CN118909162A - Silicon-based resin compound and preparation method and application thereof - Google Patents

Abstract

The invention provides a silicon-based resin compound, which has a structure shown as a formula (I): The invention also provides a preparation method of the silicon-based resin compound, which comprises the following steps: s1: taking a first compound containing P resin, and carrying out substitution reaction to obtain a second compound; s2: the second compound is subjected to at least one addition and/or substitution addition reaction to obtain a third compound; s3: and carrying out catalytic coupling reaction on the third compound and aryl halide to obtain the silicon-based resin compound. The invention also provides application of the silicon-based resin compound in radiolabeling. The silicon-based resin compound and the application thereof can obviously improve the radiochemical yield of the radioactive iodine/astatine label, reduce the occurrence of side reaction, simplify the subsequent separation and purification steps and directly obtain the high-purity labeled product.

Description

A silicon-based resin compound and its preparation method and application

Technical Field

The present invention relates to the field of silicon-based resin compounds, and in particular to a silicon-based resin compound and a preparation method and application thereof.

Background Art

Radioactive labeling technology has important applications in nuclear medicine imaging, radioactive tracer research, and targeted tumor therapy. These technologies use radioactive isotopes (such as iodine-123, iodine-124, iodine-125, iodine-131, and astatine-211) to label specific drugs or biomolecules so that lesions can be clearly displayed in medical imaging or directly act on tumor cells during treatment. However, existing radioactive iodine/astatine labeling methods have some limitations. The reaction method itself has problems such as harsh reaction conditions, low radiochemical yield, many side reactions, and time-consuming high-performance liquid chromatography separation. In terms of application, there are problems such as a narrow scope of application and in vivo deiodination.

The main products and methods of existing radioactive iodine/astatine labeling technology include:

Direct labeling method: Direct labeling method of iodine is a more commonly used radioactive iodine labeling method. The labeling principle is shown as follows:

The labeling process mainly involves an electrophilic substitution reaction, in which *I- undergoes an oxidation reaction under the action of an oxidant to generate *I ₂ or *I ⁺ , and then electrophilically replaces hydrogen atoms on specific groups of aromatic compounds in target molecules or drugs (such as tyrosine, phenylalanine, tryptophan and histidine contained in proteins and polypeptides, benzene rings, phenol rings and other active rings). The direct labeling method has the advantages of high radiochemical yield, simple operation, and cheap reagents. However, the raw material used in this method is a strong oxidant, which may cause damage to sensitive labeled substances (such as receptors and hormones with unstable biological activity), such as the breakage of tryptophan peptide bonds, oxidation of thiol or thioether groups in the structure, resulting in loss of biological activity of the labeled substance, etc.

Indirect labeling method: Compared with the direct labeling method of directly coupling the object to be labeled with the radioactive nuclide, the indirect labeling method is mostly through the intermediate or precursor material first combined with the drug or biological molecule, and then labeled with radioactive iodine. It requires at least two steps of reaction to obtain a marker with the structure of "radioactive nuclide + auxiliary group + targeting molecule or drug". The labeling principle is shown in the following formula.

Although this method can alleviate the extreme reaction conditions of the direct labeling method to a certain extent, it still has problems such as harsh reaction conditions, low radiochemical yield, and many side reactions. Although the indirect radioiodine labeling method can broaden the range of molecules to be labeled and improve the stability of the labeled product to a certain extent, its labeling process requires multiple reactions, and the radiochemical yield is an issue that needs to be considered. In addition, the conventional method for preparing radiolabeled compounds is costly and the steps are cumbersome.

Summary of the invention

The first technical problem to be solved by the present invention is to provide a silicon-based resin compound to solve the problems of harsh reaction conditions, low radiochemical yield, many side reactions and easy damage to the labeled substance in conventional radioactive labeling.

