A silicone-based resin compound, its preparation method and application

Abstract

The present invention provides a silicon-based resin compound, and the silicon-based resin compound has a structure shown in formula (I). The present invention also provides a preparation method of the silicon-based resin compound, including: S1: obtaining a second compound by subjecting a first compound containing a P resin to a substitution reaction; S2: obtaining a third compound by subjecting the second compound to at least one addition and / or substitution addition reaction; S3: obtaining a silicon-based resin compound by subjecting the third compound to a catalytic coupling reaction with an aryl halide. The present invention also provides an application of the silicon-based resin compound in radioactive labeling. By the silicon-based resin compound and its application of 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, and a high-purity labeled product can be directly obtained.

Description

Technical Field

[0001] The present invention relates to the field of silicon-based resin compounds, and in particular, to a silicon-based resin compound, a preparation method thereof, and an application thereof. Background Art

[0002] Radioactive labeling techniques have important applications in fields such as nuclear medicine imaging, radioactive tracer studies, and tumor targeted therapy. These techniques use radioactive isotopes (such as iodine-123, iodine-124, iodine-125, iodine-131, and astatine-211) to label specific drugs or biomolecules, so as to clearly display the lesion site in medical imaging or directly act on tumor cells in treatment. However, existing radioactive iodine / astatine labeling methods have some limitations. There are problems in the reaction method itself, including harsh reaction conditions, low radiochemical yield, many side reactions, and the need for 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.

[0003] The main products and methods of existing radioactive iodine / astatine labeling techniques include:

[0004] Direct labeling method: The direct labeling method of iodine is a relatively common radioactive iodine labeling method, and the labeling principle is shown in the following formula:

[0005]

[0006] Its labeling process mainly involves electrophilic substitution reactions. *I- undergoes an oxidation reaction under the action of an oxidant to generate *I2 or *I + , and then electrophilic substitution occurs on the hydrogen atoms of specific groups of aromatic compounds in the target molecule or drug (such as tyrosine, phenylalanine, tryptophan, and histidine contained in proteins and polypeptides, and active rings such as benzene rings and phenol rings). The direct labeling method has advantages such as high radiochemical yield, simple operation, and cheap reagents. However, the raw material used in this method is a strong oxidant, which may damage sensitive substances to be labeled (such as receptors and hormones with unstable biological activities). For example, the cleavage of tryptophan peptide bonds, the oxidation of thiol or thioether groups in the structure, resulting in the loss of biological activity of the substance to be labeled, etc.

[0007] Indirect labeling method: The indirect labeling method is relative to the direct labeling method in which the substance to be labeled is directly coupled with a radionuclide. In this method, most of the time, an intermediate or precursor substance is first combined with a drug or biomolecule, and then radioactive iodine labeling is carried out. At least two steps of reactions are required to obtain a labeled substance with the structure of "radionuclide + auxiliary group + target molecule or drug", and the labeling principle is shown in the following formula.

[0008]

[0009] Although this method can alleviate the extreme reaction conditions of the direct labeling method to a certain extent, there are still problems such as harsh reaction conditions, low radiochemical yield, and many side reactions. Although the indirect radioactive iodine labeling method can broaden the range of molecules to be labeled and improve the stability of the labeled products to a certain extent, its labeling process requires multiple reactions, and the radiochemical yield is an important issue to consider. Moreover, the cost of preparing radioactive labeled compounds by conventional methods is high, and the steps are cumbersome. Summary of the Invention

[0010] The first technical problem to be solved by the present invention is to provide a silicone resin compound to solve the problems of harsh reaction conditions, low radiochemical yield, many side reactions, and easy damage to the molecule to be labeled in conventional radioactive labeling.

[0011] To solve the above technical problems, the present invention provides a silicone resin compound, and the silicone resin compound has a structure shown in formula (I):

[0012]

[0013] wherein, P is a resin, and the resin is one of Wang resin, chloromethyl polystyrene resin, and polyethylene glycol resin; X is -CH2CH2CH2-, -O(CH2CH2OCH2CH2) n CH2CH2-, -O(CH2CH2OCH2CH2) n CH2CH2O-; Y is one of -Me, -Et, -CH(CH3)2, -C(CH3)3; Ar is an aromatic hydrocarbon group.

