高效液相色谱纯化(HPLC;Inertsil PREP-ODS 30×250mm),用32%乙腈水溶液洗脱,冷冻干燥得到目的化合物49mg。
1H NMR(CD3OD)δppm:7.89(d,J=8.7Hz,2H),7.86(d,J=8.1Hz,1H),7.64(d,J=8.7Hz,2H),6.12(m,1H),5.76(d,J=3.1Hz,1H),5.75(d,J=8.1Hz,1H),5.32(d,J=4.2Hz,1H),4.85(m,1H),4.52(dd,J=2.0and 6.2Hz,1H),4.46(m,1H),4.23(t,J=4.2Hz,1H),4.11(m,1H),3.73(dd,J=5.0 and 6.2Hz,1H),3.26(s,3H)。
IR(KBr)νcm-1:3401,3349,2936,1686,1617,1602,1532,1464,1412,1326,1266,1251,1163,1114,1066,1017。
实施例51(化合物编号1542)
Figure A0081465303571
使用2,4-二甲基苯胺56μL代替L-(-)-α-苯乙胺,与实施例(38-2)的化合物120mg,按照与实施例(38-3)同样进行合成,得到目的化合物118mg。
1H NMR(CD3OD)δppm:7.90(d,J=8.1Hz,2H),7.27(d,J=8.1Hz,1H),7.08(s,1H),7.01(d,J=8.1Hz,1H),6.07(m,1H),5.81(d,J=3.9Hz,1H),5.75(d,J=8.1Hz,1H),5.31(d,J=4.5Hz,1H),4.74(d,J=2.0Hz,1H),4.53(dd,J=1.8 and 5.7Hz,1H),4.44(t,J=4.3Hz,1H),4.28(t,J=4.4Hz,1H),4.18(m,1H),3.80(t,J=3.3Hz,1H),3.31(s,3H),2.30(s,3H),2.24(s,3H)。
IR(KBr)νcm-1:3408,3349,2925,2854,1685,1598,1525,1462,1395,1265,1205,1183,1135,1113,1061,1019。
实施例52(化合物编号4622)
Figure A0081465303581
使用3-氟-4-甲基苯胺52μL代替L-(-)-α-苯乙胺,与实施例(38-2)的化合物120mg,按照与实施例(38-3)同样进行合成,得到目的化合物104mg。
1H NMR(CD3OD)δppm:7.85(d,J=8.1Hz,2H),7.52(dd,J=2.0 and 11.8Hz,1H),7.30(dd,J=2.0 and 8.2Hz,1H),7.18(t,J=8.4Hz,1H),6.07(m,1H),5.77(d,J=3.6Hz,1H),5.75(d,J=8.1Hz,1H),5.29(d,J=4.2Hz,1H),4.85(m,1H),4.51(dd,J=1.8 and 6.1Hz,1H),4.44(m,1H),4.25(m,1H),4.08(m,1H),3.73(t,J=5.5Hz,1H),3.27(s,3H),2.23(s,3H)。
IR(KBr)νcm-1:3332,2927,2854,1685,1599,1530,1462,1414,1316,1268,1204,1119,1060,1020。
实施例53(化合物编号212)
使用4-正丙基苯胺81μL代替L-(-)-α-苯乙胺,与实施例(38-2)的化合物150mg,按照与实施例(38-3)同样进行合成,得到目的化合物93mg。
1H NMR(CD3OD)δppm:7.87(d,J=8.1Hz,2H),7.53(d,J=8.5Hz,2H),7.16(d,J=8.5Hz,2H),6.07(d,J=2.4Hz,1H),5.77(d,J=3.7Hz,1H),5.75(d,J=8.1Hz,1H),5.29(d,J=4.4Hz,1H),4.85(m,1H),4.52(dd,J=1.9 and 6.1Hz,1H),4.44(dd,J=3.3 and 4.2Hz,1H),4.25(dd,J=3.9 and 4.8Hz,1H),4.09(t,J=4.3Hz,1H),3.75(t,J=5.4Hz,1H),3.28(s,3H),2.57(t,J=7.8Hz,2H),1.64(m,2H),0.93(t,J=7.4Hz,3H)。
IR(KBr)νcm-1:3400,3351,2958,2932,2972,1685,1595,1527,1463,1413,1385,1320,1269,1112,1060,1018。
实施例54(化合物编号352)
Figure A0081465303591
使用4-正丁基苯胺81μL代替L-(-)-α-苯乙胺,与实施例(38-2)的化合物150mg,按照与实施例(38-3)同样进行合成,得到目的化合物38mg。
1H NMR(CD3OD)δppm:7.87(d,J=8.1Hz,1H),7.52(d,J=8.5Hz,2H),7.16(d,J=8.5Hz,2H),6.07(d,J=2.4Hz,1H),5.77(d,J=3.7Hz,1H),5.75(d,J=8.1Hz,1H),5.29(d,J=4.3Hz,1H),4.85(m,1H),4.52(dd,J=1.9 and 6.1Hz,1H),4.44(m,1H),4.25(t,J=4.2Hz,1H),4.09(t,J=4.4Hz,1H),3.74(t,J=5.5Hz,1H),3.28(s,3H),2.59(t,J=7.6Hz,2H),1.60(m,2H),1.35(m,2H),0.93(t,J=7.3Hz,3H)。
IR(KBr)νcm-1:3390,2957,2929,2873,2859,1685,1595,1527,1465,1413,1385,1353,1320,1259,1107,1060,1019。
实施例55(化合物编号562)
Figure A0081465303601
使用4-正戊基苯胺81μL代替4-叔丁基环己胺,按照与实施例(9-3)同样进行合成,得到目的化合物27mg。
1H NMR(CD3OD)δppm:7.87(d,J=8.1Hz,1H),7.52(d,J=8.6Hz,2H),7.15(d,J=8.6Hz,2H),6.07(d,J=2.5Hz,1H),5.77(d,J=3.7Hz,1H),5.75(d,J=8.1Hz,1H),5.29(d,J=4.3Hz,1H),4.85(m,1H),4.52(dd,J=2.0 and 6.0Hz,1H),4.44(t,J=3.9Hz,1H),4.25(t,J=4.2Hz,1H),4.09(m,1H),3.75(t,J=5.4Hz,1H),3.28(s,3H),2.59(t,J=7.7Hz,2H),1.60(m,2H),1.33(m,4H),0.90(t,J=6.9Hz,3H)。
IR(KBr)νcm-1:3323,2957,2930,2857,1687,1595,1526,1464,1413,1386,1320,1262,1111,1060,1018。
实施例56(化合物编号2662)
Figure A0081465303602
使用3,4-亚甲基二氧苯胺109mg代替4-叔丁基环己胺,按照与实施例(9-3)同样进行合成,得到目的化合物98mg。
1H NMR(CD3OD)δppm:7.86(d,J=8.1Hz,1H),7.26(d,J=2.1Hz,1H),7.03(dd,J=2.1 and 8.2Hz,1H),6.78(d,J=8.2Hz,1H),6.06(m,1H),5.94(s,1H),5.77(d,J=3.7Hz,1H),5.75(d,J=8.1Hz,1H),5.28(d,J=4.3Hz,1H),4.83(m,1H),4.52(dd,J=1.9 and 6.0Hz,1H),4.43(m,1H),4.25(m,1H),4.07(m,1H),3.73(t,J=5.5Hz,1H),3.29(s,3H)。
IR(KBr)νcm-1:3332,2925,2853,1685,1538,1503,1491,1462,1434,1385,1269,1245,1194,1139,1111,1060,1038,1020。
实施例57(化合物编号3712)
Figure A0081465303611
使用3,4-二氟苯胺75μL代替L-(-)-α-苯乙胺,与实施例(38-2)的化合物200mg,按照与实施例(38-3)同样进行合成,得到目的化合物20mg。
            1H NMR(CD3OD)δppm:7.85(d,J=8.1Hz,1H),7.76(m,1H),7.40(m,1H),7.23(quartet,J=9.5Hz,1H),6.09(m,1H),5.75(d,J=3.3Hz,1H),5.74(d,J=8.1Hz,1H),5.30(d,J=4.2Hz,1H),4.82(m,1H),4.50(dd,J=2.0 and 6.4Hz,1H),4.44(m,1H),4.25(dd,J=3.7and 4.7Hz,1H),4.10(m,1H),3.72(m,1H),3.26(s,3H)。
IR(KBr)νcm-1:3396,3334,2938,2837,1685,1618,1536,1518,1463,1414,1386,1327,1267,1242,12l0,1115,1060,1019。
实施例58(化合物编号982)
使用3-乙基苯胺75μL代替L-(-)-α-苯乙胺,与实施例(38-2)的化合物200mg,按照与实施例(38-3)同样进行合成,得到目的化合物111mg。
1H NMR(CD3OD)δppm:7.86(d,J=8.1Hz,1H),7.48(s,1H),7.47(d,J=8.0Hz,1H),7.24(dd,J=7.5 and 8.0Hz,1H),7.00(d,J=7.5Hz,1H),6.08(m,1H),5.77(d,J=3.7Hz,1H),5.75(d,J=8.1Hz,1H),5.30(d,J=4.4Hz,1H),4.84(m,1H),4.53(dd,J=1.9 and 6.1Hz,1H),4.44(m,1H),4.26(m,1H),4.08(m,1H),3.76(t,J=5.5Hz,1H),3.29(s,3H),2.64(quartet,J=7.6Hz,2H),1.23(t,J=7.6Hz,3H)。
IR(KBr)νcm-1:3410,2964,2930,1685,1611,1595,1542,1490,1462,1448,1422,1385,1330,1307,1266,1113,1059,1020。
实施例59(化合物编号5742)
Figure A0081465303621
使用3-氨基苯酚87μL代替4-叔丁基环己胺,按照与实施例(9-3)同样进行合成,得到目的化合物118mg。
1H NMR(CD3OD)δppm:7.87(d,J=8.1Hz,1H),7.23(t,J=2.1Hz,1H),7.13(t,J=8.1Hz,1H),7.03(dd,J=2.1 and 8.0Hz,1H),6.58(dd,J=2.1 and 8.0Hz,1H),6.07(m,1H),5.77(d,J=3.7Hz,1H),5.75(d,J=8.1Hz,1H),5.29(d,J=4.4Hz,1H),4.83(m,1H),4.52(dd,J=1.9 and6.0Hz,1H),4.44(m,1H),4.26(m,1H),4.08(m,1H),3.76(t,J=5.4Hz,1H),3.30(s,3H)。
IR(KBr)νcm-1:3390,2936,2836,1684,1604,1541,1494,1455,1386,1334,1271,1175,1113,1060,1020。
实施例60(化合物编号4132)
Figure A0081465303631
使用3-氯-4-氟苯胺116μL代替4-叔丁基环己胺,按照与实施例(9-3)同样进行合成,得到目的化合物27mg。
1H NMR(CD3OD)δppm:7.90(dd,J=2.7 and 6.6Hz,1H),7.85(d,J=8.1Hz,1H),7.15(m,2H),6.09(m,1H),5.76(d,J=3.0Hz,1H),5.75(d,J=8.1Hz,1H),5.30(d,J=3.9Hz,1H),4.83(m,1H),4.51(dd,J=2.0 and6.2Hz,1H),4.44(dd,J=3.2 and 4.2Hz,1H),4.26(m,1H),4.11(m,1H),3.73(m,1H),3.26(s,3H)。
IR(KBr)νcm-1:3409,2957,2928,2854,1685,1604,1537,1502,1466,1400,1385,1260,1138,1116,1065,1007。
实施例61(化合物编号1192)
Figure A0081465303632
使用2-正丙基苯胺135μL代替4-叔丁基环己胺,按照与实施例(9-3)同样进行合成,得到目的化合物44mg。
1H NMR(CD3OD)δppm:7.91(d,J=8.1Hz,1H),7.44(m,1H),7.27(m,1H),7.22(m,2H),6.09(m,1H),5.80(d,J=3.7Hz,1H),5.76(d,J=8.1Hz,1H),5.33(d,J=4.5Hz,1H),4.72(d,J=2.0Hz,1H),4.52(dd,J=2.0and 5.7Hz,1H),4.45(m,1H),4.29(t,J=4.5Hz,1H),4.10(t,J=4.3Hz,1H),3.80(t,J=5.3Hz,1H),3.34(s,3H),2.61(t,J=7.2Hz,2H),1.63(m,2H),0.95(t,J=7.3Hz,3H)。
IR(KBr)νcm-1:3423,2960,2933,2873,1685,1588,1525,1455,1385,1267,1111,1060,1019。
实施例62(化合物编号2242)
Figure A0081465303641
使用4-正丁氧苯胺95μL代替4-叔丁基环己胺,按照与实施例(9-3)同样进行合成,得到目的化合物47mg。
1H NMR(CD3OD)δppm:7.87(d,J=8.1Hz,1H),7.51(d,J=8.9Hz,2H),6.89(d,J=8.9Hz,2H),6.06(m,1H),5.77(d,J=3.7Hz,1H),5.75(d,J=8.1Hz,1H),5.29(d,J=4.4Hz,1H),4.83(d,J=2.1Hz,1H),4.52(dd,J=2.0 and 5.9Hz,1H),4.44(dd,J=3.3 and 4.2Hz,1H),4.25(m,1H),4.08(t,J=4.4Hz,1H),3.96(t,J=6.5Hz,2H),3.74(t,J=5.4Hz,1H),3.29(s,3H),1.74(m,2H),1.50(m,2H),0.98(t,J=7.6Hz,3H)。
IR(KBr)νcm-1:3407,3358,2958,2935,2874,1685,1597,1528,1512,1465,1414,1385,1245,1173,1112,1061。
实施例63(化合物编号2382)
使用4-正己氧苯胺110mg代替4-叔丁基环己胺,按照与实施例(9-3)同样进行合成,得到目的化合物46mg。
1H NMR(CD3OD)δppm:7.86(d,J=8.1Hz,1H),7.50(m,2H),6.89(m,2H),6.06(m,1H),5.77(d,J=3.7Hz,1H),5.75(d,J=8.1Hz,1H),5.28(d,J=4.2Hz,1H),4.83(d,J=1.7Hz,1H),4.52(dd,J=2.1 and 5.9Hz,1H),4.44(t,J=4.3Hz,1H),4.25(m,1H),4.08(m,1H),3.96(t,J=6.5Hz,2H),3.74(t,J=5.4Hz,1H),3.29(s,3H),1.75(m,2H),1.48(m,2H),1.37(m,4H),0.98(t,J=7.1Hz,3H)。
IR(KBr)νcm-1:3348,2933,2871,1685,1597,1528,1513,1467,1414,1385,1245,1111,1078,1060,1019。
实施例64(化合物编号2312)
Figure A0081465303652
使用4-正戊氧苯胺105μL代替4-叔丁基环己胺,按照与实施例(9-3)同样进行合成,得到目的化合物105mg。
1H NMR(CD3OD)δppm:7.86(d,J=8.1Hz,1H),7.51(m,2H),6.89(m,2H),6.07(m,1H),5.77(d,J=3.8Hz,1H),5.75(d,J=8.1Hz,1H),5.29(d,J=4.3Hz,1H),4.83(d,J=2.0Hz,1H),4.52(dd,J=1.9 and 5.9Hz,1H),4.44(m,1H),4.25(m,1H),4.09(t,J=4.3Hz,1H),3.96(t,J=6.3Hz,2H),3.74(t,J=5.4Hz,1H),3.29(s,3H),1.76(m,2H),1.44(m,2H),0.95(t,J=7.2Hz,3H)。
IR(KBr)νcm-1:3407,2956,2934,2872,1685,1597,1528,1513,1466,1414,1386,1247,1112,1060,1019。
实施例65(化合物编号4202)
Figure A0081465303661
使用3-三氟甲基-4-氟苯胺73μL代替4-叔丁基环己胺,按照与实施例(9-3)同样进行合成,得到目的化合物114mg。