In order to solve the above technical problems, the present invention provides a silicon-based resin compound, wherein the silicon-based resin compound has a structure as shown in formula (I):

Wherein, P is a resin, and the resin is one of Wang resin, chloromethyl polystyrene resin, and polyethylene glycol resin; X is one of -CH ₂ CH ₂ CH ₂ -, -O(CH ₂ CH ₂ OCH ₂ CH ₂ ) _n CH ₂ CH ₂ -, and -O(CH ₂ CH ₂ OCH ₂ CH ₂ ) _n CH ₂ CH ₂ O-; Y is one of -Me, -Et, -CH(CH ₃ ) ₂ , and -C(CH ₃ ) ₃ ; and Ar is an aromatic hydrocarbon group.

Compared with the prior art, the silicone-based resin compound in the present invention has the following advantages:

1) The silicon-based resin compound of the present invention has a highly efficient radioactive iodine/astatine binding ability, ensuring the completeness and stability of the labeling reaction;

2) The silicon-based resin compound of the present invention has excellent chemical stability and biocompatibility and is suitable for labeling a variety of drug molecules;

3) The silicone-based resin compound of the present invention has the advantages of simple operation and mild conditions in practical application, and is suitable for laboratory and industrial production.

In one possible embodiment, the aromatic hydrocarbon group is

One of them.

In a possible implementation, the degree of polymerization of the silicon-based resin compound is less than 4000.

The second technical problem to be solved by the present invention is to provide a method for preparing a silicone-based resin compound to solve the problem that the conventional preparation method has complicated steps and high costs.

In order to solve the above technical problems, the present invention provides a method for preparing the silicone-based resin compound, the preparation method comprising:

S1: taking a first compound containing a P resin and subjecting it to a substitution reaction to obtain a second compound;

S2: subjecting the second compound to at least one addition and/or substitution addition reaction to obtain a third compound;

S3: subjecting the third compound to a catalytic coupling reaction with an aromatic halide to obtain a silicon-based resin compound.

The above-mentioned preparation method of the present invention provides a preparation method of silicone-based resin compounds without complicated steps and simple operation, which overcomes the problems of high cost and complicated steps of radioactive labeled compounds in the prior art.

In a possible embodiment, the first compound is chloromethyl polystyrene resin, and the preparation method comprises:

S1: Resin a and magnesium chloride are reacted by substitution to obtain compound b;

S2: Compound b reacts with silane to obtain compound c;

S3: Compound c and an aromatic halide are subjected to a catalytic coupling reaction to obtain a silicon-based resin compound d, which is the silicon-based resin compound;

The reaction process of the preparation method is as follows:

In the formula, Z is one of Cl, Br, and I, a is resin a, b is compound b, c is compound c, and d is silicon-based resin compound d.

In a possible embodiment, the first compound is Wang resin, and the preparation method comprises:

S1: Resin e and triphenylphosphine bromide undergo substitution reaction to obtain compound f;

S2: Compound f is reacted with magnesium chloride to obtain compound g through substitution addition reaction, and compound g is reacted with dialkylsilane to obtain compound h through addition reaction;

S3: Compound h and aryl halide undergo catalytic coupling reaction to obtain silicone-based resin compound i;

The reaction process of the preparation method is as follows:

In the formula, Z is one of Cl, Br, and I, e is resin e, f is reactant f, g is compound g, h is compound h, and i is silicon-based resin compound i.

In a possible embodiment, the first compound is Wang resin or chloromethyl polystyrene resin, and the preparation method comprises:

S1: Resin j and polyethylene glycol undergo substitution reaction to obtain compound k;

S2: Compound k is reacted with thionyl chloride to obtain compound l through substitution and addition reaction; compound l is reacted with magnesium chloride to obtain compound m through substitution reaction; compound m is reacted with dialkylsilane to obtain compound n through addition reaction;

S3: Compound n is reacted with an aromatic halide by catalytic coupling reaction to obtain a silicon-based resin compound o; wherein n<4000, is a resin selected from: Wang resin, chloromethyl polystyrene resin, Z is selected from: Cl, Br, I, Y refers to the same as described in claim 1, and Ar refers to the same as described in claim 1;

The reaction process of the preparation method is as follows:

In the formula, Z is one of Cl, Br, and I, j is resin j, k is compound k, l is compound l, m is compound m, n is compound n, and o is silicone-based resin compound o.