[0014] Compared with the prior art, the silicone resin compound in the present invention has the following advantages:

[0015] 1) The silicone resin compound in the present invention has high radioactive iodine / astatine binding ability, ensuring the completeness and stability of the labeling reaction;

[0016] 2) The silicone resin compound in the present invention has excellent chemical stability and biocompatibility, and is suitable for the labeling of various drug molecules;

[0017] 3) The silicone resin compound in the present invention has the advantages of simple operation and mild conditions in actual application, and is suitable for laboratory and industrial production.

[0018] In a possible implementation manner, the aromatic hydrocarbon group is

[0019] one of them.

[0020] In one possible implementation, the degree of polymerization of the silicone resin compound is less than 4000.

[0021] The second technical problem to be solved by the present invention is to provide a method for preparing a silicone resin compound to solve the problems of cumbersome steps and high cost in conventional preparation methods.

[0022] To solve the above technical problems, the present invention provides a method for preparing the silicone resin compound, and the preparation method includes:

[0023] S1: Taking a first compound containing a P resin to obtain a second compound through a substitution reaction;

[0024] S2: Subjecting the second compound to at least one addition and / or substitution addition reaction to obtain a third compound;

[0025] S3: Subjecting the third compound and an aryl halide to a catalytic coupling reaction to obtain a silicone resin compound.

[0026] Through the above preparation method of the present invention, a method for preparing a silicone resin compound without cumbersome steps and with simple operation is provided, overcoming the problems of high cost and cumbersome steps of the labeled compounds used in radioactivity in the prior art.

[0027] In one possible implementation, the first compound is chloromethyl polystyrene resin, and the preparation method includes:

[0028] S1: Resin a reacts with allylmagnesium chloride through a substitution reaction to obtain compound b;

[0029] S2: Compound b reacts with silane through an addition reaction to obtain compound c;

[0030] S3: Compound c reacts with an aryl halide through a catalytic coupling reaction to obtain a silicone resin compound d, which is the silicone resin compound;

[0031] The reaction process of the preparation method is as follows:

[0032]

[0033] 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 silicone resin compound d.

[0034] In one possible implementation, the first compound is Wang resin, and the preparation method includes:

[0035] S1: Resin e reacts with triphenylphosphine bromide through a substitution reaction to obtain compound f;

[0036] S2: Compound f reacts with magnesium allyl chloride through a substitution addition reaction to obtain compound g, and compound g reacts with a dialkylsilane through an addition reaction to obtain compound h;

[0037] S3: Compound h reacts with an aryl halide through a catalytic coupling reaction to obtain a silyl resin compound i;

[0038] The reaction process of the preparation method is as follows:

[0039]

[0040] 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 silyl resin compound i.

[0041] In a possible implementation manner, the first compound is Wang resin or chloromethyl polystyrene resin, and the preparation method includes:

[0042] S1: Resin j reacts with polyethylene glycol through a substitution reaction to obtain compound k;

[0043] S2: Compound k reacts with thionyl dichloride through a substitution addition reaction to obtain compound l; compound l reacts with magnesium allyl chloride through a substitution reaction to obtain compound m; compound m reacts with a dialkylsilane through an addition reaction to obtain compound n;

[0044] S3: Compound n reacts with an aryl halide through a catalytic coupling reaction to obtain a silyl resin compound o; where 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;

[0045] The reaction process of the preparation method is as follows:

[0046]

[0047] 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 silyl resin compound o.

[0048] In a possible implementation manner, the first compound is a polyethylene glycol resin, and the preparation method includes:

[0049] S1: Resin p reacts with thionyl dichloride through a substitution reaction to obtain compound q;

[0050] S2: Compound q reacts with magnesium allyl chloride through a substitution addition reaction to obtain compound r; compound r reacts with a dialkylsilane through a substitution reaction to obtain compound s;

[0051] S3: The compound s and the aryl halide are subjected to a catalytic coupling reaction to obtain a silyl resin compound t;

[0052] The reaction process of the preparation method is as follows:

[0053]

[0054] Wherein, P is a polyethylene glycol resin, Z is one of Cl, Br, and I, p is a resin p, q is a compound q, r is a compound r, s is a compound s, and t is a silyl resin compound t.