1H NMR(CD3OD)δppm:8.09(dd,J=2.6 and 6.3Hz,1H),7.97(m,1H),7.86(d,J=8.1Hz,1H),7.33(t,J=9.6Hz,1H),6.11(m,1H),5.75(m,2H),5.31(d,J=3.8Hz,1H),4.82(d,J=2.1Hz,1H),4.51(dd,J=2.0 and6.3Hz,1H),4.45(dd,J=3.2 and 4.3Hz,1H),4.26(t,J=4.0Hz,1H),4.12(m,1H),3.72(t,J=5.5Hz,1H),3.25(s,3H)。
IR(KBr)νcm-1:3407,2932,1686,1542,1508,1464,1429,1386,1329,1269,1243,1136,1056,1019。
实施例66(化合物编号6596)
Figure A0081465303662
使用2-氨基噻唑45mg代替L-(-)-α-苯乙胺,与实施例(38-2)的化合物120mg,按照与实施例(38-3)同样进行合成,得到目的化合物81mg。
           1H NMR(CD3OD)δppm:7.84(d,J=8.1Hz,1H),7.50(d,J=3.6Hz,1H),7.18(d,J=3.6Hz,1H),6.19(m,1H),5.76(d,J=3.9Hz,1H),5.74(d,J=8.1Hz,1H),5.32(d,J=4.4Hz,1H),4.83(m,1H),4.50(dd,J=2.3 and 5.8Hz,1H),4.45(m,1H),4.27(m,1H),4.08(m,1H),3.75(t,J=5.3Hz,1H),3.27(s,3H)。
IR(KBr)νcm-1:3334,2937,2834,1685,1541,1463,1393,l322,1269,1224,1138,1113,1059,1019。
实施例67(化合物编号6601)
Figure A0081465303671
使用2-氨基-4,5-二氢噻唑45mg代替L-(-)-α-苯乙胺,与实施例(38-2)的化合物120mg,按照与实施例(38-3)同样进行合成,得到目的化合物54mg。
1H NMR(CD3OD)δppm:7.87(d,J=8.1Hz,1H),6.24(d,J=3.5Hz,1H),5.84(d,J=4.9Hz,1H),5.74(d,J=8.1Hz,1H),5.16(d,J=5.1Hz,1H),4.67(d,J=2.1Hz,1H),4.51(dd,J=2.1 and 4.8Hz,1H),4.38(t,J=4.1Hz,1H),4.24(t,J=4.9Hz,1H),3.97(t,J=4.8Hz,1H),3.86(t,J=4.9Hz,1H),3.78(t,J=7.9Hz,2H),3.41(s,3H),3.34(m,2H)。
IR(KBr)νcm-1:3313,2939,1685,1614,1549,1465,1442,1395,1333,1266,1224,1204,1113,1058,1018。
实施例68(化合物编号6606)
Figure A0081465303681
使用2-氨基-5-环丙基-1,3,4-噻二唑42mg代替L-(-)-α-苯乙胺,与实施例(38-2)的化合物80mg,按照与实施例(38-3)同样进行合成,得到目的化合物59mg。
1H NMR(CD3OD)δppm:7.84(d,J=8.1Hz,1H),6.19(d,J=2.4Hz,1H),5.76(d,J=3.9Hz,1H),5.73(d,J=8.1Hz,1H),5.32(d,J=4.2Hz,1H),4.83(d,J=2.2Hz,1H),4.50(dd,J=2.2 and 5.8Hz,1H),4.45(dd,J=2.3 and 4.2Hz,1H),4.24(m,1H),4.10(m,1H),3.73(t,J=5.4Hz,1H),3.27(s,3H),2.47(m,1H),1.22(m,2H),1.06(m,2H)。
IR(KBr)νcm-1:3333,2935,2853,1685,1536,1483,1464,1393,1308,1273,1204,1137,1115,1058,1017。
实施例69(化合物编号6611)
Figure A0081465303682
使用2-氨基喹啉42mg代替L-(-)-α-苯乙胺,与实施例(38-2)的化合物120mg,按照与实施例(38-3)同样进行合成,得到目的化合物56mg。
1H NMR(CD3OD)δppm:9.07(d,J=2.2Hz,1H),8.77(d,J=2.5Hz,1H),7.87(d,J=8.1Hz,1H),7.67(m,4H),6.18(m,1H),5.76(m,2H),5.36(d,J=3.8Hz,1H),4.87(m,1H),4.54(dd,J=2.0 and 6.1Hz,1H),4.49(dd,J=2.1 and 4.2Hz,1H),4.27(dd,J=3.6 and 4.9Hz,1H),4.15(m,1H),3.76(dd,J=5.1 and 6.2Hz,1H),3.27(s,3H)。
实施例70(化合物编号6616)
使用ホロチン盐酸盐153mg和三乙胺204μL代替4-叔丁基环己胺,按照与实施例(9-3)同样进行合成,得到目的化合物81mg。
1H NMR(CD3OD)δppm:7.88(d,J=8.1Hz,1H),7.19(s,1H),6.08(d,J=3.6Hz,1H),5.82(d,J=4.4Hz,1H),5.74(d,J=8.1Hz,1H),5.28(d,J=5.0Hz,1H),4.79(d,J=2.1Hz,1H),4.54(dd,J=2.2 and 5.1Hz,1H),4.43(t,J=4.0Hz,1H),4.28(m,1H),4.05(m,1H),3.79(t,J=5.0Hz,1H),3.41(s,3H)。
IR(KBr)νcm-1:3379,3071,2936,2834,1683,1520,1462,1385,1316,1268,1190,1110,1060,1018。
实施例71(化合物编号6621)
使用吡咯烷82μL,按照与实施例3同样进行合成,得到目的化合物12mg。
1H NMR(CD3OD)δppm:7.95(d,J=8.1Hz,1H),5.85(d,J=4.0Hz,1H),5.75(d,J=8.1Hz,1H),5.56(d,J=4.4Hz,1H),5.15(d,J=6.6Hz,1H),4.55(m,2H),4.33(t,J=4.4Hz,1H),4.28(t,J=4.6Hz,1H),3.90(m,2H),3.68(m,2H),3.45(m,2H),3.42(s,3H),1.93(m,4H)。
IR(KBr)νcm-1:3389,2935,2883,1687,1614,1515,1455,1389,1338,1268,1196,1136,1114,1091,1060。
实施例72(化合物编号66)
Figure A0081465303701
使用N-甲基苯胺32μL代替L-(-)-α-苯乙胺,与实施例(38-2)的化合物80mg,按照与实施例(38-3)同样进行合成,得到目的化合物40mg。
1H NMR(CD3OD)δppm:7.88(d,J=8.1Hz,1H),7.45-7.05(m,5H),5.87(d,J=5.2Hz,1H),5.69(d,J=8.1Hz,1H),5.66(d,J=5.2Hz,1H),4.85(m,1H),4.40(m,1H),4.23(m,2H),3.18(m,1H),3.13(m,1H),3.55(s,3H),3.36(s,3H)。
IR(KBr)νcm-1:3335,2935,2833,1685,1593,1496,1463,1390,1271,1203,1134,1089,1060。
实施例73(化合物编号6626)
使用N-甲基正丁胺300μL代替L-(-)-α-苯乙胺,与实施例(38-2)的化合物160mg,按照与实施例(38-3)同样进行合成,得到目的化合物61mg。
1H NMR(CD3OD)δppm:7.95(d,J=8.1Hz,1H),5.88(m,1H),5.74(d,J=8.1Hz,1H),5.27(dd,J=4.3 and 18.0Hz,1H),5.15(m,1H),4.52(m,2H),4.31(t,J=4.4Hz,1H),4.29(br s,1H),3.91(m,2H),3.44 and 3.42(2s,3H),3.10 and 2.92(2s,3H),1.58(m,2H),1.32(m,2H),0.94(t,J=7.3Hz,3H)。
IR(KBr)νcm-1:3403,2958,2933,2874,1686,1625,1492,1463,1408,1386,1268,1111,1091,1061,1024。
实施例74(化合物编号6627)
Figure A0081465303711
使用3-苯基丙胺200μL,按照与实施例3同样进行合成,得到目的化合物30mg。
1H NMR(CD3OD)δppm:7.87(d,J=8.1Hz,1H),7.28-7.14(m,5H),5.95(m,1H),5.79(d,J=4.2Hz,1H),5.75(d,J=8.1Hz,1H),5.21(d,J=4.4Hz,1H),4.68(d,J=2.0Hz,1H),4.49(m,1H),4.38(m,1H),4.23(t,J=4.5Hz,1H),4.03(m,1H),3.70(t,J=5.2Hz,1H),3.34(s,3H),3.32(m,2H),2.65(t,J=7.5Hz,2H)。
IR(KBr)νcm-1:3350,2935,1685,1532,1496,1462,1391,1267,1136,1116,1094,1058。
实施例75(化合物编号6628)
Figure A0081465303721
使用3,3-二苯基丙胺200μL,按照与实施例3同样进行合成,得到目的化合物36mg。
1H NMR(CD3OD)δppm:7.86(d,J=8.1Hz,1H),7.30-7.12(m,10H),5.93(m,1H),5.79(d,J=4.0Hz,1H),5.75(d,J=8.1Hz,1H),5.19(d,J=4.4Hz,1H),4.67(d,J=2.1Hz,1H),4.49(m,1H),4.37(m,1H),4.23(t,J=4.5Hz,1H),4.00(m,2H),3.68(t,J=5.2Hz,1H),3.30(s,3H),3.35-3.17(m,2H),2.32(quartet,J=7.7Hz,2H)。
IR(KBr)νcm-1:3344,3061,3027,2936,1685,1529,1495,1453,1390,1268,1136,1115,1095,1057,1030。
实施例76(化合物编号69)
使用苯酚160mg代替4-叔丁基环己胺,按照与实施例(9-3)同样进行合成,得到目的化合物14mg。
1H NMR(CD3OD)δppm:7.93(d,J=8.1Hz,1H),7.42(m,2H),7.28(m,1H),7.14(m,2H),6.34(d,J=4.0Hz,1H),5.85(d,J=4.4Hz,1h),5.75(d,J=8.1Hz,1H),5.23(d,J=5.8Hz,1H),4.62(d,J=1.6Hz,1H),4.57(m,1H),4.45(t,J=4.3Hz,1H),4.27(t,J=4.7Hz,1H),4.00(m,2H),3.42(s,3H)。
IR(KBr)νcm-1:3404,2925,2852,1684,1591,1487,1460,1386,1301,1248,1195,1162,1111,1064,1019。
实施例77(化合物编号6629)
Figure A0081465303731
使用苯乙醇191μL代替4-叔丁基环己胺,按照与实施例(9-3)同样进行合成,得到目的化合物38mg。
1H NMR(CD3OD)δppm:7.89(d,J=8.1Hz,1H),7.25(m,5H),6.07(d,J=4.0Hz,1H),5.83(d,J=4.6Hz,1H),5.72(d,J=8.1Hz,1H),5.12(d,J=5.8Hz,1H),4.55(m,2H),4.39(t,J=6.8Hz,2H),4.35(t,J=4.2Hz,1H),4.21(t,J=4.7Hz,1H),3.92(m,1H),3.86(t,J=4.9Hz,1H),3.37(s,3H),2.98(t,J=6.8Hz,2H)。
IR(KBr)νcm-1:3420,2934,1684,1462,1389,1265,1113,1088,1062,1026。
实施例78(化合物编号6630)
使用环己醇169μL代替4-叔丁基环己胺,按照与实施例(9-3)同样进行合成,得到目的化合物33mg。
1H NMR(CD3OD)δppm:7.91(d,J=8.1Hz,1H),6.10(d,J=4.0Hz,1H),5.85(d,J=4.6Hz,1H),5.73(d,J=8.1Hz,1H),5.14(d,J=5.8Hz,1H),4.56(m,2H),4.36(t,J=4.3Hz,1H),4.24(t,J=5.0Hz,1H),3.92(m,2H),3.46(s,3H),1.88(m,2H),1.75(m,2H),1.60-1.30(m,6H)。
实施例79(化合物编号6631)
Figure A0081465303741
将实施例(38-2)的化合物2g溶于DMF30mL中,加入苯胺1.04mL和HOBT 820mg和DIPC1.37mL,在室温搅拌。1小时后,加入甲醇1mL,减压蒸除溶剂。残渣用硅胶柱(80g)纯化,用3%甲醇-二氯甲烷洗脱,得到目的化合物1.5g。
1H NMR(CD3OD)δppm:7.87(d,J=8.1Hz,1H),7.65(m,2H),7.35(m,2H),7.16(t,J=7.3Hz,1H),6.23(d,J=3.8Hz,1H),5.80(d,J=3.7Hz,1H),5.72(d,J=8.1Hz,1H),5.20(d,J=5.0Hz,1H),4.78(dd,J=3.8 and 5.9Hz,1H),4.56(dd,J=1.8 and 6.1Hz,1H),4.38(t,J=5.6Hz,1H),4.29(m,1H),3.84(t,J=5.5Hz,1H),3.30(s,3H),1.88(m,4H),1.72(m,4H)。
IR(KBr)νcm-1:3331,3100,3064,2959,2940,1690,1599,1533,1498,1445,1388,1321,1300,1268,1243,1207,1101,1072。
(79-2)
Figure A0081465303751
将实施例(79-1)的化合物150mg溶于4.5mL吡啶中,加入正庚酸酐131μL和二甲基氨基吡啶3mg,在室温搅拌。4小时后,加入甲醇1mL,减压蒸除溶剂。残渣溶于乙酸乙酯150mL,依次用各150mL的饱和碳酸氢钠水溶液和饱和氯化钠水溶液洗净,用无水硫酸钠干燥。减压蒸除溶剂,残渣用硅胶柱(8g)纯化,用1.5%的甲醇-二氯甲烷洗脱,得到目的化合物155mg。
1H NMR(CD3OD)δppm:7.84(d,J=8.1Hz,1H),7.63(d,J=7.5Hz,2H),7.34(t,J=8.0Hz,2H),7.16(t,J=7.3Hz,1H),6.22(d,J=3.8Hz,1H),5.94(d,J=4.7Hz,1H),5.74(d,J=8.1Hz,1H),5.38(t,J=4.7Hz,1H),5.22(d,J=5.0Hz,1H),4.85(m,2H),4.55(m,1H),4.39(t,J=5.5Hz,1H),4.09(t,J=5.0Hz,1H),3.30(s,3H),2.38(t,J=7.2Hz,2H),1.88(m,4H),1.72(m,4H),1.60(m,2H),1.30(m,6H),0.88(t,J=6.8Hz,3H)。
(79-3)
Figure A0081465303752
将实施例(79-2)的化合物155mg溶于二氯甲烷73mL中,加入三氟乙酸3mL,在室温搅拌。4小时后,减压蒸除溶剂,将残渣用乙醇共沸数次。残渣用硅胶柱(8g)纯化,用6%甲醇-二氯甲烷洗脱,得到目的化合物121mg。
1H NMR(CD3OD)δppm:7.86(d,J=8.1Hz,1H),7.64(m,2H),7.35(m,2H),7.15(t,J=7.4Hz,1H),6.08(d,J=2.5Hz,1H),5.90(d,J=4.4Hz,1H),5.76(d,J=8.1Hz,1H),5.37(t,J=4.7Hz,1H),5.31(d,J=4.5Hz,1H),4.85(m,1H),4.50(m,2H),4.10(m,1H),4.02(t,J=5.2Hz,1H),3.26(s,3H),2.36(t,J=7.3Hz,2H),1.60(m,2H),1.30(m,6H),0.87(t,J=6.8Hz,3H)。
IR(KBr)νcm-1:3342,3100,3065,2958,2931,2957,1689,1599,1534,1498,1462,1444,1384,1322,1263,1238,1206,1158,1109,1060,1021。
实施例80(化合物编号5)
Figure A0081465303761
将实施例(79-1)的化合物150mg溶于4.5mL吡啶中,加入壬酸酐180μL和二甲基氨基吡啶8mg,在室温搅拌。1小时后,减压蒸除溶剂。残渣溶于乙酸乙酯100mL,依次用各100mL的饱和碳酸氢钠水溶液和饱和氯化钠水溶液洗净,用无水硫酸钠干燥。减压蒸除溶剂,残渣溶于二氯甲烷77mL中,加入三氟乙酸3.85mL,在室温搅拌。1.5小时后减压蒸除溶剂,用甲苯共沸数次后,残渣用硅胶柱(25g)纯化,用10%的甲醇-二氯甲烷洗脱,得到目的化合物41mg。