In a possible embodiment, the first compound is a polyethylene glycol resin, and the preparation method comprises:

S1: Resin p reacts with thionyl chloride to obtain compound q;

S2: Compound q reacts with magnesium chloride to obtain compound r through substitution addition reaction; compound r reacts with dialkylsilane to obtain compound s through substitution reaction;

S3: Compound s reacts with an aromatic halide through a catalytic coupling reaction to obtain a silicone-based resin compound t;

The reaction process of the preparation method is as follows:

Wherein, P is polyethylene glycol resin, Z is one of Cl, Br, and I, p is resin p, q is compound q, r is compound r, s is compound s, and t is silicon-based resin compound t.

The third technical problem to be solved by the present invention is to provide the application of the above-mentioned silicon-based resin compounds to solve the problems of harsh reaction conditions, low radiochemical yield, many side reactions and easy damage to the labeled substance in conventional radioactive labeling.

In order to solve the above problems, the present invention provides an application of the silicon-based resin compound, which includes applying the silicon-based resin compound to radioactive labeling.

In a possible embodiment, the application includes applying the silicon-based resin compound to radioactive labeling, including: subjecting the silicon-based resin compound to an electrophilic substitution reaction with ¹³¹ I/ ¹²⁴ I/ ¹²⁷ I/ ²¹¹ At- to obtain an aryl iodine compound or an aryl astatine compound, and then separating the labeled product by filtration to complete the radioactive labeling.

In a possible embodiment, the reaction conditions are: temperature 20-50° C., pH 5.0-7.0.

The application of the silicon-based resin compound in the present invention avoids the shortcomings of the traditional labeling method and provides an application of the silicon-based resin compound, which is particularly suitable for iodine isotope and astatine isotope labeling in medical imaging, targeted radiotherapy and biological research; the silicon-based resin in the present invention has the following components: an organic silicon polymer as a matrix, a functionalized phenylsilane as an active site, and the functionalized group of the present invention includes but is not limited to alkylaryl silane. Through the silicon-based resin of the present invention, efficient radioactive iodine (such as iodine-124, iodine-131) and astatine-211 labeling reactions can be achieved under mild conditions.

By using the silicon-based resin compounds in the present invention, the radiochemical yield of radioactive iodine/astatine labeling can be significantly improved, the occurrence of side reactions can be reduced, and the subsequent separation and purification steps can be simplified to directly obtain high-purity labeled products. The applied technology can be widely used in the fields of nuclear medicine imaging, radioactive tracing, tumor targeted therapy, etc., significantly improving the performance and clinical application value of related products.

BRIEF DESCRIPTION OF THE DRAWINGS

FIG1 is a Radio-TLC thin layer scanner scanning curve diagram of Example 1;

FIG2 is a Radio-TLC thin layer scanner scanning result of Example 1;

FIG3 is a Radio-TLC thin layer scanner scanning curve diagram of Example 2;

FIG. 4 is the scanning result of Radio-TLC thin layer scanner of Example 2.

DETAILED DESCRIPTION

First, those skilled in the art should understand that these implementations are only used to explain the technical principles of the embodiments of the present application, and are not intended to limit the protection scope of the embodiments of the present application. Those skilled in the art can make adjustments to them as needed to adapt to specific application scenarios.

The present application is further described in detail below with reference to the accompanying drawings and specific embodiments.