[0055] The third technical problem to be solved by the present invention is to provide an application of the above-mentioned silyl resin compound to solve the problems of harsh reaction conditions, low radiochemical yield, many side reactions, and easy damage to the substance to be labeled in conventional radiolabeling.

[0056] To solve the above problems, the present invention provides an application of the silyl resin compound, and the application includes applying the silyl resin compound to radiolabeling.

[0057] In a possible implementation manner, the application including applying the silyl resin compound to radiolabeling includes: reacting the silyl resin compound with 131 I / 124 I / 127 I / 211 At- to carry out an electrophilic substitution reaction to obtain an aryl iodide compound or an aryl astatide compound. Subsequently, the labeled product is separated by filtration to complete the radiolabeling.

[0058] In a possible implementation manner, the conditions of the reaction are: temperature 20 - 50 °C, pH 5.0 - 7.0.

[0059] The application of the silyl resin compound in the present invention avoids the disadvantages of traditional labeling methods and provides an application of the silyl resin compound, which is particularly suitable for the labeling of iodine isotopes and astatine isotopes in medical imaging, targeted radiotherapy, and biological research; the silyl resin-containing resin in the present invention has the following components: an organosilicon polymer as a matrix and a functionalized phenylsilane as an active site. The functional groups of the present invention include, but are not limited to, alkylaryl silanes. Through the silyl resin-containing resin of the present invention, efficient radiolabeling reactions of radioactive iodine (such as iodine-124, iodine-131) and astatine-211 can be achieved under mild conditions.

[0060] Through the application of the silicone resin-based compound in the present invention, the radiochemical yield of radioiodine / 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 a labeled product with high purity. The technology of this application can be widely used in the fields of nuclear medicine imaging, radioactive tracing, tumor targeted therapy, etc., significantly enhancing the performance and clinical application value of related products. BRIEF DESCRIPTION OF THE DRAWINGS

[0061] Figure 1 It is the scanning curve graph of the Radio-TLC thin layer scanner for Example 1;

[0062] Figure 2 It is the scanning result of the Radio-TLC thin layer scanner for Example 1;

[0063] Figure 3 It is the scanning curve graph of the Radio-TLC thin layer scanner for Example 2;

[0064] Figure 4 It is the scanning result of the Radio-TLC thin layer scanner for Example 2. DETAILED DESCRIPTION OF THE EMBODIMENTS

[0065] First of all, those skilled in the art should understand that these embodiments 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 according to needs to adapt to specific application scenarios.

[0066] The present application will be further described in detail below with reference to the accompanying drawings and specific embodiments.

[0067] The present invention provides a silicone resin-based compound, and the silicone resin-based compound has a structure shown in formula (I):

[0068]

[0069] Wherein, P is a resin, and the resin is one of Wang resin, chloromethyl polystyrene resin, and polyethylene glycol resin; X is -CH2CH2CH2-, -O(CH2CH2OCH2CH2) n CH2CH2-, -O(CH2CH2OCH2CH2) n CH2CH2O-; Y is one of -Me, -Et, -CH(CH3)2, -C(CH3)3; Ar is an aromatic hydrocarbon group.

[0070] The silicone resin-based compound in the present invention has the following advantages:

[0071] As a preferred scheme, the aromatic hydrocarbon group is

[0072] one of the following.

[0073] As a preferred solution, the degree of polymerization of the silicone resin compound is less than 4000.

[0074] The second technical problem to be solved by the present invention is to provide a preparation method of a silicone resin compound to solve the problems of cumbersome steps and high cost in the conventional preparation method.

[0075] To solve the above technical problems, the present invention provides a preparation method of the silicone resin compound, and the preparation method includes:

[0076] S1: Obtaining a second compound by subjecting a first compound containing a P resin to a substitution reaction;

[0077] S2: Obtaining a third compound by subjecting the second compound to at least one addition and / or substitution addition reaction;

[0078] S3: Obtaining a silicone resin compound by subjecting the third compound to a catalytic coupling reaction with an aryl halide.