1H NMR(CD3OD)δppm:7.86(d,J=8.1Hz,1H),7.64(m,2H),7.34(m,2H),7.15(m,1H),6.09(m,1H),5.90(d,J=4.4Hz,1H),5.76(d,J=8.1Hz,1H),5.37(t,J=4.7Hz,1H),5.31(d,J=4.6Hz,1H),4.85(m,1H),4.50(m,2H),4.10(m,1H),4.02(t,J=5.2Hz,1H),3.26(s,3H),2.36(t,J=7.3Hz,2H),1.58(m,2H),1.28(m,10H),0.88(t,J=6.8Hz,3H)。
IR(KBr)νcm-1:3357,3100,3063,2955,2927,2855,1687,1600,1535,1498,1465,1444,1385,1322,1270,1243,1154,1113,1060,1021。
实施例81(化合物编号6)
Figure A0081465303771
使用正癸酸酐代替壬酸酐,按照与实施例80同样进行合成,得到目的化合物120mg。
1H NMR(CD3OD)δppm:7.86(d,J=8.1Hz,1H),7.63(m,2H),7.33(t,J=7.8Hz,2H),7.14(t,J=7.4Hz,1H),6.08(d,J=4.0Hz,1H),5.90(d,J=4.3Hz,1H),5.76(d,J=8.1Hz,1H),5.37(t,J=4.7Hz,1H),5.31(d,J=4.5Hz,1H),4.85(m,1H),4.50(m,2H),4.09(t,J=4.3Hz,1H),4.02(t,J=5.2Hz,1H),3.26(s,3H),2.36(t,J=7.3Hz,2H),1.60(m,2H),1.27(m,12H),0.89(t,J=6.8Hz,3H)。
IR(KBr)νcm-1:3343,3-98,3064,2955,2927,2854,1690,1599,1534,1498,1463,1444,1383,1321,1266,1243,1152,1112,1060,1021。
实施例82(化合物编号7)
使用正十二烷酸酐代替壬酸酐,按照与实施例80同样进行合成,得到目的化合物79mg。
1H NMR(CD3OD)δppm:7.86(d,J=8.1Hz,1H),7.64(m,2H),7.33(m,2H),7.14(m,1H),6.08(d,J=4.0Hz,1H),5.90(d,J=4.4Hz,1H),5.76(d,J=8.1Hz,1H),5.37(t,J=4.7Hz,1H),5.31(d,J=4.5Hz,1H),4.85(m,1H),4.50(m,2H),4.09(m,1H),4.02(t,J=5.2Hz,1H),3.26(s,3H),2.36(t,J=7.3Hz,2H),1.60(m,2H),1.27(m,16H),0.89(t,J=7.4Hz,3H)。
IR(KBr)νcm-1:3343,3098,3064,2926,2854,1689,1600,1534,1498,1464,1444,1384,1322,1269,1243,1149,1113,1060,1021。
实施例83(化合物编号9)
Figure A0081465303782
使用棕榈酸酐465mg代替壬酸酐,与实施例(79-1)的化合物270mg,按照与实施例80同样进行合成,得到目的化合物297mg。
1H NMR(CD3OD)δppm:7.86(d,J=8.1Hz,1H),7.63(m,2H),7.34(m,2H),7.14(m,1H),6.08(d,J=2.5Hz,1H),5.90(d,J=4.4Hz,1H),5.76(d,J=8.1Hz,1H),5.37(t,J=4.7Hz,1H),5.31(d,J=4.6Hz,1H),4.85(m,1H),4.50(m,2H),4.10(m,1H),4.02(t,J=5.2Hz,1H),3.26(s,3H),2.36(t,J=7.3Hz,2H),1.60(m,2H),1.27(m,24H),0.89(t,J=6.8Hz,3H)。
IR(KBr)νcm-1:3346,3099,3064,2925,2853,1691,1599,1534,1498,1464,1444,1412,1382,1320,1268,1242,1148,1113,1086,1060,1021。
实施例84(化合物编号567)
Figure A0081465303791
将实施例(9-2)的化合物700mg溶于二甲基甲酰胺9mL中,加入4-戊基苯胺497μL和HOBT 303mg和二异丙基碳化二亚胺504μL,在室温搅拌。105分钟后,减压蒸除溶剂,残渣溶于乙酸乙酯200ml,依次用各200mL的0.01N盐酸水溶液、饱和碳酸氢钠水溶液、饱和氯化钠水溶液洗净,用无水硫酸钠干燥。减压蒸除溶剂,残渣用硅胶柱(103g)色谱纯化,用4%甲醇-二氯甲烷洗脱,得到目的化合物764mg。
1H NMR(CDCl3)δppm:9.06(br s,1H),8.40(s,1H),7.70(d,J=8.8Hz,1H),7.49(d,J=8.1Hz,2H),7.14(d,J=8.1Hz,2H),7.10(br s,1H),6.48(d,J=4.4Hz,1H),6.10(br s,1H),5.79(d,J=2.9Hz,1H),5.73(d,J=8.1Hz,1H),4.80(dd,J=4.4 and 5.9Hz,1H),4.75(m,2H),4.42(m,1H),4.12(t,J=6.6Hz,1H),4.03(m,1H),3.60(br s,1H),3.42(s,3H),2.56(t,J=7.3Hz,2H),1.58(m,2H),1.49(s,3H),1.45(s,3H),1.35(m,4H),0.88(t,J=6.8Hz,3H)。
(84-2)
Figure A0081465303801
将实施例(84-1)化合物760mg溶于25mL吡啶中,加入十二酸酐677mg和二甲基氨基吡啶15mg,在室温搅拌。2小时40分钟后,减压蒸除溶剂,残渣溶于二氯甲烷200mL,依次用各200mL的0.01N盐酸水溶液、饱和碳酸氢钠水溶液和饱和氯化钠水溶液洗净,用无水硫酸钠干燥。减压蒸除溶剂,残渣溶于甲醇50mL中,加入700mg大网树脂15,加热回流。6小时后,用硅藻土过滤,减压蒸除溶剂,残渣用硅胶柱(104g)纯化,用7%的甲醇-二氯甲烷洗脱,得到目的化合物665mg。
1H NMR(CD3OD)δppm:7.86(d,J=8.1Hz,1H),7.51(d,J=8.5Hz,2H),7.15(d,J=8.5Hz,2H),6.07(d,J=3.8Hz,1H),5.91(d,J=4.5Hz,1H),5.76(d,J=8.1Hz,1H),5.36(t,J=4.7Hz,1H),5.30(d,J=4.6Hz,1H),4.85(m,1H),4.52(dd,J=1.6 and 5.1Hz,1H),4.48(t,J=3.9Hz,1H),4.08(m,1H),4.03(t,J=5.1Hz,1H),3.27(s,3H),2.59(t,J=7.7Hz,2H),2.36(t,J=7.3Hz,2H),1.60(m,4H),1.40-1.25(m,20H),0.90(m,6H)。
IR(KBr)νcm-1:3344,2956,2926,2854,1690,1595,1527,1464,1413,1381,1319,1269,1242,1150,1112,1060,1021。
实施例85(化合物编号20)
将实施例43的化合物300mg溶于3mL吡啶中,加入乙酸酐0.15mL和二甲基氨基吡啶4mg,在室温搅拌。1小时后,减压蒸除溶剂,残渣溶于乙酸乙酯50mL,用饱和碳酸氢钠水溶液50mL洗涤2次后,用无水硫酸钠干燥。减压蒸除溶剂,残渣硅胶柱(8g)纯化,用3%的甲醇-二氯甲烷洗脱,得到目的化合物270mg。
1H NMR(CD3OD)δppm:7.71(d,J=8.1Hz,1H),7.64(d,J=8.5Hz,2H),7.35(t,J=8.0Hz,2H),7.16(t,J=7.3Hz,1H),6.09(t,J=1.9Hz,1H),5.89(d,J=8.1Hz,1H),5.84(d,J=3.6Hz,1H),5.80(m,1H),5.70(m,1H),5.51(d,J=2.7Hz,1H),5.34(dd,J=3.7 and 5.1Hz,1H),4.85(m,1H),4.41(dd,J=2.0 and 6.5Hz,1H),3.91(dd,J=5.4 and 6.3Hz,1H),3.19(s,3H),2.11(s,3H),2.08(s,6H)。
IR(KBr)νcm-1:3342,3098,3064,2935,2850,1750,1693,1600,1534,1498,1445,1375,1322,1238,1114,1053。
实施例86(化合物编号163)
将实施例(9-1)的化合物206mg和1,8-二氮杂双环[5.4.0]-7-十一烯(DBU)120μL溶于二甲基甲酰胺(DMF)4mL中,加入4-甲氧苄基氯甲基醚(T.Benneche,P.Strande K.Undeheim,合成杂志,第9卷,762-763页,1983年)130mg,在室温搅拌。2.5小时后,减压蒸除溶剂,残渣溶于二氯甲烷100mL,依次用各100mL的0.01N盐酸水溶液和饱和碳酸氢钠水溶液洗净,用无水硫酸镁干燥。减压蒸除溶剂,残渣硅胶柱(30g)纯化,用1.5%的甲醇-二氯甲烷洗脱,得到目的化合物224mg。
1H MMR(CDCl3)δppm:7.67(d,J=8.1Hz,1H),7.31(d,J=8.8Hz,2H),7.12(br s,1H),6.85(m,2H),6.40(d,4.4Hz,1H),5.95(d,J=4.4Hz,1H),5.75(d,J=8.1Hz,1H),5.59(br s,1H),5.44(dd,J=9.5 and 16.1Hz,2H),4.73(m,2H),4.62(s,2H),4.56(d,J=8.1 Hz,1H),4.52(d,J=1.5Hz,1H),4.25(m,1H),4.13(t,J=5.1Hz,1H),4.02(dd,J=5.9 and8.1Hz,1H),3.82(s,3H),3.79(s,3H),3.59(s,3H),3.02(d,J=6.6Hz,1H),1.50(s,3H),1.45(s,3H)。
IR(KBr)νcm-1:3449,3362,3104,2988,2934,2853,1715,1669,1612,1514,1457,1412,1371,1304,1280,1248,1219,1167,1086,1065,1015。
(86-2)
Figure A0081465303831
将实施例(86-1)的化合物224mg溶于DMF2mL中,在氮气流下0℃搅拌,加入氢化钠(60%)20mg和1-碘己烷497μL。5分钟后升温至室温,再保留35分钟后减压蒸除溶剂。残渣溶于100mL二氯甲烷,分别用各100mL的0.01N盐酸水溶液和饱和碳酸氢钠水溶液洗净,用无水硫酸镁干燥。减压蒸除溶剂,残渣用硅胶柱(40g)纯化,用1%甲醇-二氯甲烷洗脱,得到目的化合物64mg。
1H NMR(CDCl3)δppm:7.92(d,J=8.1Hz,1H),7.31(d,J=8.8Hz,2H),7.19(br s,1H),6.86(d,J=8.8Hz,2H),6.39(d,J=4.4Hz,1H),5.88(d,J=1.5Hz,1H),5.72(d,J=8.1Hz,1H),5.68(br s,1H),5.43(dd,J=10.3 and 17.5Hz,2H),4.75(m,2H),4.63(s,2H),4.60(d,J=8.1Hz,1H),4.55(d,J=1.5Hz,1H),4.00(m,2H),3.95(m,1H),3.83(m,1H),3.81(s,3H),3.79(s,3H),3.65(m,1H),3.50(s,3H),1.62(m,2H),1.50(s,3H),1.46(s,3H),1.40-1.22(m,6H),0.88(m,3H)。
IR(KBr)νcm-1:3450,3342,3103,2932,2858,1713,1699,1670,1612,1514,1456,1411,1371,1304,1278,1248,1220,1167,1092,1067,1017。
(86-3)
Figure A0081465303841
将实施例(86-2)的化合物64mg溶于二氯甲烷1mL中,加入水50μL和2,3-二氯-5,6-二氰基-1,4-苯醌98mg,在室温搅拌。4小时后,滤除不溶物,用二氯甲烷100mL稀释,分别用各100mL的饱和碳酸氢钠水溶液和饱和氯化钠水溶液洗净,用无水硫酸镁干燥。减压蒸除溶剂,残渣用硅胶柱(10g)纯化,用3%甲醇-二氯甲烷洗脱,得到目的化合物40mg。
1H NMR(CDCl3)δppm:8.33(br s,1H),7.92(d,J=8.1Hz,1H),7.19(brs,1H),6.39(d,J=4.4Hz,1H),5.91(d,J=2.2Hz,1H),5.77(br s,1H),5.71(d,J=8.1Hz,1H),4.75(dd,J=4.4 and 6.6Hz,2H),4.59(d,J=8.1Hz,1H),4.54(d,J=1.5Hz,1H),4.00(m,3H),3.81(s,3H),3.75(m,1H),3.60(m,1H),3.51(s,3H),1.60(m,2H),1.50(s,3H),1.46(s,3H),1.40-1.22(m,6H),0.88(t,J=6.6Hz,3H)。
IR(KBr)νcm-1:3454,3199,3098,3063,2988,2934,2859,1696,1458,1383,1307,1265,1248,1220,1166,1122,1092,1066,1016。(86-4)
Figure A0081465303842
将实施例(86-3)的化合物40mg溶于甲醇6mL和水3mL的混合溶剂中,加入1N氢氧化钠水溶液334μL,在室温搅拌。8分钟后,加入ダゥエックス50W×8(H+型)10mL柱,用甲醇-水(1∶1)100mL洗脱。减压蒸除溶剂,残渣与甲苯共沸,干燥,溶于DMF0.6mL中,加入1-羟基苯并三唑14mg和二异丙基碳化二亚胺24μL和4-乙基苯胺0.6mL,在室温搅拌。2小时后减压蒸除溶剂,将残渣溶于二氯甲烷100mL,用各100mL的0.01N盐酸水溶液和饱和碳酸氢钠水溶液洗涤后,用无水硫酸镁干燥。减压蒸除溶剂后,将残渣溶于甲醇2mL,加入60mg的大网树脂15,加热回流。7小时后,滤除不溶物,通过分取(分取)硅胶薄层色谱法,用二氯甲烷-甲醇(12∶1)展开纯化,得到目的化合物30mg。
1H NMR(CD3OD)δppm:7.88(d,J=8.1Hz,1H),7.54(d,J=8.5Hz,2H),7.18(d,J=8.5Hz,2H),6.06(d,J=2.5Hz,1H),5.84(d,J=3.4Hz,1H),5.76(d,J=8.1Hz,1H),5.30(d,J=4.2Hz,1H),4.84(m,1H),4.54(m,1H),4.45(m,1H),4.11(t,J=4.4Hz,1H),4.00(m,1H),3.77(m,1H),3.68(m,1H),3.55(m,1H),3.24(s,3H),2.62(quartet,J=7.6Hz,2H),1.55(m,2H),1.40-1.20(m,6H),1.22(t,J=7.6Hz,3H),0.87(m,3H)。
IR(KBr)νcm-1:3333,2960,2932,2872,2860,1686,1595,1527,1464,1413,1386,1319,1268,1102,1060,1019。
实施例87(化合物编号5042)
Figure A0081465303851
(87-1)
将1H,1H-七氟丁醇1.2mL溶于四氢呋喃10mL,加入氢氧化钠400mg和4-氟硝基苯1.27mL,在室温搅拌。4小时后,加入乙酸乙酯100mL,用各100mL的水和饱和氯化钠水溶液洗净,用无水硫酸镁干燥。减压蒸除溶剂,残渣用硅胶柱(150g)纯化,用己烷-乙酸乙酯(30∶1)洗脱,得到1H,1H-七氟丁基-4-硝基苯基醚2.0189g。
1H NMR(CDCl3)δppm:8.26(d,J=9.1Hz,2H),7.05(d,J=9.1Hz,2H),4.56(t,J=12.4Hz,2H)。
(87-2)
将实施例(87-1)的化合物2g溶于甲醇16mL和四氢呋喃4mL的混合溶剂中,将所得溶液加入到溶有肼1水合物3.12g的甲醇20mL溶液中,加入10%钯-碳667mg,在室温搅拌。80分钟后,用硅藻土过滤,减压蒸除溶剂。残渣用硅胶柱(60g)纯化,用己烷-乙酸乙酯(15∶1~7∶2)洗脱,得到1H,1H-七氟丁基-4-氨基苯基醚1.7178g。
1H NMR(CDCl3)δppm:6.79(d,J=8.8Hz,2H),6.65(d,J=8.8Hz,2H),4.37(t,J=13.2Hz,2H),3.52(br s,1H),1.57(br s,1H)。
(87-3)
使用实施例(87-2)的化合物代替4-叔丁基环己胺,与实施例(9-3)同样进行操作,得到目的化合物226mg。
1H NMR(CD3OD)δppm:7.86(d,J=8.1Hz,1H),7.61(d,J=8.8Hz,2H),7.02(d,J=8.8Hz,2H),6.07(m,1H),5.68(m,2H),5.30(d,J=3.0Hz,1H),4.83(m,1H),4.64(t,J=13.2Hz,2H),4.52(m,1H),4.45(m,1H),4.25(m,1H),4.09(m,1H),3.74(m,1H),3.28(s,3H)。
IR(KBr)νcm-1:3398,3348,3101,2935,2852,1687,1602,1530,1513,1462,1414,1393,1354,1228。