The present invention provides a silicon-based resin compound, wherein the silicon-based resin compound has a structure as shown in formula (I):

Wherein, P is a resin, and the resin is one of Wang resin, chloromethyl polystyrene resin, and polyethylene glycol resin; X is one of -CH ₂ CH ₂ CH ₂ -, -O(CH ₂ CH ₂ OCH ₂ CH ₂ ) _n CH ₂ CH ₂ -, and -O(CH ₂ CH ₂ OCH ₂ CH ₂ ) _n CH ₂ CH ₂ O-; Y is one of -Me, -Et, -CH(CH ₃ ) ₂ , and -C(CH ₃ ) ₃ ; and Ar is an aromatic hydrocarbon group.

The silicone-based resin compound of the present invention has the following advantages:

As a preferred embodiment, the aromatic hydrocarbon group is

One of them.

As a preferred solution, the polymerization degree of the silicone-based resin compound is less than 4000.

The second technical problem to be solved by the present invention is to provide a method for preparing a silicone-based resin compound to solve the problem that the conventional preparation method has complicated steps and high costs.

In order to solve the above technical problems, the present invention provides a method for preparing the silicone-based resin compound, the preparation method comprising:

S1: taking a first compound containing a P resin and subjecting it to a substitution reaction to obtain a second compound;

S2: subjecting the second compound to at least one addition and/or substitution addition reaction to obtain a third compound;

S3: subjecting the third compound to a catalytic coupling reaction with an aromatic halide to obtain a silicon-based resin compound.

In a possible embodiment, the first compound is chloromethyl polystyrene resin, and the preparation method comprises:

S1: Resin a and magnesium chloride are reacted by substitution to obtain compound b;

S2: Compound b reacts with silane to obtain compound c;

S3: Compound c and an aromatic halide are subjected to a catalytic coupling reaction to obtain a silicon-based resin compound d, which is the silicon-based resin compound;

The reaction process of the preparation method is as follows:

In the formula, Z is one of Cl, Br, and I, a is resin a, b is compound b, c is compound c, and d is silicon-based resin compound d.

As a preferred solution, the first compound is Wang resin, and the preparation method comprises:

S1: Resin e and triphenylphosphine bromide undergo substitution reaction to obtain compound f;

S2: Compound f is reacted with magnesium chloride to obtain compound g through substitution addition reaction, and compound g is reacted with dialkylsilane to obtain compound h through addition reaction;

S3: Compound h and aryl halide undergo catalytic coupling reaction to obtain silicone-based resin compound i;

The reaction process of the preparation method is as follows:

In the formula, Z is one of Cl, Br, and I, e is resin e, f is reactant f, g is compound g, h is compound h, and i is silicon-based resin compound i.

As a preferred solution, the first compound is Wang resin or chloromethyl polystyrene resin, and the preparation method comprises:

S1: Resin j and polyethylene glycol undergo substitution reaction to obtain compound k;

S2: Compound k is reacted with thionyl chloride to obtain compound l through substitution and addition reaction; compound l is reacted with magnesium chloride to obtain compound m through substitution reaction; compound m is reacted with dialkylsilane to obtain compound n through addition reaction;

S3: Compound n is reacted with an aromatic halide by catalytic coupling reaction to obtain a silicon-based resin compound o; wherein n<4000, is a resin selected from: Wang resin, chloromethyl polystyrene resin, Z is selected from: Cl, Br, I, Y refers to the same as described in claim 1, and Ar refers to the same as described in claim 1;

The reaction process of the preparation method is as follows:

In the formula, Z is one of Cl, Br, and I, j is resin j, k is compound k, l is compound l, m is compound m, n is compound n, and o is silicone-based resin compound o.

As a preferred solution, the first compound is a polyethylene glycol resin, and the preparation method comprises:

S1: Resin p reacts with thionyl chloride to obtain compound q;

S2: Compound q reacts with magnesium chloride to obtain compound r through substitution addition reaction; compound r reacts with dialkylsilane to obtain compound s through substitution reaction;

S3: Compound s reacts with an aromatic halide through a catalytic coupling reaction to obtain a silicone-based resin compound t;

The reaction process of the preparation method is as follows:

Wherein, P is polyethylene glycol resin, Z is one of Cl, Br, and I, p is resin p, q is compound q, r is compound r, s is compound s, and t is silicon-based resin compound t.