[0079] In a possible implementation manner, the first compound is a chloromethyl polystyrene resin, and the preparation method includes:

[0080] S1: Reacting resin a with magnesium allyl chloride by a substitution reaction to obtain compound b;

[0081] S2: Reacting compound b with silane by an addition reaction to obtain compound c;

[0082] S3: Reacting compound c with an aryl halide by a catalytic coupling reaction to obtain a silicone resin compound d, which is the silicone resin compound;

[0083] The reaction process of the preparation method is as follows:

[0084]

[0085] 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 silicone resin compound d.

[0086] As a preferred solution, the first compound is Wang resin, and the preparation method includes:

[0087] S1: Reacting resin e with triphenylphosphine bromide by a substitution reaction to obtain compound f;

[0088] S2: Compound f reacts with magnesium allyl chloride through a substitution addition reaction to obtain compound g, and compound g reacts with a dialkylsilane through an addition reaction to obtain compound h;

[0089] S3: Compound h reacts with an aryl halide through a catalytic coupling reaction to obtain a silyl resin compound i;

[0090] The reaction process of the preparation method is as follows:

[0091]

[0092] 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 silyl resin compound i.

[0093] As a preferred embodiment, the first compound is Wang resin or chloromethyl polystyrene resin, and the preparation method includes:

[0094] S1: Resin j reacts with polyethylene glycol through a substitution reaction to obtain compound k;

[0095] S2: Compound k reacts with thionyl dichloride through a substitution addition reaction to obtain compound l; compound l reacts with magnesium allyl chloride through a substitution reaction to obtain compound m; compound m reacts with a dialkylsilane through an addition reaction to obtain compound n;

[0096] S3: Compound n reacts with an aryl halide through a catalytic coupling reaction to obtain a silyl resin compound o; where n < 4000, it is a resin, selected from: Wang resin, chloromethyl polystyrene resin, Z is selected from: Cl, Br, I, Y is the same as defined in claim 1, and Ar is the same as defined in claim 1;

[0097] The reaction process of the preparation method is as follows:

[0098]

[0099] 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 silyl resin compound o.

[0100] As a preferred embodiment, the first compound is polyethylene glycol resin, and the preparation method includes:

[0101] S1: Resin p reacts with thionyl dichloride through a substitution reaction to obtain compound q;

[0102] S2: Compound q reacts with magnesium allyl chloride through a substitution addition reaction to obtain compound r; compound r reacts with a dialkylsilane through a substitution reaction to obtain compound s;

[0103] S3: Compound s reacts with an aryl halide through a catalytic coupling reaction to obtain a silyl resin compound t;

[0104] The reaction process of the preparation method is as follows:

[0105]

[0106] Among them, P is a 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 a silicon-based resin compound t.

[0107] The third technical problem to be solved by the present invention is to provide the application of the above-mentioned silicon-based resin compound to solve the problems of harsh reaction conditions, low radiochemical yield, many side reactions, and easy damage to the substance to be labeled in conventional radioisotope labeling.

[0108] 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 radioisotope labeling, including: reacting the silicon-based resin compound with 131 I / 124 I / 127 I / 211 At- to undergo an electrophilic substitution reaction to obtain an aryl iodide compound or an aryl astatide compound. Subsequently, the labeled product is separated by filtration to complete radioisotope labeling.

[0109] As a preferred solution, the conditions of the reaction are: temperature 20 - 50 °C, pH 5.0 - 7.0.

[0110] Hereinafter, in combination with specific experimental data and operation means, examples are provided to further expand the above technical solutions of the present invention:

[0111] Example 1

[0112] This example provides a silicon-based resin compound 3 and its preparation method, and the reaction formula of the preparation reaction process is as follows:

[0113]

[0114] The preparation method includes:

[0115] S1: The synthesis step of compound 1:

[0116] Place 2.0 g of chloromethyl polystyrene resin in a reaction flask. After adding 20 mL of anhydrous toluene under nitrogen protection, stir at room temperature for 10 minutes. Then, slowly add 10 mL of allylmagnesium chloride (2.0 M in THF) dropwise to the reaction flask and react for 30 minutes. Subsequently, raise the temperature to 60 °C and react for 12 hours. After the reaction is completed, perform suction filtration. Wash the filter residue three times with tetrahydrofuran. Then, place the filter residue in the reaction flask, add 22.5 mL of tetrahydrofuran, and add 7.5 mL of 1 N hydrochloric acid solution with stirring. After adding, raise the reaction temperature to 45 °C and react for 12 hours. After the reaction is completed, perform suction filtration. Wash the filter residue three times with methanol and dichloromethane respectively, and then dry it under vacuum.