实施例88(化合物编号2942)
Figure A0081465303861
使用3-氟苯胺代替4-叔丁基环己胺,与实施例(9-3)进行同样的操作,得到目的化合物90mg。
1H NMR(CD3OD)δppm:7.86(d,J=8.1Hz,1H),7.61(m,1H),7.42(m,1H),7.34(m,1H),6.88(m,1H),6.09(m,1H),5.76(m,2H),5.30(d,J=4.1Hz,1H),4.84(d,J=2.0Hz,1H),4.52(dd,J=1.9 and 6.2Hz,1H),4.45(t,J=3.9Hz,1H),4.25(dd,J=3.8 and 4.9Hz,1H),4.09(m,1H),3.74(t,J=5.5Hz,1H),3.26(s,3H)。
IR(KBr)νcm-1:3401,2937,2836,1685,1614,1604,1537,1493,1463,1446,1425,1393,1319,1267。
实施例89(化合物编号3502)
Figure A0081465303871
使用2,4-二氟苯胺代替4-叔丁基环己胺,与实施例(9-3)同样进行操作,得到目的化合物131mg。
1H NMR(CD3OD)δppm:7.88(d,J=8.1Hz,1H),7.74(m,1H),7.08(m,1H),6.99(m,1H),6.10(d,J=3.9,1H),5.81(d,J=4.0Hz,1H),5.75(d,J=8.1Hz,1H),5.30(d,J=4.6Hz,1H),4.76(d,J=1.7Hz,1H),4.53(dd,J=1.8 and 5.3Hz,1H),4.44(t,J=3.9Hz,1H),4.27(t,J=4.5Hz,1H),4.08(t,J=4.2Hz,1H),3.78(t,J=5.1Hz,1H),3.31(s,3H)。
IR(KBr)νcm-1:3417,2936,2836,1686,1611,1534,1498,1463,1432,1386,1330,1263。
实施例90(化合物编号3852)
Figure A0081465303881
使用2,3,4-三氟苯胺代替4-叔丁基环己胺,与实施例(9-3)同样进行合成,得到目的化合物168mg。
1H NMR(CD3OD)δppm:7.88(d,J=8.1Hz,1H),7.47(m,1H),7.15(m,1H),6.10(m,1H),5.80(d,J=3.9Hz,1H),5.75(d,J=8.1Hz,1H),5.31(d,J=4.4Hz,1H),4.76(d,J=1.8Hz,1H),4.52(m,1H),4.45(m,1H),4.26(m,1H),4.10(m,1H),3.77(t,J=5.3Hz,1H),3.36(s,3H)。
IR(KBr)νcm-1:3414,2939,2838,1686,1623,1547,1516,1468,1385,1294,1265。
实施例91(化合物编号5322)
(91-1)
将2-(4-硝基苯基)乙醇835mg溶于二氯甲烷30mL,在氮气氛围下-78℃搅拌。向其中用10分钟滴加入二乙基氨基硫三氟化物1.98mL溶于二氯甲烷20mL的溶液,慢慢升温至室温,同时进行搅拌。30分钟后,在冰冷却下,加入饱和碳酸氢钠水溶液50mL停止反应。二氯甲烷层再次用饱和氯化钠水溶液50mL洗净后,用无水硫酸镁干燥,减压蒸除溶剂。残渣用硅胶柱(25g)纯化,用己烷-乙酸乙酯(7∶2)洗脱,得到1-氟-2-(4-硝基苯基)乙烷359mg。
1H NMR(CDCl3)δppm:8.20(s,2H),7.40(s,2H),4.67(m,2H),3.10(m,2H)。
(91-2)
将实施例(91-1)的化合物353mg溶于甲醇4mL和四氢呋喃1mL的混合溶剂中,将所得溶液加入到溶有肼1水合物1.014mL的甲醇5mL溶液中,加入10%钯-碳200mg,在室温搅拌。1天后在80℃回流,1天后,追加10%钯-碳200mg,再回流9小时。反应后,用硅藻土过滤,减压蒸除溶剂。残渣溶于乙酸乙酯50mL中,用水50mL洗涤2次,用无水硫酸钠干燥后,蒸除溶剂。用硅胶柱(30g)纯化,用己烷-乙酸乙酯(4∶1)洗脱,得到1-氟-2-(4-氨基苯基)乙烷207mg。
1H NMR(CDCl3)δppm:6.10(m,2H),5.75(m,2H),3.70(m,1H),3.58(m,1H),2.68(br s,2H),1.99(m,2H)。
(91-3)
将实施例(91-2)的化合物207mg、化合物(VII)367mg、DIPC254μL、HOBT162mg溶于8mL DMF中,在0℃搅拌1小时,在室温搅拌1小时。减压蒸除溶剂,残渣用硅胶柱(30g)纯化,用二氯甲烷-甲醇(93∶7)洗脱,得到粗纯化物。将其用高效液相色谱纯化(HPLCInertsil PREP-ODS 30×250mm),用30%乙腈水溶液洗脱,冷冻干燥得到目的化合物359mg。
1H NMR(CD3OD)δppm:7.86(d,J=8.1Hz,1H),7.58(d,J=8.4Hz,2H),7.24(d,J=8.4Hz,2H),6.08(m,1H),5.77(d,J=3.7Hz,1H),5.75(d,J=8.1Hz,1H),5.30(d,J=4.3Hz,1H),4.84(d,J=2.1Hz,1H),4.64(t,J=6.5Hz,1H),4.53(m,2H),4.44(t,J=3.9Hz,1H),4.25(t,J=4.3Hz,1H),4.09(m,1H),3.74(t,J=5.5Hz,1H),3.28(s,3H),3.00(t,J=6.3Hz,1H),2.94(t,J=6.3Hz,1H)。
IR(KBr)νcm-1:3385,2937,2835,1685,1596,1528,1464,1414,1389,1323,1269。
实施例92(化合物编号4412)
Figure A0081465303901
使用4-甲硫基苯胺118μL、化合物(VII)218mg、DIPC169μL、HOBT102mg和DMF3mL,与实施例(91-3)同样进行合成,得到目的化合物51mg。
1H NMR(CD3OD)δppm:7.86(d,J=8.1Hz,1H),7.59(d,J=8.8Hz,2H),7.26(d,J=8.8Hz,2H),6.08(d,J=2.9Hz,1H),5.76(m,2H),5.30(d,J=4.4Hz,1H),4.83(m,1H),4.52(m,1H),4.44(m,1H),4.25(t,J=4.4Hz,1H),4.09(t,J=4.4Hz,1H),3.74(t,J=5.5Hz,1H),3.22(s,3H),2.46(s,3H)。
IR(KBr)νcm-1:3401,2924,2834,1685,1587,1522,1496,1463,1400,1326,1312,1271,1243。
实施例93(化合物编号4342)
使用4-三氟甲氧苯胺117μL、化合物(VII)201mg、DIPC158μL、HOBT95mg和DMF2.9mL,与实施例(91-3)同样进行合成,得到目的化合物201mg。
1H NMR(CD3OD)δppm:7.86(d,J=8.2Hz,1H),7.76(d,J=8.6Hz,2H),7.26(d,J=8.6Hz,2H),6.10(m,1H),5.76(m,2H),5.31(d,J=4.0Hz,1H),4.83(d,J=2.0Hz,1H),4.52(dd,J=1.9 and 6.2Hz,1H),4.45(dd,J=3.2 and 4.3Hz,1H),4.26(dd,J=3.8 and 4.8Hz,1H),4.11(t,J=4.5Hz,1H),3.74(t,J=5.5Hz,1H),3.27(s,3H)。
IR(KBr)νcm-1:3409,2938,2836,1686,1609,1533,1511,1464,1413,1268,1223,1203。
实施例94(化合物编号4482)
Figure A0081465303911
使用4-三氟甲基硫基苯胺121μL、化合物(VII)195mg、DIPC151μL、HOBT94mg和DMF2.8mL,与实施例(91-3)进行同样的合成,得到目的化合物102mg。
1H NMR(CD3OD)δppm:7.86(d,J=8.4Hz,1H),7.83(d,J=8.7Hz,2H),7.66(d,J=8.7Hz,2H),6.12(m,1H),5.75(m,2H),5.31(d,J=4.2Hz,1H),4.83(d,J=2.1Hz,1H),4.51(dd,J=1.9 and 4.3Hz,1H),4.45(m,1H),4.26(m,1H),4.10(m,1H),3.73(t,J=5.5Hz,1H),3.26(s,3H)。
IR(KBr)νcm-1:3408,3352,3104,2936,2836,1686,1589,1522,1463,1401,1315,1271,1243。
实施例95(化合物编号5532)
使用3-硝基苯胺102μL、化合物(VII)169mg、DIPC133μL、HOBT83mg和DMF2.9mL,与实施例(91-3)同样进行合成,得到目的化合物103mg。
1H MMR(CD3OD)δppm:8.70(m,1H),8.07(dd,J=2.1 and 7.9Hz,1H),8.01(dd,J=2.0 and 9.0Hz,1H),7.86(d,J=8.1Hz,1H),7.59(t,J=8.2Hz,1H),6.13(m,1H),5.75(m,2H),5.33(d,J=3.9Hz,1H),4.85(m,1H),4.51(dd,J=2.0 and 6.4Hz,1H),4.46(dd,J=3.2 and 4.3Hz,1H),4.26(m,1H),4.12(m,1H),3.74(t,J=5.5Hz,1H),3.26(s,3H)。
IR(KBr)νcm-1:3351,2937,2835,1685,1595,1533,1463,1430,1391,1355,1328,1300,1268,1248。
实施例96(化合物编号4762)
使用4-溴-3-甲基苯胺164mg、化合物(VII)203mg、DIPC158μL、HOBT95mg和DMF2.9mL,与实施例(91-3)进行同样的合成,得到目的化合物132mg。
1H NMR(CD3OD)δppm:7.86(d,J=8.2Hz,1H),7.61(d,J=2.4Hz,1H),7.49(d,J=8.7Hz,1H),7.44(dd,J=2.4 and 8.7Hz,1H),6.08(m,1H),5.75(m,2H),5.30(d,J=4.3Hz,1H),4.83(d,J=2.0Hz,1H),4.52(dd,J=2.0 and 6.0Hz,1H),4.44(dd,J=3.2 and 4.2Hz,1H),4.25(dd,J=3.8 and 4.8Hz,1H),4.09(m,1H),3.73(dd,J=5.2 and 6.0Hz,1H),3.27(s,3H),2.37(s,3H)。
IR(KBr)νcm-1:3338,2934,2834,1685,1605,1583,1530,1478,1463,1403,1390,1305,1270。
实施例97(化合物编号4832)
Figure A0081465303931
使用4-氟-3-硝基苯胺156mg、化合物(VII)229mg、DIPC180μL、HOBT108mg和DMF3.3mL,与实施例(91-3)进行同样的合成,得到目的化合物75mg。
1H NMR(CD3OD)δppm:8.55(dd,J=2.6 and 6.8Hz,1H),8.03(m,1H),7.85(d,J=8.1Hz,1H),7.42(dd,J=9.0 and 10.7Hz,1H),6.13(m,1H),5.75(m,2H),5.32(d,J=3.8Hz,1H),4.82(d,J=2.1Hz,1H),4.50(dd,J=2.0 and 6.2Hz,1H),4.46(dd,J=3.1 and 4.3Hz,1H),4.26(dd,J=3.5and 4.5Hz,1H),4.12(m,1H),3.72(dd,J=5.1 and 6.2Hz,1H),3.26(s,3H)。
IR(KBr)νcm-1:3370,2937,2836,1685,1604,1540,1501,1463,1406,1353,1265,1223。
实施例98(化合物编号842)
Figure A0081465303932
使用4-癸基苯胺211mg、化合物(VII)208mg、DIPC162μL、HOBT97mg和DMF3mL,与实施例(91-3)同样进行合成,得到目的化合物157mg。
1H NMR(CD3OD)δppm:7.86(d,J=8.1Hz,1H),7.52(d,J=8.4Hz,2H),7.16(d,J=8.4Hz,2H),6.07(m,1H),5.77(d,J=3.7Hz,1H),5.75(d,J=8.1Hz,1H),5.29(d,J=4.3Hz,1H),4.84(d,J=2.0Hz,1H),4.52(dd,J=1.8 and 6.0Hz,1H),4.44(dd,J=3.3 and 4.3Hz,1H),4.26(m,1H),4.09(t,J=4.3Hz,1H),3.75(t,J=5.5Hz,1H),3.29(s,3H),2.59(t,J=7.6Hz,2H),1.60(m,2H),1.30(m,14H),0.89(t,J=6.7Hz,3H)。
IR(KBr)νcm-1:3340,2925,2853,1687,1611,1595,1526,1464,1413,1319,1269。
实施例99(化合物编号6633)
Figure A0081465303941
使用1,3-亚苯基二胺115mg、化合物(VII)242mg、DIPC191μL、HOBT119mg和DMF3.5mL,与实施例(91-3)同样进行合成,得到目的化合物103mg。
1H NMR(CD3OD)δppm:7.87(d,J=8.1Hz,1H),7.08(m,1H),7.05(d,J=8.0Hz,1H),6.90(dd,J=2.0 and 8.0Hz,1H),6.52(dd,J=2.0 and 8.0Hz,1H),6.06(d,J=2.5Hz,1H),5.78(d,J=3.7Hz,1H),5.75(d,J=8.1Hz,1H),5.28(d,J=4.5Hz,1H),4.83(d,J=1.9Hz,1H),4.53(dd,J=2.0 and 5.9Hz,1H),4.43(t,J=3.9Hz,1H),4.26(t,J=4.2Hz,1H),4.07(t,J=4.3Hz,1H),3.75(t,J=5.4Hz,1H),3.30(s,3H)。
IR(KBr)νcm-1:3351,2936,2833,1685,1610,1540,1497,1459,1391,1325,1269。
实施例100(化合物编号6665)
将实施例(9-2)的化合物301mg,N,N-二甲基-1,4-亚苯基二胺二盐酸盐252mg、三乙胺336μL、DIPC216μL、HOBT130mg溶于DMF4mL中在室温搅拌。5小时后,减压蒸除溶剂,残渣用硅胶柱(30g)纯化,用二氯甲烷-甲醇(97.5∶2.5)洗脱,得到目的化合物231mg。
1H NMR(CD3OD)δppm:7.86(d,J=8.1Hz,1H),7.46(d,J=9.0Hz,2H),6.76(d,J=9.0Hz,2H),6.19(d,J=4.4Hz,1H),5.80(d,J=3.7Hz,1H),5.72(d,J=8.1Hz,1H),5.21(d,J=5.1Hz,1H),4.88(m,1H),4.84(m,1H),4.56(dd,J=2.2 and 5.9Hz,1H),4.45(m,1H),4.27(m,1H),3.82(t,J=5.5Hz,1H),3.30(s,3H),2.92(s,6H)。
(100-2)
Figure A0081465303952
将实施例(100-1)的化合物138mg溶于乙酸1.4mL、水0.6mL、乙二醇0.3mL的混合溶剂中,加热回流。2小时后,减压蒸除溶剂,残渣用硅胶柱(3g)纯化,用二氯甲烷-甲醇(95∶5)洗脱,得到目的化合物93mg。
1H NME(CD3OD)δppm:7.87(d,J=8.1Hz,1H),7.45(d,J=9.3Hz,2H),6.76(d,J=9.3Hz,2H),6.05(m,1H),5.78(d,J=3.7Hz,1H),5.75(d,J=8.1Hz,1H),5.28(d,J=4.4Hz,1H),4.83(d,J=2.0Hz,1H),4.52(dd,J=1.9 and 5.8Hz,1H),4.43(t,J=3.9Hz,1H),4.25(t,J=4.4Hz,1H),4.08(t,J=4.3Hz,1H),3.75(t,J=5.4Hz,1H),3.34(s,3H),2.91(s,6H)。
IR(KBr)νcm-1:3340,2930,2853,2802,1685,1616,1591,1525,1461,1408,1386,1324,1267。
实施例101(化合物编号6162)
Figure A0081465303961
使用2-(全氟丁基)乙胺(Szonyi,F.;Guennouni,F.;Cambon,A.制备2-(全氟烷基)乙胺的新方法,J.Fluorine Chem.(1991)55(1),85-92)代替4-叔丁基环己胺,与实施例(9-3)进行同样的合成,得到目的化合物94mg。
1H NMR(CD3OD)δppm:7.86(d,J=8.1Hz,1H),5.97(m,1H),5.80(d,J=4.2Hz,1H),5.75(d,J=8.1Hz,1H),5.22(d,J=4.4Hz,1H),4.66(d,J=2.0Hz,1H),4.49(dd,J=2.0 and 5.4Hz,1H),4.39(dd,J=3.2 and4.2Hz,1H),4.24(t,J=4.6Hz,1H),4.04(t,J=4.4Hz,1H),3.70(t,J=5.3Hz,1H),3.65(m,1H),3.57(m,1H),3.37(s,3H),2.48(m,2H)。