The third technical problem to be solved by the present invention is to provide the application of the above-mentioned silicon-based resin compounds to solve the problems of harsh reaction conditions, low radiochemical yield, many side reactions and easy damage to the labeled substance in conventional radioactive labeling.

In order to solve the above problems, the present invention provides an application of the silicon-based resin compound, and the application includes applying the silicon-based resin compound to radioactive labeling, including: subjecting the silicon-based resin compound to an electrophilic substitution reaction with ¹³¹ I/ ¹²⁴ I/ ¹²⁷ I/ ²¹¹ At- to obtain an aryl iodine compound or an aryl astatine compound, and then separating the labeled product by filtration to complete the radioactive labeling.

As a preferred solution, the reaction conditions are: temperature 20-50°C, pH 5.0-7.0.

In the following, in combination with specific experimental data and operating methods, embodiments are provided to further expand the above technical solutions of the present invention:

Example 1

This embodiment provides a silicon-based resin compound 3 and a preparation method thereof, and the reaction formula of the preparation process is as follows:

The preparation method comprises:

S1: Synthesis steps of compound 1:

2.0 g of chloromethyl polystyrene resin was placed in a reaction bottle, 20 mL of anhydrous toluene was added under nitrogen protection, and the mixture was stirred at room temperature for 10 minutes. Subsequently, 10 mL of allyl magnesium chloride (2.0 M in the THF) was added dropwise into the reaction bottle and reacted for 30 minutes. The mixture was then heated to 60°C and reacted for 12 hours. After the reaction was completed, the mixture was filtered and the filter residue was washed three times with tetrahydrofuran. Subsequently, the filter residue was placed in a reaction bottle, 22.5 mL of tetrahydrofuran was added, and 7.5 mL of 1N hydrochloric acid solution was added during stirring. After the addition was completed, the reaction temperature was raised to 45°C and the mixture was reacted for 12 hours. After the reaction was completed, the mixture was filtered and the filter residue was washed three times with methanol and dichloromethane, respectively, and then dried in vacuo.

Infrared data of Compound 1: 1640 cm ^-1 (C＝C).

S2: Synthesis steps of compound 2:

2.0 g of compound 1 was placed in a reaction bottle, followed by the addition of 18.5 mg of RhCl(PPh ₃ ) ₃ , and under nitrogen protection, 20 mL of anhydrous toluene was added to react at room temperature for 5 minutes, followed by the addition of 1.6 mL of diethylsilane, and the reaction was carried out at room temperature for 12 hours. After the reaction was completed, the filter was filtered, and the residue was washed three times with ethyl acetate and dichloromethane, respectively, and then dried in vacuo.

Infrared data of compound 2: 2110 cm ^-1 (Si-H), 1230 cm ^-1 (Si-C).

S3: Synthesis steps of compound 3:

500 mg of compound 2 was placed in a reaction bottle, and 286 mg of tert-butyl (3-bromobenzyl)carbamate, 295 mg of potassium acetate, 91 mg of tri(o-methylphenyl)phosphine, and 52 mg of tri(dibenzylideneacetone)dipalladium(0)-chloroform adduct were added. 10 mL of N-methylpyrrolidone was added under nitrogen protection, and the mixture was reacted at 125°C for 20 hours. After the reaction was completed, the mixture was filtered and the residue was washed three times with N,N-dimethylformamide, 1N hydrochloric acid solution, methanol, and dichloromethane, respectively, and then dried in vacuo.

Infrared data of compound 3: 3450 cm ^-1 (NH ).

