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MD4519B1 - Use of (Z)-4,4-dimethyl-1-(4-nitrophenyl)-2-(1H-1,2,4-triazol-1-yl)pent-1-en-3-one as antituberculous agent - Google Patents

Use of (Z)-4,4-dimethyl-1-(4-nitrophenyl)-2-(1H-1,2,4-triazol-1-yl)pent-1-en-3-one as antituberculous agent Download PDF

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Publication number
MD4519B1
MD4519B1 MDA20170068A MD20170068A MD4519B1 MD 4519 B1 MD4519 B1 MD 4519B1 MD A20170068 A MDA20170068 A MD A20170068A MD 20170068 A MD20170068 A MD 20170068A MD 4519 B1 MD4519 B1 MD 4519B1
Authority
MD
Moldova
Prior art keywords
triazol
dimethyl
pent
nitrophenyl
antituberculous
Prior art date
Application number
MDA20170068A
Other languages
Romanian (ro)
Russian (ru)
Other versions
MD4519C1 (en
Inventor
Флюр МАКАЕВ
Марина ЗВЯГИНЦЕВА
Еуджения СТЫНГАЧ
Сергей ПОГРЕБНОЙ
Георге ДУКА
Original Assignee
Институт Химии Академии Наук Молдовы
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Институт Химии Академии Наук Молдовы filed Critical Институт Химии Академии Наук Молдовы
Priority to MDA20170068A priority Critical patent/MD4519C1/en
Publication of MD4519B1 publication Critical patent/MD4519B1/en
Publication of MD4519C1 publication Critical patent/MD4519C1/en

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Abstract

The invention relates to pharmaceutical chemistry and can be used in the development of new agents for the treatment of tuberculosis of the 1,2,4-triazole class.Summary of the invention consists in that it is proposed as antituberculous agent the (Z)-4,4-dimethyl-1-(4-nitrophenyl)-2-(1H-1,2,4-triazol-1-yl)pent-1-en-3-one with the formula:.The compound exhibits antituberculous activity against Mycobacterium tuberculosisH37Rv (ATCC 27294) comparable to rifampicin.The isomeric compound is obtained by selective aldol-crotonic condensation of 3,3-dimethyl-1-(1H-1,2,4-triazol-1-yl)butan-2-one with 4-nitrobenzaldehyde, which occurs during reflux in benzene, with azeotropic distillation of the formed water, in the presence of a piperidine-acetic acid catalyst (70%, m.p. 114…116°C).
MDA20170068A 2016-12-21 2016-12-21 Use of (Z)-4,4-dimethyl-1-(4-nitrophenyl)-2-(1H-1,2,4-triazol-1-yl)pent-1-en-3-one as antituberculous agent MD4519C1 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
MDA20170068A MD4519C1 (en) 2016-12-21 2016-12-21 Use of (Z)-4,4-dimethyl-1-(4-nitrophenyl)-2-(1H-1,2,4-triazol-1-yl)pent-1-en-3-one as antituberculous agent

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
MDA20170068A MD4519C1 (en) 2016-12-21 2016-12-21 Use of (Z)-4,4-dimethyl-1-(4-nitrophenyl)-2-(1H-1,2,4-triazol-1-yl)pent-1-en-3-one as antituberculous agent

Publications (2)

Publication Number Publication Date
MD4519B1 true MD4519B1 (en) 2017-10-31
MD4519C1 MD4519C1 (en) 2018-05-31

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MDA20170068A MD4519C1 (en) 2016-12-21 2016-12-21 Use of (Z)-4,4-dimethyl-1-(4-nitrophenyl)-2-(1H-1,2,4-triazol-1-yl)pent-1-en-3-one as antituberculous agent

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Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CA1168248A (en) * 1980-07-25 1984-05-29 Erik Regel Triazolylpropenol derivatives, a process for their preparation and their use as plant growth regulators and fungicides
US4749716A (en) * 1979-03-20 1988-06-07 Sumitomo Chemical Company, Limited Geometrical isomer of 1-substituted-1-triazolystyrenes

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4749716A (en) * 1979-03-20 1988-06-07 Sumitomo Chemical Company, Limited Geometrical isomer of 1-substituted-1-triazolystyrenes
CA1168248A (en) * 1980-07-25 1984-05-29 Erik Regel Triazolylpropenol derivatives, a process for their preparation and their use as plant growth regulators and fungicides

Non-Patent Citations (4)

* Cited by examiner, † Cited by third party
Title
Funaki Y., Ishiguri Y., Kato T. and Tanaka S. Structure-Activity Relationships of Vinyl Triazole Fungicide. J. Pesticide Sci. 9, 229-236 (1984). regăsit în Internet la 2017.06.08, url: https://www.jstage.jst.go.jp/article/jpestics1975/9/2/9_2_229/_pdf Pages 229, 230; Table 1, compounds 7 and 15 *
Pawan Kumar Mishra, Jaya Dwivedi, Rajani Chauhan. Triazoles as potential antitubercular agent: a review. Journal of Advanced Scientific Research, 2016, 7(1), 9-13 *
R. Singh and A. Chouhan. IMPORTANT METHODS OF SYNTHESIS AND BIOLOGICAL SIGNIFICANCE OD 1,2,4-TRIAZOLES DERIVATIVES. WORLD JOURNAL OF PHARMACY AND PHARMACEUTICAL SCIENCES, Vol. 3, Issue 8, 874-906, 2014. Regăsit îm Internet la 2017.08.01, url: http://www.wjpps.com/download/article/1406694109.pdf pag. 894-895, Antitubercular activity *
Rangappa S. Keri, Siddappa A. Patil, Srinivasa Budagumpi, Bhari Mallanna Nagaraja. Triazole: A Promising Antitubercular Agent. Chem Biol Drug Des 2015, 86, 410-423. Regăsit în Internet la 2017.07.31, url: http://www.sciensage.info/journal/1457099361JASR_2409151.pdf *

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Publication number Publication date
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FG4A Patent for invention issued
KA4A Patent for invention lapsed due to non-payment of fees (with right of restoration)
MM4A Patent for invention definitely lapsed due to non-payment of fees