IR(KBr)νcm-1:3352,3101,2928,2854,1688,1532,1463,1395,1357,1332,1237。
实施例102 (化合物编号561)
将实施例(84-1)的化合物845mg和4-二甲基氨基吡啶480mg和苯基氯硫代甲酸酯353μL溶于氧化铝干燥的二氯甲烷30mL中,在室温搅拌。2小时后,用二氯甲烷300mL稀释,依次用各300mL的0.1N盐酸、饱和碳酸氢钠水溶液、饱和氯化钠水溶液洗涤,用无水硫酸钠干燥。减压蒸除溶剂,残渣用硅胶柱(110g)色谱纯化,用二氯甲烷-甲醇(97∶3)洗脱,得到目的化合物950mg。
1H NMR(CD3OD)δppm:7.81(d,J=8.1Hz,1H),7.53(d,J=8.5Hz,2H),7.41(t,J=7.9Hz,2H),7.29(t,J=7.3Hz,1H),7.18(d,J=8.5Hz,2H),7.10(d,J=7.5Hz,2H),6.19(d,J=3.7Hz,1H),6.09(d,J=4.9Hz,1H),5.89(t,J=5.1Hz,1H),5.75(d,J=8.1Hz,1H),5.29(d,J=4.6Hz,1H),4.93(m,1H),4.61(m,1H),4.48(t,J=5.2Hz,1H),4.27(t,J=4.8Hz,1H),3.35(s,3H),2.60(t,J=7.6Hz,2H),1.62(m,2H),1.45(s,6H),1.33(m,4H),0.90(t,J=7.0Hz,3H)。
(102-2)
Figure A0081465303981
将实施例(102-1)的化合物113mg溶于甲苯5mL中,加入三丁基氢化锡113μL和偶氮双异丁腈6mg,加热回流。1.5小时后,减压蒸除溶剂,残渣用硅胶柱(8g)色谱纯化,用二氯甲烷-甲醇(99∶1)洗脱,得到目的化合物68mg。
1H NMR(CD3OD)δppm:7.88(d,J=8.1Hz,1H),7.52(d,J=8.6Hz,2H),7.17(d,J=8.6Hz,2H),6.22(d,J=3.7Hz,1H),6.16(dd,J=6.0 and7.8Hz,1H),5.73(d,J=8.1Hz,1H),5.20(d,J=4.8Hz,1H),4.50(m,1H),4.44(t,J=5.5Hz,1H),4.06(m,1H),3.24(s,3H),2.59(t,J=7.7Hz,2H),2.40(m,1H),2.05(m,1H),1.61(m,2H),1.45(s,6H),1.34(m,4H),0.90(t,J=7.0Hz,3H)。
(102-3)
将实施例(102-2)的化合物68mg溶于甲醇2.5mL,加入大网状树脂15(H+)110mg,加热回流。140分钟后,滤除不溶物,减压蒸除溶剂。残渣用分取用薄层色谱纯化,用二氯甲烷-甲醇(85∶15)展开纯化,得到目的化合物39mg。
1H NMR(CD3OD)δppm:7.90(d,J=8.1Hz,1H),7.52(d,J=8.4Hz,2H),7.17(d,J=8.4Hz,2H),6.14(dd,J=6.0 and 7.8Hz,1H),6.06(d,J=2.5Hz,1H),5.76(d,J=8.1Hz,1H),5.27(d,J=4.6Hz,1H),4.49(m,1H),4.39(m,1H),4.06(m,1H),4.00(m,1H),3.23(s,3H),2.59(t,J=7.7Hz,2H),2.39(m,1H),2.00(m,1H),1.61(m,2H),1.32(m,4H),0.90(t,J=7.0Hz,3H)。
实施例103(化合物编号41)
将实施例85的化合物222mg溶于二氯甲烷6mL,加入水3.5mL搅拌。向其中用20分钟慢慢加入亚硝基硫酸2.99g,再搅拌5分钟后,用二氯甲烷100mL稀释,除去水层。用水4mL洗涤2次,用饱和氯化钠水溶液5mL洗净后,减压蒸除溶剂。将残渣溶于二氯甲烷10mL,加入含有重氮甲烷1.66mmol的乙醚溶液,在室温搅拌。15分钟后,减压蒸除溶剂,残渣用硅胶柱(7g)纯化,用二氯甲烷-甲醇(99∶1)洗脱,得到目的化合物123mg。
1H NMR(CD3OD)δppm:7.64(m,3H),7.36(m,2H),7.16(t,J=7.3Hz,1H),6.08(m,1H),5.94(d,J=8.1Hz,1H),5.90(d,J=3.7Hz,1H),5.77(m,1H),5.60(m,1H),5.34(m,1H),5.15(m,1H),4.56(m,1H),3.92(m,1H),3.86(s,3H),3.21(s,3H),2.11(s,3H),2.08(s,3H),2.03(s,3H)。
(103-2)
将实施例(103-1)的化合物120mg溶于甲醇4.2mL中,加入正十二烷胺1.19g,在室温搅拌。1天后,用Dowex 50W-×8(10g)柱纯化,用水-甲醇(1∶1)洗脱。减压蒸除溶剂,残渣用硅胶柱(5g)纯化,用二氯甲烷-甲醇(91∶1)洗脱,得到目的化合物11.9mg。
1H NMR(CD3OD)δppm:7.86(d,J=8.1Hz,1H),7.63(d,J=8.5Hz,2H),7.34(t,J=7.9Hz,2H),7.15(m,1H),6.09(d,J=3.5Hz,1H),5.79(d,J=4.1Hz,1H),5.75(d,J=8.1Hz,1H),5.23(d,J=5.0Hz,1H),4.53(dd,J=2.0 and 5.7Hz,1H),4.44(t,J=4.1Hz,1H),4.27(t,J=4.5Hz,1H),4.07(t,J=4.7Hz,1H),3.80(t,J=5.3Hz,1H),3.30(m,5H),1.55(m,2H),1.27(m,18H),0.89(t,J=6.8Hz,3H)。
IR(KBr)νcm-1:3351,3098,3062,2925,2854,1684,1600,1535,1498,1464,1444,1385,1321,1269。
实施例104(化合物编号6696)
将实施例(9-2)化合物807mg、苯胺265μL、二异丙基碳化二亚胺496μL、羟基苯并三唑393mg溶于二甲基甲酰胺16mL中,在冰冷却下搅拌1小时,在室温搅拌14小时。反应后,减压蒸除溶剂,残渣溶于乙酸乙酯200mL,依次用各200mL的0.05N盐酸水溶液和饱和碳酸氢钠水溶液洗净,用无水硫酸镁干燥。减压蒸除溶剂,残渣用硅胶柱(80g)纯化,用二氯甲烷-甲醇(96∶4)洗脱,得到目的化合物596mg。
1H NMR(CDCl3-CD3OD;19:1)δppm:8.53(s,1H),7.77(d,J=8.1Hz,1H),7.61(m,2H),7.35(m,2H),7.16(m,1H),6.48(d,J=3.7Hz,1H),5.77(d,J=2.9Hz,1H),5.74(d,J=8.1Hz,1H),4.78(m,4H),4.37(m,1H),4.12(m,1H),3.99(dd,J=5.1 and 6.6Hz,1H),3.41(s,3H),1.51(s,3H),1.47(s,3H)。
IR(KBr)νcm-1:3418,3341,3100,3064,2989,2936,2833,1691,1599,1533,1498,1445,1383,1321,1299,1269,1244,1218。
(104-2)
将实施例(104-1)的化合物593mg溶于二甲基甲酰胺2mL中,加入叔丁基二甲基甲硅烷基氯311mg和咪唑140mg,在室温搅拌。5小时后,追加叔丁基二甲基甲硅烷基氯165mg和咪唑70mg,进一步搅拌。16小时后,减压蒸除溶剂,残渣溶于乙酸乙酯100mL,用水100mL洗净后,用无水硫酸镁干燥。减压蒸除溶剂,残渣用硅胶柱(80g)纯化,用二氯甲烷-甲醇(98∶2)洗脱,得到目的化合物632mg。
1H NMR(CDCl3)δppm:8.47(br s,1H),8.42(br s,1H),7.86(d,J=7.8Hz,1H),7.62(d,J=7.8Hz,2H),7.36(m,2H),7.17(m,1H),7.07(br s,1H),6.52(d,J=3.9Hz,1H),5.87(br s,1H),5.72(m,1H),5.62(s,1H),4.85(m,1H),4.82(m,1H),4.70(d,J=7.8Hz,1H),4.65(d,J=2.9Hz,1H),4.48(m,1H),4.08(dd,J=5.9 and 7.8Hz,1H),3.85(dd,J=3.9 and4.9Hz,1H),3.31(s,3H),1.52(s,3H),1.47(s,3H),0.92(s,9H),0.21(s,3H),0.15(s,3H)。
IR(KBr)νcm-1:3458,3417,3340,3198,3098,3064,2988,2952,2933,2897,2857,1695,1600,1533,1499,1444,1382,1320,1298,1251,1220。
(104-3)
Figure A0081465304022
将实施例(104-2)的化合物318mg溶于二甲基甲酰胺5ml中,加入1,8-二氮杂双环[5.4.0]-7-十一碳烯102μL和新戊酰氧甲基氯100μL,在室温搅拌。23小时后,追加1,8-二氮杂双环[5.4.0]-7-十一烯102μL和新戊酰氧甲基氯100μL,进一步搅拌。4小时后,减压蒸除溶剂,残渣溶于乙酸乙酯200mL,用水200mL洗净后,用无水硫酸镁干燥。减压蒸除溶剂,残渣用硅胶柱(40g)纯化,用己烷-乙酸乙酯(1∶1)洗脱,得到目的化合物273mg。
1H NMR(CDCl3)δppm:8.40(br s,1H),7.90(d,J=8.0Hz,1H),7.61(d,J=7.8Hz,2H),7.36(t,J=7.8Hz,2H),7.17(m,1H),7.05(br s,1H),6.53(d,J=3.9Hz,1H),5.93(s,1H),5.79(d,J=8.0Hz,1H),5.74(brs,1H),5.68(s,1H),4.89(m,1H),4.81(m,1H),4.71(d,J=7.8Hz,1H),4.62(d,J=2.0Hz,1H),4.38(m,1H),4.08(m,1H),3.84(m,1H),3.31(s,3H),1.52(s,3H),1.47(s,3H),1.10(s,9H),0.94(s,9H),0.22(s,3H),0.13(s,3H)。
IR(KBr)νcm-1:3466,3422,3350,3194,3103,3064,2958,2934,2906,2858,1731,1685,1600,1533,1499,1480,1456,1445,1404,1375,1321,1279,1251,1220。
(104-4)
将实施例(104-3)的化合物272mg溶于四氢呋喃340μL中,加入含有1M浓度的四丁基氟化铵的四氢呋喃溶液340μL,在室温放置。30分钟后,追加上述溶液100μL,再放置1小时。减压蒸除溶剂,残渣用硅胶柱(40g)纯化,用二氯甲烷-甲醇(99∶1)洗脱,得到目的化合物218mg。
1H NMR(CDCl3)δppm:8.31(s,1H),7.75(d,J=8.1Hz,1H),7.58(d,J=8.1Hz,2H),7.35(m,2H),7.17(t,J=7.3Hz,1H),7.07(br s,1H),6.51(d,J=4.4Hz,1H),5.92(m,2H),5.86(d,J=2.9Hz,1H),5.81(d,J=8.1Hz,1H),5.76(br s,1H),4.81(m,2H),4.72(m,2H),4.40(br s,1H),4.10(m,1H),4.05(m,1H),3.44(s,3H),2.17(br s,1H),1.51(s,3H),1.47(s,3H),1.19(s,9H)。
IR(KBr)νcm-1:3459,3422,3355,3105,3063,2982,2935,2877,1728,1682,1600,1533,1499,1481,1456,1445,1404,1376,1321,1280,1241,1219。
(104-5)
Figure A0081465304041
将实施例(104-4)的化合物216mg溶于甲醇3mL,加入100mg的大网树脂15,加热回流下搅拌。3小时后,滤除不溶物,减压蒸除溶剂,残渣用硅胶柱(20g)纯化,用二氯甲烷-甲醇(96∶4)洗脱,得到目的化合物146mg。
1H NMR(CD3OD)δppm:7.94(d,J=8.1Hz,1H),7.64(d,J=8.7Hz,2H),7.34(d,J=8.0,2H),7.15(t,J=7.3Hz,1H),6.08(m,1H),5.89(m,3H),5.79(d,J=3.4Hz,1H),5.31(d,J=4.3Hz,1H),4.55(dd,J=1.9 and6.2Hz,1H),4.44(t,J=3.9Hz,1H),4.27(m,1H),4.10(m,1H),3.73(dd,J=5.1 and 6.2Hz,1H),3.27(s,3H),1.17(s,9H)。
IR(KBr)νcm-1:3411,3368,3108,2973,2935,2877,1726,1671,1599,1534,1497,1481,1458,1445,1405,1376,1324,1280,1240。
实施例105(化合物编号6707)
Figure A0081465304051
用3,4-二氟苯胺代替苯胺,与实施例(104-1)同样进行合成,得到目的化合物1.405g。
1H NMR(CD3OD)δppm:7.84(d,J=8.1Hz,1H),7.76(m,1H),7.40(m,1H),7.23(m,1H),6.23(d,J=3.7Hz,1H),5.79(d,J=3.7Hz,1H),5.72(d,J=8.1Hz,1H),5.26(d,J=4.4Hz,1H),4.83(m,1H),4.52(m,1H),4.47(m,1H),4.27(dd,J=3.7 and 5.1Hz,1H),3.80(m,1H),3.27(s,3H),1.45(s,3H),1.44(s,3H)。
(105-2)
使用实施例(105-1)的化合物1g,与实施例(104-2)进行同样的合成,得到目的化合物981mg。
1H NMR(CD3OD)δppm:7.92(d,J=8.1Hz,1H),7.76(m,1H),7.40(m,1H),7.25(m,1H),6.22(d,J=3.7Hz,1H),5.72(d,J=8.1Hz,1H),7.72(d,J=3.7Hz,1H),5.24(d,J=4.4Hz,1H),4.88(d,J=2.2Hz,1H),4.85(m,1H),4.58(m,1H),4.43(m,1H),4.38(m,1H),3.72(m,1H),3.26(s,3H),1.46(s,3H),1.45(s,3H),0.89(s,9H),0.13(s,3H),0.10(s,3H)。
IR(KBr)νcm-1:3415,3341,3101,2988,2933,2897,2858,1694,1617,1518,1461,1439,1413,1383,1265。
(105-3)
Figure A0081465304061
将实施例(105-2)的化合物717mg和碳酸钾232mg溶于二甲基甲酰胺18mL,加入1-氯乙基己酸酯530mg,在冰冷却下搅拌5分钟,再在60℃搅拌6小时。反应后,减压蒸除溶剂,残渣用硅胶柱(32g)纯化,用二氯甲烷-甲醇(98.5∶1.5)洗脱,得到目的化合物230mg。
1H NMR(CDCl3)δppm:8.54(s,1H),7.78(m,2H),7.22-7.00(m,5H),6.51(m,1H),5.85(m,1H),5.72(d,J=8.1Hz,1H),5.67(s,1H),4.85(m,1H),4.80(m,1H),4.65(m,1H),4.60(m,1H),4.37(m,1H),4.07(m,1H),3.81(m,1H),3.30(s,3H),2.33(m,2H),1.79(m,2H),1.48(s,3H),1.25(m,4H),0.95(s,9H),0.85(m,3H),0.23(s,3H),0.18 and 0.17(2s,3H)。
(105-4)
Figure A0081465304062
使用实施例(105-3)的化合物282mg,与实施例(104-4)同样进行合成,得到目的化合物177mg。
1H NMR(CD3OD)δppm:7.85(d,J=8.1Hz,1H),7.78(m,1H),7.40(m,1H),7.22(m,2H),6.21(m,1H),5.76(m,2H),5.27(m,1H),4.82(m,1H),4.57(m,2H),4.47(m,1H),4.28(m,1H),3.78(m,1H),3.26(s,3H),2.32(t,J=7.3Hz,2H),1.76(d,J=6.6Hz,2H),1.59(m,2H),1.43(m,6H),1.30(m,5H),0.90(m,3H)。
IR(KBr)νcm-1:3442,3106,2987,2957,2935,2874,1718,1677,1617,1537,1518,1444,1414,1383,1280,1239,1214。
(105-5)
Figure A0081465304071
使用实施例(105-4)的化合物175mg,与实施例(104-5)同样进行合成,得到目的化合物54mg。