[0117] IR data of Compound 1: 1640 cm -1 (C=C).

[0118] S2: Synthesis steps of Compound 2:

[0119] Place 2.0 g of Compound 1 in a reaction flask. Then, add 18.5 mg of RhCl(PPh3)3, and add 20 mL of anhydrous toluene under nitrogen protection and react at room temperature for 5 minutes. Subsequently, add 1.6 mL of diethylsilane and react at room temperature for 12 hours. After the reaction is completed, perform suction filtration. Wash the filter residue three times with ethyl acetate and dichloromethane respectively, and then dry it under vacuum.

[0120] IR data of Compound 2: 2110 cm -1 (Si-H), 1230 cm -1 (Si-C).

[0121] S3: Synthesis steps of Compound 3:

[0122] Place 500 mg of Compound 2 in a reaction flask, add 286 mg of tert-butyl (3-bromobenzyl)carbamate, 295 mg of potassium acetate, 91 mg of tris(o-tolyl)phosphine, 52 mg of tris(dibenzylideneacetone)dipalladium(0)-chloroform adduct, and add 10 mL of N-methylpyrrolidone under nitrogen protection and react at 125 °C for 20 hours. After the reaction is completed, perform suction filtration. Wash the filter residue three times with N,N-dimethylformamide, 1 N hydrochloric acid solution, methanol, and dichloromethane respectively, and then dry it under vacuum.

[0123] IR data of Compound 3: 3450 cm -1 (N-H).

[0124] Example 2

[0125] This example provides a silicon-based resin compound 3 and its preparation method. The reaction formula of the preparation reaction process is as follows:

[0126]

[0127] The preparation method includes:

[0128] S1: Synthesis steps of compound 4:

[0129] Place 4.0 g of chloromethyl polystyrene resin in a reaction flask, add 40 mL of 1,4-dioxane, and then dropwise add a mixed solution of 35 g of polyethylene glycol (polyethylene glycol-400) and 100 mL of an aqueous solution of 33% sodium hydroxide at room temperature. After the addition is complete, raise the temperature to 50 °C and react for 10 hours. After the reaction is completed, filter by suction. The filter residue is washed three times with water, 1N hydrochloric acid solution, water, methanol, and dichloromethane, and then dried under vacuum.

[0130] Infrared data of compound 4: 3200 cm -1 (O-H).

[0131] S2: Synthesis steps of compound 5:

[0132] Place 1.5 g of compound 4 in a reaction flask, add 10 mL of thionyl chloride, and then react at 100 °C for 12 hours. After the reaction is completed, filter by suction. The filter residue is washed three times with dichloromethane, methanol, and dichloromethane, and then dried under vacuum.

[0133] Infrared data of compound 5: 760 cm -1 (C-Cl).

[0134] Synthesis steps of compound 6:

[0135] Place 1.5 g of chloromethyl polystyrene resin in a reaction flask. After adding 20 mL of anhydrous toluene under nitrogen protection, stir at room temperature for 10 minutes. Then, gradually add 10 mL of allylmagnesium chloride (2.0 M in THF) dropwise to the reaction flask. After reacting for 30 minutes, raise the temperature to 60 °C and react for 12 hours. After the reaction is completed, filter by suction. The filter residue is washed three times with tetrahydrofuran. Then, place the filter residue in a reaction flask, add 22.5 mL of tetrahydrofuran, and add 7.5 mL of 1N hydrochloric acid solution with stirring. After the addition is complete, raise the reaction temperature to 45 °C and react for 12 hours. After the reaction is completed, filter by suction. The filter residue is washed three times with methanol and dichloromethane, and then dried under vacuum.

[0136] Infrared data of compound 6: 1639 cm -1 (C=C).