Example 2

This embodiment provides a silicon-based resin compound 3 and a preparation method thereof, and the reaction formula of the preparation process thereof is as follows:

The preparation method comprises:

S1: Synthesis steps of compound 4:

4.0 g of chloromethyl polystyrene resin was placed in a reaction bottle, 40 mL of 1,4-dioxane was added, and then a mixed solution of 35 g of polyethylene glycol (polyethylene glycol-400) and 100 mL of 33% sodium hydroxide aqueous solution was added dropwise at room temperature. After the addition was completed, the temperature was raised to 50°C and reacted for 10 hours. After the reaction was completed, the filter was filtered and the residue was washed three times with water, 1N hydrochloric acid solution, water, methanol and dichloromethane, respectively, and then vacuum dried.

Infrared data of compound 4: 3200 cm ^-1 (OH).

S2: Synthesis steps of compound 5:

1.5 g of compound 4 was placed in a reaction bottle, and 10 mL of dichlorothionyl was added, followed by reaction at 100° C. for 12 hours. After the reaction was completed, the filter was filtered and the residue was washed three times with dichloromethane, methanol and dichloromethane respectively, and then dried in vacuum.

Infrared data of compound 5: 760 cm ^-1 (C-Cl).

Synthesis steps of compound 6:

1.5 g of chloromethyl polystyrene resin was placed in a reaction bottle, 20 mL of anhydrous toluene was added under nitrogen protection, and the mixture was stirred at room temperature for 10 minutes. Subsequently, 10 mL of allyl magnesium chloride (2.0 M in the THF) was added dropwise into the reaction bottle and reacted for 30 minutes. The mixture was then heated to 60°C and reacted for 12 hours. After the reaction was completed, the mixture was filtered and the residue was washed three times with tetrahydrofuran. Subsequently, the residue was placed in a reaction bottle, 22.5 mL of tetrahydrofuran was added, and 7.5 mL of 1N hydrochloric acid solution was added during stirring. After the addition was completed, the reaction temperature was raised to 45°C and the mixture was reacted for 12 hours. After the reaction was completed, the mixture was filtered and the residue was washed three times with methanol and dichloromethane, respectively, and then dried in vacuo.

Infrared data of compound 6: 1639 cm ^-1 (C＝C).

Synthesis steps of compound 7:

1.5 g of compound 6 was placed in a reaction bottle, followed by the addition of 18.5 mg of RhCl(PPh ₃ ) ₃ , and under nitrogen protection, 20 mL of anhydrous toluene was added to react at room temperature for 5 minutes, followed by the addition of 1.6 mL of diethylsilane, and the reaction was continued at room temperature for 12 hours. After the reaction was completed, the filter was filtered, and the residue was washed three times with ethyl acetate and dichloromethane, respectively, and then dried in vacuo.

Infrared data of compound 6: 2107 cm ^-1 (Si-H), 1232 cm ^-1 (Si-C).

S3: Synthesis steps of compound 7:

500 mg of compound 7 was placed in a reaction bottle, and 286 mg of tert-butyl (3-bromobenzyl)carbamate, 295 mg of potassium acetate, 91 mg of tri(o-methylphenyl)phosphine, and 52 mg of tri(dibenzylideneacetone)dipalladium(0)-chloroform adduct were added. 10 mL of N-methylpyrrolidone was added under nitrogen protection, and the mixture was reacted at 125°C for 20 hours. After the reaction was completed, the mixture was filtered and the residue was washed three times with N,N-dimethylformamide, 1N hydrochloric acid solution, methanol, and dichloromethane, respectively, and then dried in vacuo.

Infrared data of compound 7: 3440 cm ^-1 (NH ).

The following provides an application of the silicon-based resin compound prepared in Example 1 of the present invention, wherein the application includes applying the silicon-based resin compound to labeling [ ¹³¹ I]NaI.