1H NMR(CD3OD)δppm:7.86(d,J=8.1Hz,1H),7.77(m,1H),7.41(m,1H),7.22(m,2H),6.08(m,1H),5.75(m,2H),5.30(d,J=4.4Hz,1H),4.82(d,J=2.2Hz,1H),4.52(m,1H),4.42(m,1H),4.24(m,1H),4.10(m,1H),3.68(m,1H),3.24(s,3H),2.32(t,J=7.3Hz,2H),1.75(d,J=5.9Hz,3H),1.59(m,2H),1.29(m,4H),0.89(m,3H)。
IR(KBr)νcm-1:3412,3349,3105,2957,2935,2873,1719,1665,1617,1536,1518,1444,1414,1384,1320,1279,1241,1210。
实施例106(化合物编号6703)
Figure A0081465304072
(106-1)
Figure A0081465304081
使用1-氯乙基乙基碳酸酯代替1-氯乙基己酸酯,与实施例(105-3)同样进行合成,得到目的化合物152mg。
1H NMR(CDCl3)δppm:8.54(s,1H),7.78(m,2H),7.15(m,3H),7.00(m,1H),6.50(m,1H),5.73(m,2H),5.67(d,J=3.7Hz,1H),4.85(m,1H),4.80(m,2H),4.65(m,1H),4.59(d,J=2.2Hz,1H),4.39(m,1H),4.18(m,3H),4.08(m,1H),3.82(m,1H),3.31(s,3H),1.85(m,2H),1.51(s,3H),1.46(s,3H),1.30(m,5H),0.95(s,9H),0.24 and 0.23(2s,3H),0.15(s,3H)。
(106-2)
使用实施例(106-1)的化合物194mg,与实施例(104-4)进行同样的合成,得到目的化合物111mg。
1H NMR(CD3OD)δppm:7.84(m,1H),7.77(m,1H),7.40(m,1H),7.23(m,1H),7.12(m,1H),7.21(m,1H),5.75(m,2H),5.26(m,1H),4.83(m,1H),4.54(m,1H),4.46(m,1H),4.28(m,1H),4.15(m,2H),3.78(m,1H),3.27(s,3H),1.80(d,J=6.6Hz,3H),1.45(s,3H),1.44(s,3H),1.26(m,3H)。
(106-3)
Figure A0081465304091
使用实施例(106-2)的化合物110mg,与实施例(104-5)同样进行合成,得到目的化合物42mg。
1H NMR(CD3OD)δppm:7.86(d,J=8.1Hz,1H),7.77(m,1H),7.41(m,1H),7.23(m,1H),7.12(m,1H),6.08(m,1H),5.77(d,J=8.1Hz,1H),5.74(m,1H),5.30(d,J=3.7Hz,1H),4.82(d,J=2.2Hz,1H),4.52(m,1H),4.43(m,1H),4.24(m,1H),4.15(m,2H),4.10(m,1H),3.68(m,1H),3.24(s,3H),1.79(d,J=5.9Hz,3H),1.25(m,3H)。
实施例107(化合物编号6706)
使用1-氯乙基环己基碳酸酯代替1-氯乙基己酸酯,与实施例(105-3)同样进行合成,得到目的化合物194mg。
(107-2)
使用实施例(107-1)的化合物193mg,与实施例(104-4)进行同样的合成,得到目的化合物122mg。
(107-3)
使用实施例(107-2)的化合物120mg,与实施例(104-5)进行同样的合成,得到目的化合物51mg。
1H NMR(CD3OD)δppm:7.87(d,J=8.1Hz,1H),7.78(m,1H),7.42(m,1H),7.23(m,1H),7.12(m,1H),6,08(m,1H),5.79(d,J=8.1Hz,1H),5.75(m,1H),5.31(d,J=4.4Hz,1H),4.82(m,1H),4.58(m,1H),4.52(m,1H),4.42(m,1H),4.25(m,1H),4.10(m,1H),3.68(m,1H),3.24(s,3H),1.85(m,2H),1.79(d,J=5.9Hz,3H),1.72(m,2H),1.55-1.25(m,6H)。
实施例108(化合物编号6730)
Figure A0081465304103
(108-1)
将N-叔丁氧羰基-6-氨基己酸106mg溶于二氯甲烷16mL中,加入三乙胺77μL,在氮气氛围下于-78℃搅拌,加入氯甲酸乙酯53μL。1小时后,升温至0℃,再搅拌40分钟后,滴加入ホロチン盐酸盐115mg和三乙胺154μL溶于二甲基甲酰胺14mL的溶液。过30分钟后,升温至室温,再搅拌90分钟。反应后,减压蒸除溶剂,残渣溶于乙酸乙酯50mL,分别用50mL的水和饱和氯化钠水溶液洗净,用无水硫酸镁干燥。减压蒸除溶剂,残渣用硅胶柱(5g)纯化,用二氯甲烷-甲醇(99∶1)洗脱,得到目的化合物84mg。
1H NMR(CDCl3)δppm:8.96(br s,1H),8.21(br s,1H),6.79(s,1H),4.63(br s,1H),3.10(m,2H),2.38(t,J=7.6Hz,2H),1.75-1.40(m,15H)。
(108-2)
Figure A0081465304112
将实施例(108-1)的化合物84mg溶于三氟乙酸-水(4∶1)30mL,在室温搅拌。15分钟后,减压蒸除溶剂,用乙醇共沸数次得到黄色固体。往其中加入化合物(VII)107mg、HOBT 48mg,溶在二甲基甲酰胺1.5mL中,进一步加入三乙胺46μL和DIPC70μL,在室温搅拌。3小时后,减压蒸除溶剂,残渣用硅胶柱(6g)纯化,用二氯甲烷-甲醇(4∶1)洗脱,得到目的化合物75mg。
1H NMR(CD3OD)δppm:7.87(d,J=8.2Hz,1H),5.94(m,1H),5.81(d,J=4.2Hz,1H),5.75(d,J=8.2Hz,1H),5.21(d,J=4.7Hz,1H),4.69(d,J=1.8Hz,1H),4.50(dd,J=2.0 and 5.2Hz,1H),4.38(m,1H),4.24(t,J=4.5Hz,1H),4.02(t,J=4.3Hz,1H),3.71(t,J=5.1Hz,1H),3.38(s,3H),3.30(m,2H),2.40(t,J=7.4Hz,2H),1.70(m,2H),1.60(m,2H),1.40(m,2H)。
实施例109(化合物编号6732)
用N-叔丁氧羰基-8-氨基辛酸代替N-叔丁氧羰基-6-氨基己酸,与实施例(108-1)进行同样的合成,得到目的化合物162mg。
1H NMR(CDCl3)δppm:8.62(br s,1H),7.78(br s,1H),6.76(s,1H),4.53(br s,1H),3.08(m,2H),2.35(t,J=7.3Hz,2H),1.75-1.30(m,19H)。
(109-2)
Figure A0081465304122
使用实施例(109-1)的化合物代替实施例(108-1)的化合物,与实施例(108-2)同样进行合成,得到目的化合物43mg。
1H NMR(CD3OD)δppm:7.87(d,J=8.8Hz,1H),7.06(s,1H),5.94(d,J=4.4Hz,1H),5.81(d,J=4.4Hz,1H),5.75(d,J=8.8Hz,1H),5.21(d,J=4,4Hz,1H),4.69(d,J=1.5Hz,1H),4.50(dd,J=2.2 and 5.1Hz,1H),4.38(m,1H),4.24(m,1H),4.02(t,J=4.4Hz,1H),3.71(t,J=5.1Hz,1H),3.38(s,3H),3.25(m,2H),2.39(t,J=7.4Hz,2H),1.65(m,2H),1.55(m,2H),1.38(br s,6H)。
制备例1灰色链霉菌(Streptomyces griseus)SANK60196(FERMBP-5420)株的培养
在加入下述组成的预培养基500mL的2L锥形烧瓶(种烧瓶)中无菌接种4铂环量SANK60196株,接着将4支该烧瓶在旋转振荡机中在23℃,210rpm振动,进行3天的预培养。
预培养基:在1000ml的自来水中含有下述成分。
      麦芽糖                     30g
      肉提取物                   5g
      聚胨                       5g
      氯化钠                     5g
      碳酸钙                     3g
      消泡剂CB442                50mg
      (日本油脂社制)
将pH调整至7.4后在121℃灭菌30分钟。
该培养如下进行。即,在2台加入了下述主培养基15L的30L发酵罐中,将预培养液以3%(容量/容量:以下记为“v/v”)接种。在23℃培养开始后第6小时加入过滤灭菌的S-(2-氨基乙基)-L-半胱氨酸盐酸盐,达到最终浓度10mM,之后,通气搅拌6天进行培养。
主培养基:在1000ml自来水中含有下述成分
麦芽糖                          30g
酵母提取物                      5g
(Difco社制)
肉提取物                        5g
聚胨                              5g
氯化钠                            5g
碳酸钙                            3g
消泡剂CB442                       50mg
(日本油脂社制)
将pH调整至7.4后,在125℃灭菌30分钟。
制备例2、化合物(VI)的纯化
将制备例1中得到的培养终了液(30L)用硅藻土545(CeliteCorporation社制)作为过滤助剂进行过滤。
对于以下的纯化,用下述柱和分析条件的HPLC监测活性馏分。
柱:Senshu Pak ODS-H-2151
    6φ×150mm(センシュ一科学社制)
溶剂:含有4%乙腈的0.04%三氟乙酸水溶液
流速:1.0ml/分
检测:UV210nm
保留时间:21.2分钟
将所得液体30L供到填充了迪阿翁离子交换树脂HP-20(三菱化学社制)的柱(6L)中。之后,将柱子用12L的纯水洗净,将直接流出组分和洗涤组分合并(以下,将该合并组分记为“直接流出·洗涤组分”)。用12L的10%丙酮水溶液洗脱出吸着物质。将洗脱出的馏分浓缩,蒸除丙酮后,冷冻干燥,得到39g的粗粉末。
将该粗粉末溶于200ml的纯水中,供到填充了迪阿翁离子交换树脂CHP-20P(三菱化学社制)的柱(2L)中。之后,将柱子用4L的纯水和4L10%甲醇水溶液洗净,吸着物质用4L15%甲醇水溶液、4L20%甲醇水溶液洗脱。将15%甲醇水馏分的2~4L部分和20%甲醇水溶液馏分合并浓缩,蒸除甲醇后,冷冻干燥,得到8.9g粉末。
将该粉末溶于200mL的纯水中,供到填充了トョパ一ルHW40F(東ソ一社制)的柱(1L)中,将柱子用纯水展开,将每100mL洗脱液作为一个馏分,用上述HPLC测定的保留时间21.2分的活性物质在第5~10馏分被洗脱出来。将该馏分浓缩后,冷冻干燥,得到2.7g粉末。
将该粉末溶于200mL水中,供到用含有4%乙腈的0.04%三氟乙酸水溶液平衡的HPLC柱(YMC-Pack ODS-1050-20-SR:100φ×500mm:ヮィェムシィ社制),将柱子用含有4%乙腈的0.04%三氟乙酸水溶液以208ml/分的速度展开。每1L洗脱液作为一个馏分,活性物质在第6和7馏分被洗脱出。
合并这些馏分,用エバポ一ル(大川原制作所社制)浓缩至200mL后,冷冻干燥,得到99mg的粉末。将该粉末悬浮于5ml的蒸馏水中,滤除不溶物。滤液用旋转蒸发器浓缩至2ml,通过冷冻干燥,得到87mg化合物(VI)纯品。
化合物(VI)具有下述物理化学性质。1)    物质的性状;白色粉末状物质2)    溶解性:水中可溶,微溶于甲醇,正己烷、氯仿中不溶3)    分子式;C18H23N3O124)    分子量:473(通过FAB质谱法测定)5)    用高分辨FAB质谱法测定的精确质量,[M+H]+如下所示:
      实测值;474.1349
      计算值:474.13596)    紫外吸收光谱:在水中测定的紫外吸收光谱的最大吸收如下所示:  251nm(ε10,000)7)    旋光度:在水中测定的旋光度具有如下所示的值:
    [α]D 20:+115°(c0.28)8)    红外吸收光谱:用溴化钾(KBr)片剂法测定的红外吸收光谱具有如下所示的最大吸收:
3410,2955,1683,1464,1441,1396,1309,1267,1206,1138,1115,1088,1062,1023cm-19)1H-核磁共振谱:在氘代二甲基亚砜中,内标使用四甲基硅烷测定,1H-核磁共振谱如下所示:
3.24(3H,s),3.52(1H,dd,J=4.5,6.1Hz),3.72(3H,s),3.98(1H,m),4.10(1H,m),4.25(1H,m),4.29(1H,d,J=2.0Hz),4.33(1H,dd,J=2.0,6.1Hz),5.05(1H,d,J=3.9Hz),5.16(1H,d,J=6.8Hz),5.45(1H,d,J=4.2Hz),5.54(1H,d,J=5.9Hz),5.61(1H,d,J=3.3Hz),5.61(1H,d,J=8.1Hz),5.93(1H,dd,J=1.3,2.9Hz),7.56(1H,br.s),7.69(1H,br.s),7.74(1H,d,J=8.1Hz)ppm.10)13C-核磁共振谱:在氘代二甲基亚砜中,内标使用四甲基硅烷测定,13C-核磁共振谱如下所示:
  52.0(q),57.3(q),61.5(d),64.9(d),72.1(d),75.4(d),78.2(d),81.3(d),89.0(d),99.2(d),101.2(d),114.2(d),139.2(s),139.8(d),150.3(s),161.8(s),163.1(s),170.1(s)ppm.11)高效液相色谱(high performance liquid chromatography:以下记为“HPLC”。)分析:
柱:センシュ一パックODS-H-2151
   6φ×150mm(センシュ一科学社制)
溶剂:含有4%乙腈的0.04%三氟乙酸水溶液
流速:1.0ml/分
检测:UV 210nm
保留时间:21分钟
制备例3化合物(VII)的纯化
对于以下的纯化,用下述柱和分析条件的HPLC监测活性馏分。
柱:Senshu Pak ODS-H-2151
   6φ×150mm(センシュ一科学社制)
溶剂:0.04%三氟乙酸水溶液
流速:1.5ml/分
检测:UV 210nm
保留时间:18分钟
将制备例2得到的直接流出·洗涤馏分42L的pH用6N氢氧化钠调整至9后,供到填充了迪阿翁离子交换树脂PA316(Cl-)(三菱化学社制)的柱(8.5L)中。之后,将柱子用27L的纯水洗净后,用0.1N盐酸将吸着物质洗脱出。
将洗脱液的pH用6N的氢氧化钠调整至7后,将该洗脱液供到活性炭柱(2L)中。将柱子用8L的纯水洗净后,用含10%丙酮的0.5N氨水8L将活性物质洗脱出。将该洗脱液浓缩,冷冻干燥,得到28g粉末。
将该粉末溶于400ml的蒸馏水中,调整至pH3.0后,供到用纯水调制过填充了迪阿翁离子交换树脂CHP-20P(三菱化学社制)的柱(2L)中。回收通过液和水洗涤液,浓缩,冷冻干燥,得到12g粘性物质。
将所得粘性物质溶于200ml蒸馏水中,用三氟乙酸调整至pH3.3之后,再次提供到用0.04%三氟乙酸水溶液平衡的迪阿翁离子交换树脂CHP-20P(三菱化学社制)柱(1L)中。将柱子用2L 0.04%三氟乙酸水溶液展开,收集0.8~1.4L之间的洗脱出的馏分(H馏分)后,将洗脱液切换为2L蒸馏水进行洗脱。将蒸馏水洗脱出的馏分2L(F馏分)浓缩,冷冻干燥,得到605mg的粉末。
将605mg的F馏分的冷冻干燥粉末溶于15ml水中,各1ml供到用0.04%三氟乙酸水溶液平衡的HPLC柱(Senshu Pak ODS-H-5251:20φ×250mm:センシュ一科学社制),以10ml/分钟展开。检测出活性馏分在紫外210nm的吸收,收集15次保留时间在29分钟~31分钟洗脱出的峰。所得馏分用旋转蒸发器浓缩后,冷冻干燥,得到134mg化合物(VII)纯品。
化合物(VII)具有下述物理化学性质。1)  物质的性状:白色粉末状物质2)  溶解性:水中可溶,微溶于甲醇,正己烷、氯仿中不溶3)  分子式;C17H21N3O124)  分子量:459(通过FAB质谱法测定)5)  用高分辨FAB质谱法测定的精确质量,[M+H]+如下所示:
      实测值;460.1201
      计算值:460.12036)  紫外吸收光谱:在水中测定的紫外吸收光谱的最大吸收如下所示:  262nm(ε7,000)7)  旋光度:在水中测定的旋光度具有如下所示的值:
    [α]D 20:+111°(c0.41)8)  红外吸收光谱:用溴化钾(KBr)片剂法测定的红外吸收光谱具有如下所示的最大吸收:3391,2941,1684,1466,1400,1333,1269,1205,1137,1115,1062,1020cm-19)1H-核磁共振谱:在氘代水中,水的信号为4.75ppm测定,1H-核磁共振谱如下所示:
                                                   3.37(3H,s),3.79(1H,dd,J=5.1,6.4Hz),4.17(1H,ddd,J=1.6,3.4,4.6Hz),4.38(1H,dd,J=3.5,5.1Hz),4.48(1H,dd,J=2.4,6.4Hz),4.49(1H,ddd,J=0.6,2.7,4.6Hz),4.69(1H,d,J=2.4Hz),5.32(1H,dd,J=0.6,3.4Hz),5.77(1H,d,J=3.5Hz),5.90(1H,d,J=8.1Hz),6.11(1H,dd,J=1.6,2.7Hz),7.75(1H,d,J=8.1Hz)ppm.10)13C-核磁共振谱:在氘代水中,内标使用1,4-二噁烷(67.4ppm)测定,13C-核磁共振谱如下所示:58.6(q),62.7(d),65.5(d),72.7(d),76.3(d),78.8(d),91.2(d),100.0(d),102.7(d),114.8(d),140.7(s),141.9(d),152.1(s),165.4(s),167.0(s),173.9(s)ppm.11)HPLC分析:柱:センシュ一パックODS-H-2151
  6φ×150mm(センシュ一科学社制)
溶剂:0.04%三氟乙酸水溶液
流速:1.5ml/分
检测:UV 210nm
保留时间:18分钟。
制备例4.化合物(VII)的制备方法(化合物(VI)的水解)
将制备例2得到的化合物(VI)4.4mg溶于0.5ml蒸馏水中。滴加入0.5ml的0.02N氢氧化钠水溶液后,滴加入1ml的0.1N氢氧化钠水溶液,在室温放置50分钟。将反应液用1N的盐酸中和后,供给到2ml活性炭柱上。将柱子用8ml蒸馏水洗净后,用8ml含有10%丙酮的0.5N氨水将反应物洗脱出来。
将该洗脱液浓缩至700μL后,将230μL供给到用0.04%三氟乙酸水溶液平衡的HPLC柱(Senshu Pak ODS-H-4251:10φ×250mm:センシュ一科学社制),以流速4ml/分钟展开。检测出活性物质在紫外210nm的吸收,收集保留时间在25分钟~30分钟洗脱出的峰。该操作重复三次。所得馏分用旋转蒸发器浓缩后,冷冻干燥,得到2.6mg化合物(VII)。
试验例1.体外抗菌活性(1)
测定本发明化合物对鸟分枝杆菌NIHJ1605株的最小生长抑制浓度。向Middleblook 7H9肉汤中加入吐温(Tween)80(0.1%),高压蒸气灭菌后,加入Middleblook ADC Enrichment(20%),之后,分别注入小试验管,每管0.8ml。向其中添加稀释为2倍系列的本发明各化合物0.1ml(以下简称为含有药剂的培养基。)另外,将鸟分枝杆菌NIHJ1605在吐温蛋培养基预培养10~14天的菌落取到装有吐温80和玻璃珠的试验管中,充分混合后,加入Middleblook 7H9肉汤,形成均一菌液,将菌液调节为OD625nm=0.10(菌量约为1×108CFU/ml),稀释100倍。将该菌液各0.1ml接种到上述含有各药剂的培养基中(最终菌量约为1×105CFU/ml),在37℃需氧培养6天,判定在试管底部未见形成直径1mm以上菌块的最小药剂量,将其作为MIC(μg/ml)。结果如表7所示。
[表7]对鸟分枝杆菌NIHJ1605的抗菌力
化合物编号                         最小抑制浓度(μg/ml)
卡普拉霉素(カプラマィシン)                  8
5(实施例80)                                 0.25
6(实施例81)                                 0.5
7(实施例82)                                 1
9(实施例83)                                 2
20(实施例85)                                4
142(实施例44)                               2
163(实施例86)                               4
352(实施例54)                               4
562(实施例55)                               1
982(实施例58)                               2
1472(实施例50)                              2
2242(实施例62)                              1
2312(实施例64)                              0.25
2382(实施例63)                          0.5
3012(实施例45)                          4
3712(实施例57)                          2
4132(实施例60)                          2
5742(实施例59)                          4
6351(实施例5)                           4
6411(实施例14)                          1
6526(实施例32)                          4
6631(实施例79)                          0.5
试验例2.体外抗菌活性(2)
通过用液体稀释法测定被检化合物对结核分枝杆菌的最小生长抑制浓度(MIC)。将被检化合物溶于二甲基亚砜(DMSO)或蒸馏水,用50%丙酮或蒸馏水稀释。将该稀释液进一步用添加了0.05%的吐温80、0.2%葡萄糖和10%Middlebrook ADC Enrichment的Middlebrook7H9肉汤稀释。各化合物2倍阶段稀释使用添加了0.05%的吐温80、0.2%葡萄糖和10%Middlebrook ADC Enrichment的Middreblook7H9肉汤进行。DMSO和丙酮的最终浓度分别不超过0.05%和2.5%。将在小川培养基平板上增殖的菌在添加了0.05%的吐温80、0.2%葡萄糖和10%Middlebrook ADC Enrichment的Middlebrook 7H9肉汤中均一悬浮,调节至用分光光度计测定达到约1×107CFU/ml。将该悬浮菌液用添加了0.05%的吐温80、0.2%葡萄糖和10%Middlebrook ADC Enrichment的Middlebrook 7H9肉汤稀释。达到最终接种菌量为1×106CFU/ml。在各试验管中将稀释菌液和稀释化合物混合,在35℃培养10至21天。在确认不含化合物的对照试验管有明显增殖的点判定MICs。MICis为肉眼观察到的产生增殖抑制的最小化合物浓度。
被检化合物对结核分枝杆菌的最小生长抑制浓度(MICs)如表8所示。
[表8]化合物3712对结核分枝杆菌的MICs(μg/ml)
   化合物                                      菌株
              结核分枝杆菌Kato                   结核分枝杆菌No.743712(实施例57)             1                                 8
试验中使用的菌株结核分枝杆菌No.74对利福平有耐性(MIC128μg/ml),但是本发明的化合物3712(实施例57)显示良好的抗菌活性。制剂例1.胶囊剂
  实施例43的化合物                                 100mg
       乳糖                                        100mg
     玉米淀粉                                    148.8mg
     硬脂酸镁                                      1.2mg
       全量                                        350mg
将上述处方的粉末混合,通过60目的筛子后,将该粉末装入明胶胶囊,制成胶囊剂。
制剂例2.液剂1
制备液剂达到含有实施例57的化合物10%(w/w)、氯化苄烷铵0.04%(w/w)、苯乙醇0.40%(w/w)、纯化水89.56%(w/w)。
制剂例3.液剂2
制备液剂达到含有实施例57的化合物10%(w/w)、氯化苄烷铵0.04%(w/w)、聚乙二醇400为10%(w/w)、丙二醇30%(w/w)、纯化水39.96%(w/w)。
制剂例4.粉末剂
制成粉末剂达到含有实施例57的化合物40%(w/w)、乳糖60%(w/w)。
制剂例5.气溶胶剂
制备气溶胶剂,达到含有实施例57的化合物10%(w/w)、卵磷脂0.5%(w/w)、フロン11为34.5%(w/w)、フロン12为55%(w/w)。
发明效果
由于本发明通式(I)所示化合物、其药理上可接受的醚或酯衍生物及其药理上可接受的盐,对于各种细菌(优选抗酸菌、特别优选结核菌)显示优秀的抗菌力,因此,它们作为细菌引起的感染症的预防药或治疗药(优选治疗药)是有用的。

Claims (58)

1、通式(I)所示化合物、其药理上可接受的酯、醚或N-烷基衍生物、或其药理上可接受的盐:
Figure A0081465300021
式中
X1表示氧原子、硫原子或式-N(R4)-所示基团,式中,R4表示氢原子,碳原子数1~3的烷基,或与R1以及与它们连接的氮原子一起形成可含有氧原子或硫原子的3~7元环状氨基的基团,
X2表示氧原子、硫原子或式-N(R5)-所示基团,式中,R5表示氢原子,碳原子数1~3的烷基,或与R2以及与它们连接的氮原子一起形成可含有氧原子或硫原子的3~7元环状氨基的基团,
R1和R2可相同或不同,表示
(1)氢原子,
(2)可具有取代基的碳原子数6~10的芳基所述取代基表示选自由卤原子,羟基,氨基,所述氨基可被碳原子数1~16的烷基取代,硝基,氰基,羧基,碳原子数1~4的烷氧羰基,氨基甲酰基,碳原子数1~10的亚烷基二氧基,碳原子数7~14的芳烷氧基,碳原子数1~16的烷基,所述烷基可被卤原子取代,碳原子数2~16的链烯基,碳原子数1~16的烷氧基,所述烷氧基可被卤原子取代,碳原子数1~16的烷硫基,所述烷硫基可被卤原子取代,碳原子数6~10的芳基偶氮基,和含有1~4个氮原子、硫原子或氧原子的杂环基组成的取代基组A的基团,
(3)可具有取代基的含有1~4个氮原子、硫原子或氧原子的杂环基所述取代基表示选自由氧代基,硫代氧代基,亚氨基,卤原子,羟基,氨基,所述氨基可被碳原子数1~16的烷基取代,硝基,氰基,羧基,碳原子1~4的烷氧羰基,氨基甲酰基,碳原子数7~14的芳烷氧基,碳原子数1~16的烷基,所述烷基可被卤原子取代,碳原子数1~16的链烯基,碳原子数1~16的烷氧基,所述烷氧基可被卤原子取代,和可被卤原子取代的碳原子数1~16的烷硫基组成的取代基组B的基团,
(4)具有1~3个相同或不同的可具有取代基的碳原子数6~10的芳基取代基的碳原子数1~14的烷基所述芳基部分的取代基表示选自上述取代基组A的基团,
(5)具有1~3个相同或不同的可具有取代基的含有1~4个氮原子、硫原子或氧原子的杂环基取代基的碳原子数1~14的烷基所述杂环基部分的取代基表示选自上述取代基组B的基团,
(6)可具有取代基的碳原子数1~22的烷基所述取代基表示选自由卤原子,羟基,氨基,硝基,氰基,羧基,碳原子1~4的烷氧羰基,氨基甲酰基,碳原子数1~16的烷氧基,所述烷氧基可被卤原子取代,和可被卤原子取代的碳原子数1~16的烷硫基组成的取代基组C的基团,
(7)可具有取代基的碳原子数2~22的链烯基所述取代基表示选自上述(2)或(3)的基团或选自取代基组C的基团,或
(8)式(a)所示基团
Figure A0081465300031
式中,n表示1~20的整数,m表示0或2,
R3表示氢原子或羟基,
条件是,其中X1和X2是式-NH-所示基团,R1是氢原子或式(II)、(III)、(IV)或(V)所示基团,R2是氢原子,R3是羟基的化合物,以及其中X1是氧原子,X2是式-NH-所示基团,R1是氢原子或甲基,R2是氢原子,R3是羟基的化合物除外。
2、权利要求1的化合物、其药理上可接受的酯、醚或N-烷基衍生物或其药理上可接受的盐,其中,X1是式-N(R4)-表示的基团。
3、权利要求1的化合物、其药理上可接受的酯、醚或N-烷基衍生物或其药理上可接受的盐,其中,X1是式-N(R4)-表示的基团,式中R4表示氢原子或碳原子数1~3的烷基。
4、权利要求1的化合物、其药理上可接受的酯、醚或N-烷基衍生物或其药理上可接受的盐,其中,X1是式-NH-表示的基团。
5、权利要求1~4中任一项的化合物、其药理上可接受的酯、醚或N-烷基衍生物或其药理上可接受的盐,其中,X2是式-N(R5)-表示的基团。
6、权利要求1~4任一项的化合物、其药理上可接受的酯、醚或N-烷基衍生物或其药理上可接受的盐,其中,X2是式-N(R5)-所示基团,式中R5表示氢原子或碳原子数1~3的烷基。
7、权利要求1~4任一项的化合物、其药理上可接受的酯、醚或N-烷基衍生物或其药理上可接受的盐,其中,X2是式-NH-所示基团。
8、权利要求1~7任一项的化合物、其药理上可接受的酯、醚或N-烷基衍生物或其药理上可接受的盐,其中R1是氢原子。
9、权利要求1~7任一项的化合物、其药理上可接受的酯、醚或N-烷基衍生物或其药理上可接受的盐,其中,R1是可具有取代基的碳原子数6~10的芳基,所述取代基表示选自取代基组A的基团。
10、权利要求9的化合物、其药理上可接受的酯、醚或N-烷基衍生物或其药理上可接受的盐,其中R1是可具有取代基的苯基、1-萘基或2-萘基,所述取代基表示选自取代基组A的基团。
11、权利要求9的化合物、其药理上可接受的酯、醚或N-烷基衍生物或其药理上可接受的盐,其中,R1是可具有取代基的苯基,所述取代基表示选自取代基组A的基团。
12、权利要求1~7任一项的化合物、其药理上可接受的酯、醚或N-烷基衍生物或其药理上可接受的盐,其中,R1是可具有取代基的含有1~4个氮原子、硫原子或氧原子的杂环基,所述取代基表示选自取代基组B的基团。
13、权利要求12的化合物、其药理上可接受的酯、醚或N-烷基衍生物或其药理上可接受的盐,其中,R1是可具有取代基的5元或6元芳族杂环基或与苯环稠合的5元或6元芳族杂环基,所述取代基表示选自取代基组B的基团。
14、权利要求1~7任一项的化合物、其药理上可接受的酯、醚或N-烷基衍生物或其药理上可接受的盐,其中,R1是具有1~3个相同或不同的可具有取代基的碳原子数6~10的芳基取代基的碳原子数1~14的烷基,所述取代基表示选自取代基组A的基团。
15、权利要求14的化合物、其药理上可接受的酯、醚或N-烷基衍生物或其药理上可接受的盐,其中,R1的芳基部分是可具有取代基的苯基、1-萘基或2-萘基,所述取代基表示选自取代基组A的基团。
16、权利要求14的化合物、其药理上可接受的酯、醚或N-烷基衍生物或其药理上可接受的盐,其中R1的芳基部分是可具有取代基的苯基,所述取代基表示选自取代基组A的基团。
17、权利要求14~16任一项的化合物、其药理上可接受的酯、醚或N-烷基衍生物或其药理上可接受的盐,其中,R1的烷基部分是碳原子数1~8的烷基。
18、权利要求14~16任一项的化合物、其药理上可接受的酯、醚或N-烷基衍生物或其药理上可接受的盐,其中,R1的烷基部分是碳原子数1~4的烷基。
19、权利要求14~16任一项的化合物、其药理上可接受的酯、醚或N-烷基衍生物或其药理上可接受的盐,其中,R1的烷基部分是碳原子数为2的烷基。
20、权利要求1~7任一项的化合物、其药理上可接受的酯、醚或N-烷基衍生物或其药理上可接受的盐,其中,R1是具有1~3个相同或不同的可具有取代基的含有1~4个氮原子、硫原子或氧原子的杂环基取代基的碳原子数1~14的烷基,所述取代基表示选自取代基组B的基团。
21、权利要求20的化合物、其药理上可接受的酯、醚或N-烷基衍生物或其药理上可接受的盐,其中,R1的杂环部分是可具有取代基的5或6元芳族杂环基或与苯环稠合的5元或6元芳族杂环基,所述取代基表示选自取代基组B的基团。
22、权利要求20或21任一项的化合物、其药理上可接受的酯、醚或N-烷基衍生物或其药理上可接受的盐,其中,R1的烷基部分是碳原子数1~8的烷基。
23、权利要求20或21任一项的化合物、其药理上可接受的酯、醚或N-烷基衍生物或其药理上可接受的盐,其中,R1的烷基部分是碳原子数1~4的烷基。
24、权利要求20或21任一项的化合物、其药理上可接受的酯、醚或N-烷基衍生物或其药理上可接受的盐,其中,R1的烷基部分是碳原子数为2的烷基。
25、权利要求1~7任一项的化合物、其药理上可接受的酯、醚或N-烷基衍生物或其药理上可接受的盐,其中,R1是可具有取代基的碳原子数1~22的烷基,所述取代基表示选自取代基组C的基团。
26、权利要求25的化合物、其药理上可接受的酯、醚或N-烷基衍生物或其药理上可接受的盐,其中,R1是可具有取代基的碳原子数1~18的烷基,所述取代基表示选自取代基组C的基团。
27、权利要求1~7任一项的化合物、其药理上可接受的酯、醚或N-烷基衍生物或其药理上可接受的盐,其中,R1是可具有取代基的碳原子数2~22的链烯基,所述取代基表示选自权利要求1中的R1定义中的(2)或(3)的基团或选自取代基组C的基团。
28、权利要求27的化合物、其药理上可接受的酯、醚或N-烷基衍生物或其药理上可接受的盐,其中,R1是未取代的碳原子数2~22的链烯基。
29、权利要求27的化合物、其药理上可接受的酯、醚或N-烷基衍生物或其药理上可接受的盐,其中,R1是未取代的碳原子数2~18的链烯基。