[0137] Synthesis steps of compound 7:

[0138] Place 1.5 g of Compound 6 in a reaction flask, then add 18.5 mg of RhCl(PPh3)3, and under nitrogen protection, add 20 mL of anhydrous toluene and react at room temperature for 5 minutes. Then add 1.6 mL of diethylsilane and react at room temperature for 12 hours. After the reaction is completed, filter by suction. Wash the filter residue three times with ethyl acetate and dichloromethane respectively, and then dry under vacuum.

[0139] Infrared data of Compound 6: 2107 cm -1 (Si-H), 1232 cm -1 (Si-C).

[0140] S3: Synthesis steps of Compound 7:

[0141] Place 500 mg of Compound 7 in a reaction flask, add 286 mg of tert-butyl (3-bromobenzyl)carbamate, 295 mg of potassium acetate, 91 mg of tris(o-tolyl)phosphine, 52 mg of tris(dibenzylideneacetone)dipalladium(0)-chloroform adduct, and under nitrogen protection, add 10 mL of N-methylpyrrolidone and react at 125 °C for 20 hours. After the reaction is completed, filter by suction. Wash the filter residue three times with N,N-dimethylformamide, 1N hydrochloric acid solution, methanol, and dichloromethane respectively, and then dry under vacuum.

[0142] Infrared data of Compound 7: 3440 cm -1 (N-H).

[0143] The following provides the applications of the silicon-based resin compounds prepared in Example 1 of the present invention above. The applications include applying the silicon-based resin compounds to 131 I] Labeling of NaI.

[0144] Radioactive labeling experiment 1:

[0145] The reaction process includes:

[0146]

[0147] Specifically: Place 131 I] NaI (200 μCi, 200 μL MeOH) into a vial containing 10 mg of the labeled resin precursor. Then add 20 μL of an ice acetic acid solution of N-chlorosuccinimide (0.3 M) to the vial and stir at room temperature for 30 minutes. After the reaction is completed, add 40 μL of saturated sodium sulfite solution. Develop using an aluminum silica gel plate (developer, petroleum ether: ethyl acetate = 10:1), and scan with a Radio-TLC thin layer scanner. The measured RCC is 6%.

[0148] Radioactive labeling experiment 2:

[0149] The reaction process includes:

[0150]

[0151] Specifically: Add 131 I] NaI (200 μCi, 200 μL MeOH) into a vial containing 10 mg of the labeled resin precursor. Then add 20 μL of an acetic acid solution (0.3 M) of N-chlorosuccinimide to the vial, stir at room temperature for 30 minutes, and add 40 μL of saturated sodium sulfite solution after the reaction ends. Develop using an aluminum silica gel plate (developer, petroleum ether: ethyl acetate = 10:1), and scan with a Radio-TLC thin layer scanner. The RCC is measured to be 16%.

[0152] As Figures 1 - 4 shown, Figure 1 is the scanning curve of the Radio-TLC thin layer scanner for Example 1; Figure 2 is the scanning result of the Radio-TLC thin layer scanner for Example 1; Figure 3 is the scanning curve of the Radio-TLC thin layer scanner for Example 2;

[0153] Figure 4 is the scanning result of the Radio-TLC thin layer scanner for Example 2, Figures 1 - 4 which also further proves that compared with the previous labeling method, the present invention realizes the advantage of not requiring HPLC separation and can avoid the long-term exposure of radionuclides during the separation process.

[0154] 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", "outside", etc., indicating directions or positional relationships are based on the directions or positional relationships shown in the drawings. This is only for 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, and therefore should not be construed as a limitation of the present application.

[0155] In the description of the present application, the description with reference to terms such as "one embodiment", "some embodiments", "in this embodiment", "specific example", or "some examples", etc., means that the specific features, mechanisms, materials, or characteristics described in connection with the embodiment or example are included in at least one embodiment or example of the present application. In this specification, the schematic descriptions of the above terms do not necessarily refer to the same embodiment or example. Moreover, the specific features, mechanisms, materials, or characteristics described can be combined in a suitable manner in any one or more embodiments or examples. In addition, without contradiction, those skilled in the art can combine and combine the different embodiments or examples described in this specification and the features of different embodiments or examples.

[0156] As described above, it is only the specific implementation manner 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 those skilled in the art within the technical scope disclosed in the present application should be covered within the protection scope of the present application. Therefore, the protection scope of the present application shall be subject to the protection scope of the claims.