Radiolabeling experiment 1:

The reaction process includes:

Specifically, [ ^131I ]NaI (200μCi, 200μLMeOH) was added to a vial containing 10 mg of labeled resin precursor. Then, 20μL of N-chlorosuccinimide glacial acetic acid solution (0.3M) was added to the vial and stirred at room temperature for 30 minutes. After the reaction was completed, 40μL of saturated sodium sulfite solution was added. Aluminum silica gel plates (developing agent, petroleum ether: ethyl acetate = 10:1) were used for development and scanned with a Radio-TLC thin layer scanner, and the RCC was measured to be 6%.

Radiolabeling experiment 2:

The reaction process includes:

Specifically, [ ^131I ]NaI (200μCi, 200μLMeOH) was added to a vial containing 10 mg of labeled resin precursor. Then, 20μL of N-chlorosuccinimide glacial acetic acid solution (0.3M) was added to the vial and stirred at room temperature for 30 minutes. After the reaction, 40μL of saturated sodium sulfite solution was added. Aluminum silica gel plates (developing agent, petroleum ether: ethyl acetate = 10:1) were used for development and scanned with a Radio-TLC thin layer scanner, and the RCC was measured to be 16%.

As shown in Figures 1 to 4, Figure 1 is a scanning curve diagram of the Radio-TLC thin layer scanner of Example 1; Figure 2 is a scanning result of the Radio-TLC thin layer scanner of Example 1; Figure 3 is a scanning curve diagram of the Radio-TLC thin layer scanner of Example 2;

FIG4 is the scanning result of the Radio-TLC thin layer scanner of Example 2. FIG1-4 further proves that, compared with the previous labeling method, the present invention achieves the advantage of not requiring HPLC separation and can avoid long-term exposure of radionuclides during the separation process.

In the description of the embodiments of the present application, it should be noted that in the description of the present application, terms such as "inside" and "outside" indicating directions or positional relationships are based on the directions or positional relationships shown in the drawings. This is only for the convenience of description, and does not indicate or imply that the device or component must have a specific orientation, be constructed and operated in a specific orientation. Therefore, it cannot be understood as a limitation on the present application.

In the description of the present application, the description with reference to the terms "one embodiment", "some embodiments", "in the present embodiment", "specific example", or "some examples" etc. means that the specific features, mechanisms, materials or characteristics described in conjunction with the embodiment or example are included in at least one embodiment or example of the present application. In this specification, the schematic representations of the above terms do not necessarily refer to the same embodiment or example. Moreover, the specific features, mechanisms, materials or characteristics described may be combined in a suitable manner in any one or more embodiments or examples. In addition, those skilled in the art may combine and combine the different embodiments or examples described in this specification and the features of the different embodiments or examples, without contradiction.

The above is only a specific implementation of the present application, but the protection scope of the present application is not limited thereto. Any changes or substitutions that can be easily thought of by a person skilled in the art within the technical scope disclosed in the present application should be included in the protection scope of the present application. Therefore, the protection scope of the present application shall be based on the protection scope of the claims.

Claims (10)