30、权利要求1的化合物、其药理上可接受的酯、醚或N-烷基衍生物或其药理上可接受的盐,其中,R1是式(a)所示基团,式中,n表示1~20的整数,m表示0或2。
31、权利要求30的化合物、其药理上可接受的酯、醚或N-烷基衍生物或其药理上可接受的盐,其中,n是4~8的整数。
32、权利要求30的化合物、其药理上可接受的酯、醚或N-烷基衍生物或其药理上可接受的盐,其中,m是0,n是4~8的整数。
33、权利要求1~32任一项的化合物、其药理上可接受的酯、醚或N-烷基衍生物或其药理上可接受的盐,其中,R2是氢原子、可具有选自取代基组C的基团的取代基的碳原子数1~22的烷基或可具有选自取代基组C的基团的取代基的碳原子数2~22的链烯基。
34、权利要求1~32任一项的化合物、其药理上可接受的酯、醚或N-烷基衍生物或其药理上可接受的盐,其中,R2是氢原子、未取代的碳原子数1~22的烷基或未取代的碳原子数2~22的链烯基。
35、权利要求1~32任一项的化合物、其药理上可接受的酯、醚或N-烷基衍生物或其药理上可接受的盐,其中,R2是氢原子、未取代的碳原子数6~20的烷基或未取代的碳原子数10~20的链烯基。
36、权利要求1~32任一项的化合物、其药理上可接受的酯、醚或N-烷基衍生物或其药理上可接受的盐,其中,R2是氢原子或未取代的碳原子数6~20的烷基。
37、权利要求1~32任一项的化合物、其药理上可接受的酯、醚或N-烷基衍生物或其药理上可接受的盐,其中,R2是氢原子。
38、权利要求1~37任一项的化合物、其药理上可接受的酯、醚或N-烷基衍生物或其药理上可接受的盐,其中,R3是羟基。
39、权利要求1的化合物、其药理上可接受的酯、醚或N-烷基衍生物或其药理上可接受的盐,其中,
X1是式-N(R4)-所示基团,
X2是式-N(R5)-所示基团,
R1是(2)可具有取代基的碳原子数6~10的芳基,所述取代基表示选自取代基组A的基团,(4)具有1~3个相同或不同的可具有取代基的碳原子数6~10的芳基取代基的碳原子数1~14的烷基,所述取代基表示选自取代基组A的基团,(5)具有1~3个相同或不同的可具有取代基的含有1~4个氮原子、硫原子或氧原子的杂环基取代基的碳原子数1~14的烷基,所述取代基表示选自取代基组B的基团,(6)可具有取代基的碳原子数1~22的烷基,所述取代基表示选自取代基组C的基团,(7)可具有取代基的碳原子数2~22的链烯基,所述取代基表示选自权利要求1中的R1定义中的(2)或(3)的基团或选自取代基组C的基团,或(8)式(a)所示基团,
R2是氢原子或未取代的碳原子数6~20的烷基,
R3是氢原子或羟基。
40、权利要求1的化合物、其药理上可接受的酯、醚或N-烷基衍生物或其药理上可接受的盐,其中,
X1和X2是式-NH-所示基团,
R1是(2)可具有取代基的碳原子数6~10的芳基,所述取代基表示选自取代基组A的基团,(4)具有1~3个相同或不同的可具有取代基的碳原子数6~10的芳基取代基的碳原子数1~14的烷基,所述取代基表示选自取代基组A的基团,(5)具有1~3个相同或不同的可具有取代基的含有1~4个氮原子、硫原子或氧原子的杂环基取代基的碳原子数1~14的烷基,所述取代基表示选自取代基组B的基团,(6)可具有取代基的碳原子数1~22的烷基,所述取代基表示选自取代基组C的基团,(7)可具有取代基的碳原子数2~22的链烯基,所述取代基表示选自权利要求1中的R1定义中的(2)或(3)中的基团或选自取代基组C的基团,或(8)式(a)所示基团,
R2是氢原子或未取代的碳原子数6~20的烷基,
R3是氢原子或羟基。
41、权利要求1的化合物、其药理上可接受的酯、醚或N-烷基衍生物或其药理上可接受的盐,其中,
X1和X2是式-NH-所示基团,
R1是(2)可具有取代基的碳原子数6~10的芳基,所述取代基表示选自取代基组A的基团,(6)可具有取代基的碳原子数1~22的烷基,所述取代基表示选自取代基组C的基团,或(7)可具有取代基的碳原子数2~22的链烯基,所述取代基表示选自取代基组C的基团,
R2是氢原子或未取代的碳原子数6~20的烷基,
R3是氢原子或羟基。
42、权利要求1的化合物、其药理上可接受的酯、醚或N-烷基衍生物或其药理上可接受的盐,其中,
X1和X2是式-NH-所示基团,
R1是(2)可具有取代基的碳原子数6~10的芳基,所述取代基表示选自取代基组A的基团或(6)可具有取代基的碳原子数1~22的烷基,所述取代基表示选自取代基组C的基团,
R2是氢原子或未取代的碳原子数6~20的烷基,
R3是氢原子或羟基。
43、权利要求1的化合物、其药理上可接受的酯、醚或N-烷基衍生物或其药理上可接受的盐,其中,
X1和X2是式-NH-所示基团,
R1是(2)可具有取代基的碳原子数6~10的芳基,所述取代基表示选自取代基组A的基团,
R2是氢原子或未取代的碳原子数6~20的烷基,
R3是氢原子或羟基。
44、权利要求1的化合物、其药理上可接受的酯、醚或N-烷基衍生物或其药理上可接受的盐,其中,
X1和X2是式-NH-所示基团,
R1是可具有取代基的苯基,所述取代基表示选自取代基组A的基团,
R2是氢原子,且
R3是羟基。
45、权利要求1的化合物、其药理上可接受的酯、醚或N-烷基衍生物或其药理上可接受的盐,其中,
X1和X2是式-NH-所示基团,
R1是可具有取代基的苯基,所述取代基表示选自取代基组A的基团,
R2是未取代的碳原子数6~20的烷基,且
R3是羟基。
46、权利要求1的化合物、其药理上可接受的酯、醚或N-烷基衍生物或其药理上可接受的盐,其中,
X1和X2是式-NH-所示基团,
R1是可具有取代基的苯基,所述取代基表示选自取代基组A的基团,且
R2和R3是氢原子。
47、权利要求1~46任一项的化合物、其药理上可接受的酯、醚或N-烷基衍生物或其药理上可接受的盐,其中,通式(I)是通式(I’)
Figure A0081465300101
式中,R1、R2、R3、X1和X2与权利要求1-46任一项中的定义相同。
48、权利要求4 7的通式(I’)所示化合物、其药理上可接受的酯、醚或N-烷基衍生物,其中化合物选自下列的化合物或其药理上可接受的盐:
R1表示苯基、R2表示氢原子、X1和X2表示式-NH-所示基团、R3表示羟基的化合物、
R1表示苯基、R2表示氢原子、X1和X2表示式-NH-所示基团、R3表示癸酰氧基的化合物、
R1表示4-乙基苯基、R2表示氢原子、X1和X2表示式-NH-所示基团、R3表示羟基的化合物、
R1表示4-乙基苯基、R2表示氢原子、X1和X2表示式-NH-所示基团、R3表示癸酰氧基的化合物、
R1表示4-戊基苯基、R2表示氢原子、X1和X2表示式-NH-所示基团、R3表示羟基的化合物、
R1表示3-乙基苯基、R2表示氢原子、X1和X2表示式-NH-所示基团、R3表示羟基的化合物、
R1表示4-三氟甲基苯基、R2表示氢原子、X1和X2表示式-NH-所示基团、R3表示羟基的化合物、
R1表示4-三氟甲基苯基、R2表示氢原子、X1和X2表示式-NH-所示基团、R3表示癸酰氧基的化合物、
R1表示4-丁氧苯基、R2表示氢原子、X1和X2表示式-NH-所示基团、R3表示羟基的化合物、
R1表示4-戊氧苯基、R2表示氢原子、X1和X2表示式-NH-所示基团、R3表示羟基的化合物、
R1表示4-己氧苯基、R2表示氢原子、X1和X2表示式-NH-所示基团、R3表示羟基的化合物、
R1表示4-氟苯基、R2表示氢原子、X1和X2表示式-NH-所示基团、R3表示羟基的化合物、
R1表示4-氟苯基、R2表示氢原子、X1和X2表示式-NH-所示基团、R3表示癸酰氧基的化合物、
R1表示3,4-二氟苯基、R2表示氢原子、X1和X2表示式-NH-所示基团、R3表示羟基的化合物、
R1表示3,4-二氟苯基、R2表示氢原子、X1和X2表示式-NH-所示基团、R3表示癸酰氧基的化合物、
R1表示3-氯-4-氟苯基、R2表示氢原子、X1和X2表示式-NH-所示基团、R3表示羟基的化合物、
R1表示3-氯-4-氟苯基、R2表示氢原子、X1和X2表示式-NH-所示基团、R3表示癸酰氧基的化合物、
R1表示3-三氟甲基-4-氟苯基、R2表示氢原子、X1和X2表示式-NH-所示基团、R3表示羟基的化合物、
R1表示3-三氟甲基-4-氟苯基、R2表示氢原子、X1和X2表示式-NH-所示基团、R3表示癸酰氧基的化合物、
R1表示3-甲基-4-溴苯基、R2表示氢原子、X1和X2表示式-NH-所示基团、R3表示羟基的化合物、
R1表示3-甲基-4-溴苯基、R2表示氢原子、X1和X2表示式-NH-所示基团、R3表示癸酰氧基的化合物、
R1表示3-硝基-4-氟苯基、R2表示氢原子、X1和X2表示式-NH-所示基团、R3表示羟基的化合物、
R1表示3-硝基-4-氟苯基、R2表示氢原子、X1和X2表示式-NH-所示基团、R3表示癸酰氧基的化合物、
R1表示3-硝基苯基、R2表示氢原子、X1和X2表示式-NH-所示基团、R3表示羟基的化合物、以及
R1表示3-硝基苯基、R2表示氢原子、X1和X2表示式-NH-所示基团、R3表示癸酰氧基的化合物。
49、含有权利要求1~48任一项中记载的化合物(I)或(I’)、其药理上可接受的酯、醚或N-烷基衍生物或其药理上可接受的盐作为有效成分的药物。
50、含有权利要求1~48任一项中记载的化合物(I)或(I’)、其药理上可接受的酯、醚或N-烷基衍生物或其药理上可接受的盐作为有效成分的用于预防或治疗细菌感染症的组合物。
51、含有权利要求1~48任一项中记载的化合物(I)或(I’)、其药理上可接受的酯、醚或N-烷基衍生物或其药理上可接受的盐作为有效成分的用于预防或治疗抗酸菌感染症的组合物。
52、含有权利要求1~48任一项中记载的化合物(I)或(I’)、其药理上可接受的酯、醚或N-烷基衍生物或其药理上可接受的盐作为有效成分的用于预防或治疗结核菌感染症的组合物。
53、权利要求1~48任一项中记载的化合物(I)或(I’)、其药理上可接受的酯、醚或N-烷基衍生物或其药理上可接受的盐在用于预防或治疗细菌感染症的药物制备中的应用。
54、权利要求1~48任一项中记载的化合物(I)或(I’)、其药理上可接受的酯、醚或N-烷基衍生物或其药理上可接受的盐在用于预防或治疗抗酸菌感染症的药物制备中的应用。
55、权利要求1~48任一项中记载的化合物(I)或(I’)、其药理上可接受的酯、醚或N-烷基衍生物或其药理上可接受的盐在用于预防或治疗结核菌感染症的药物制备中的应用。
56、预防或治疗细菌感染症的方法,是使用药理有效量的权利要求1~48任一项中记载的化合物(I)或(I’)、其药理上可接受的酯、醚或N-烷基衍生物或其药理上可接受的盐对温血动物给药。
57、预防或治疗抗酸菌感染症的方法,是使用药理有效量的权利要求1~48任一项中记载的化合物(I)或(I’)、其药理上可接受的酯、醚或N-烷基衍生物或其药理上可接受的盐对温血动物给药。
58、预防或治疗结核菌感染症的方法,是使用药理有效量的权利要求1~48任一项中记载的化合物(I)或(I’)、其药理上可接受的酯、醚或N-烷基衍生物或其药理上可接受的盐对温血动物给药。
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Families Citing this family (9)

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Publication number Priority date Publication date Assignee Title
HUP0103711A3 (en) * 1998-07-09 2003-11-28 Sankyo Company Ltd Chuo Ku Novel antimicrobial compounds
US20040033986A1 (en) * 2002-05-17 2004-02-19 Protopopova Marina Nikolaevna Anti tubercular drug: compositions and methods
US7456222B2 (en) * 2002-05-17 2008-11-25 Sequella, Inc. Anti tubercular drug: compositions and methods
CN101404986B (zh) * 2002-05-17 2011-09-28 赛奎拉公司 用于诊断和治疗感染性疾病的组合物和制药方法
WO2005034857A2 (en) * 2003-09-05 2005-04-21 Sequella, Inc. Methods and compositions comprising diamines as new anti-tubercular therapeutics
US20090281054A1 (en) * 2008-05-06 2009-11-12 Venkata Reddy Compositions and methods comprising capuramycin analogues
KR101104505B1 (ko) * 2010-01-30 2012-01-12 김근섭 호스 연결용 원클릭 피팅
WO2015027137A1 (en) * 2013-08-23 2015-02-26 University Of Tennessee Research Foundation Improved synthesis of capuramycin and its analogues
US20230340006A1 (en) * 2020-06-30 2023-10-26 University Of Tennessee Research Foundation Dpagt1 inhibitors of capuramycin analogues and their antimigratory activities of solid tumors

Family Cites Families (10)

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Publication number Priority date Publication date Assignee Title
JPS60259190A (ja) * 1984-06-06 1985-12-21 Kanto Ishi Pharma Co Ltd 新抗生物質カプラマイシン及びその製造法
US5034381A (en) 1988-01-07 1991-07-23 Ciba-Geigy Corporation 2-(substituted amino) adenosines as antihypertensives
JPH05148293A (ja) * 1991-11-28 1993-06-15 Mect Corp 新規カプラマイシン誘導体およびその製造方法
GB9307043D0 (en) 1993-04-05 1993-05-26 Norsk Hydro As Chemical compounds
HUP0103711A3 (en) 1998-07-09 2003-11-28 Sankyo Company Ltd Chuo Ku Novel antimicrobial compounds
JP4428762B2 (ja) 1998-07-09 2010-03-10 セケラ インコーポレイテッド 抗生物質a−500359及び誘導体
JP2000072774A (ja) * 1998-08-25 2000-03-07 Sankyo Co Ltd ラクトン誘導体
JP4531167B2 (ja) 1998-09-24 2010-08-25 セケラ インコーポレイテッド 新規抗細菌化合物
JP5022539B2 (ja) 2000-01-07 2012-09-12 セケラ インコーポレイテッド 抗生物質a−500359及び誘導体を含有する抗菌剤
JP4960548B2 (ja) * 2000-01-07 2012-06-27 セケラ インコーポレイテッド 新規抗細菌化合物の用途

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US20030171330A1 (en) 2003-09-11
NZ517315A (en) 2004-02-27
HUP0204217A2 (en) 2003-03-28
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RU2227799C2 (ru) 2004-04-27
BR0013435A (pt) 2002-07-16
NO323556B1 (no) 2007-06-11
PT1209166E (pt) 2004-06-30
KR100787849B1 (ko) 2007-12-27
ZA200201409B (en) 2003-07-30
HK1044951A1 (zh) 2002-11-08
IL148196A (en) 2008-06-05
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WO2001014399A1 (fr) 2001-03-01
ES2216933T3 (es) 2004-11-01
CA2382654C (en) 2009-01-13
CZ2002682A3 (cs) 2002-06-12
NO20020804L (no) 2002-04-19
PL353494A1 (en) 2003-11-17
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