Claims

1. A preparation method of a silicone resin-based compound, characterized in that, The preparation method includes: S1: Resin a reacts with magnesium allyl chloride through a substitution reaction to obtain compound b; S2: Compound b reacts with silane through an addition reaction to obtain compound c; S3: Compound c reacts with aryl halide through a catalytic coupling reaction to obtain a silyl resin compound d, which is the silyl resin compound; The reaction process of the preparation method is as follows: ； Among them, Y is one of -Me, -Et, -CH(CH3)2, -C(CH3)3, and Ar is an aromatic hydrocarbon group; In ArZ, Z is one of Cl, Br, I, a is resin a, the resin a is chloromethylated polystyrene resin, b is compound b, c is compound c, and d is silyl resin compound d.

2. A preparation method of a silicon-based resin compound, characterized in that, The preparation method includes: S1: Resin e reacts with triphenylphosphine bromide through a substitution reaction to obtain compound f; S2: Compound f reacts with magnesium allyl chloride through a substitution addition reaction to obtain compound g, and compound g reacts with dialkylsilane through an addition reaction to obtain compound h; S3: Compound h reacts with aryl halide through a catalytic coupling reaction to obtain silyl resin compound i; The reaction process of the preparation method is as follows: ； Among them, Y is one of -Me, -Et, -CH(CH3)2, -C(CH3)3, and Ar is an aromatic hydrocarbon group; Z is one of Cl, Br, I, e is resin e, the resin e is Wang resin, f is reactant f, g is compound g, h is compound h, and i is silyl resin compound i.

3. A method for preparing a silicone-based resin compound, characterized in that, The preparation method includes: S1: Resin j reacts with polyethylene glycol through a substitution reaction to obtain compound k; S2: Compound k reacts with thionyl chloride through a substitution addition reaction to obtain compound l; compound l reacts with magnesium allyl chloride through a substitution reaction to obtain compound m; compound m reacts with dialkylsilane through an addition reaction to obtain compound n; S3: Compound n reacts with aryl halide through a catalytic coupling reaction to obtain silyl resin compound o; The reaction process of the preparation method is as follows: ； Among them, Y is one of -Me, -Et, -CH(CH3)2, -C(CH3)3, and Ar is an aromatic hydrocarbon group; In ArZ, Z is one of Cl, Br, I, j is resin j, the resin j is chloromethylated polystyrene resin, k is compound k, l is compound l, m is compound m, n is compound n, and o is silyl resin compound o.

4. A method for preparing a silicone-based resin compound, characterized in that, The preparation method includes: S1: Resin p reacts with thionyl chloride through a substitution reaction to obtain compound q; S2: Compound q reacts with magnesium allyl chloride through a substitution addition reaction to obtain compound r; compound r reacts with dialkylsilane through a substitution reaction to obtain compound s; S3: Compound s reacts with aryl halide through a catalytic coupling reaction to obtain silyl resin compound t; The reaction process of the preparation method is as follows: ； Among them, Y is one of -Me, -Et, -CH(CH3)2, -C(CH3)3, and Ar is an aromatic hydrocarbon group; Z is one of Cl, Br, I, p is resin p, the resin p is polyethylene glycol resin, q is compound q, r is compound r, s is compound s, and t is silyl resin compound t.

5. The preparation method of the silicone resin-based compound according to any one of claims 1-4, characterized in that, The aromatic hydrocarbon group is one of the following.

6. The preparation method of the silicone resin-based compound according to any one of claims 1-4, characterized in that, The degree of polymerization of the silyl resin compound is less than 4000.

7. Use of a silicone resin compound prepared by the preparation method of the silicone resin compound according to any one of claims 1-6, characterized in that, The application includes applying the silicone resin compound to radioactive labeling, including: reacting the silicone resin compound with 131 I, 124 I, 127 I, 211 At through electrophilic substitution reaction to obtain an aryl iodide compound or an aryl astatide compound. Subsequently, the labeled product is separated by filtration to complete the radioactive labeling.

8. The application according to claim 7, wherein The conditions for the reaction are as follows: temperature 20 - 50 °C, pH 5.0 - 7.0.

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