1. A silicon-based resin compound, characterized in that the silicon-based resin compound has a structure as shown in formula (I): Wherein, P is a resin, and the resin is one of Wang resin, chloromethyl polystyrene resin, and polyethylene glycol resin; X is one of -CH ₂ CH ₂ CH ₂ -, -O(CH ₂ CH ₂ OCH ₂ CH ₂ ) _n CH ₂ CH ₂ -, and -O(CH ₂ CH ₂ OCH ₂ CH ₂ ) _n CH ₂ CH ₂ O-; Y is one of -Me, -Et, -CH(CH ₃ ) ₂ , and -C(CH ₃ ) ₃ ; and Ar is an aromatic hydrocarbon group. 2. The silicon-based resin compound according to claim 1, characterized in that the aromatic hydrocarbon group is One of them. 3 . The silicon-based resin compound according to claim 1 , wherein the degree of polymerization of the silicon-based resin compound is less than 4000. 4. A method for preparing the silicon-based resin compound according to any one of claims 1 to 3, characterized in that the preparation method comprises: S1: taking a first compound containing a P resin and subjecting it to a substitution reaction to obtain a second compound; S2: subjecting the second compound to at least one addition and/or substitution addition reaction to obtain a third compound; S3: subjecting the third compound to a catalytic coupling reaction with an aromatic halide to obtain a silicon-based resin compound. 5. The method for preparing a silicon-based resin compound according to claim 4, wherein the first compound is a chloromethyl polystyrene resin, and the preparation method comprises: S1: Resin a and magnesium chloride are reacted by substitution to obtain compound b; S2: Compound b reacts with silane to obtain compound c; S3: Compound c and an aromatic halide are subjected to a catalytic coupling reaction to obtain a silicon-based resin compound d, which is the silicon-based resin compound; The reaction process of the preparation method is as follows: In the formula, Z is one of Cl, Br, and I, a is resin a, b is compound b, c is compound c, and d is silicon-based resin compound d. 6. The method for preparing a silicon-based resin compound according to claim 4, wherein the first compound is Wang resin, and the preparation method comprises: S1: Resin e and triphenylphosphine bromide undergo substitution reaction to obtain compound f; S2: Compound f is reacted with magnesium chloride to obtain compound g through substitution addition reaction, and compound g is reacted with dialkylsilane to obtain compound h through addition reaction; S3: Compound h and aryl halide undergo catalytic coupling reaction to obtain silicone-based resin compound i; The reaction process of the preparation method is as follows: In the formula, Z is one of Cl, Br, and I, e is resin e, f is reactant f, g is compound g, h is compound h, and i is silicon-based resin compound i. 7. The method for preparing a silicon-based resin compound according to claim 4, wherein the first compound is Wang resin or chloromethyl polystyrene resin, and the preparation method comprises: S1: Resin j and polyethylene glycol undergo substitution reaction to obtain compound k; S2: Compound k is reacted with thionyl chloride to obtain compound l through substitution and addition reaction; compound l is reacted with magnesium chloride to obtain compound m through substitution reaction; compound m is reacted with dialkylsilane to obtain compound n through addition reaction; S3: Compound n is reacted with an aromatic halide by catalytic coupling reaction to obtain a silicon-based resin compound o; wherein n<4000, is a resin selected from: Wang resin, chloromethyl polystyrene resin, Z is selected from: Cl, Br, I, Y refers to the same as described in claim 1, and Ar refers to the same as described in claim 1; The reaction process of the preparation method is as follows: In the formula, Z is one of Cl, Br, and I, j is resin j, k is compound k, l is compound l, m is compound m, n is compound n, and o is silicone-based resin compound o. 8. The method for preparing a silicon-based resin compound according to claim 4, wherein the first compound is a polyethylene glycol resin, and the preparation method comprises: S1: Resin p reacts with thionyl chloride to obtain compound q; S2: Compound q reacts with magnesium chloride to obtain compound r through substitution addition reaction; compound r reacts with dialkylsilane to obtain compound s through substitution reaction; S3: Compound s reacts with an aromatic halide through a catalytic coupling reaction to obtain a silicone-based resin compound t; The reaction process of the preparation method is as follows: Wherein, P is polyethylene glycol resin, Z is one of Cl, Br, and I, p is resin p, q is compound q, r is compound r, s is compound s, and t is silicon-based resin compound t. 9. An application of the silicon-based resin compound according to any one of claims 1 to 3, characterized in that the application comprises applying the silicon-based resin compound to radioactive labeling, comprising: subjecting the silicon-based resin compound to an electrophilic substitution reaction with ¹³¹ I/ ¹²⁴ I/ ¹²⁷ I/ ²¹¹ At- to obtain an aryl iodine compound or an aryl astatine compound, and then separating the labeled product by filtration to complete the radioactive labeling. 10. The use according to claim 9, characterized in that the reaction conditions are: temperature 20-50°C, pH 5.0-7.0.