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Novel cholic acid chelating agent modified by guanidinylation of biosterol as well as preparation method and application of cholic acid chelating agent

A technology of biosterol and guanidinylation, which is applied in the field of preparation of bile acid chelating agent, can solve problems such as the influence of thyroid function and gastrointestinal discomfort, and achieve the effect of simple production process, high yield and mild reaction conditions

Active Publication Date: 2022-07-08
ZHEJIANG GONGSHANG UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Most of these bile acid chelating agents are chemically modified polymer amines and ammonium salt resins, which have high bile acid binding ability, but they have side effects such as nausea, vomiting and constipation during use, and even have certain effects on thyroid function. Influence
[0003] Disclose a kind of biocompatible bile acid sequestrant and its preparation method and application as patent No. CN104086789B, this patent discloses specific preparation steps, by first preparing N-hexyl allylamine hydrochloride; Hexyl allyl amine hydrochloride and allyl amine hydrochloride were used as monomers to prepare cationic amphiphilic copolymer precursors; oxidized sugar derivatives were used to prepare biocompatible dialdehyde crosslinkers; crosslinked copolymers A new type of bile acid chelating agent is prepared from the precursor, but this patent is only for the preparation of bile acid chelating agent, and there is no corresponding improvement and modification of the bile acid chelating agent, and there will still be side effects such as gastrointestinal discomfort, diarrhea, and anorexia during use

Method used

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  • Novel cholic acid chelating agent modified by guanidinylation of biosterol as well as preparation method and application of cholic acid chelating agent
  • Novel cholic acid chelating agent modified by guanidinylation of biosterol as well as preparation method and application of cholic acid chelating agent
  • Novel cholic acid chelating agent modified by guanidinylation of biosterol as well as preparation method and application of cholic acid chelating agent

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0049] The preparation method of the bile acid chelating agent modified by stigmasterol guanidation, the steps are as follows:

[0050](1) Under anhydrous and anaerobic conditions, add 0.2 g stigmasterol and 0.18 g triphenylphosphine to 5 mL of ultra-dry tetrahydrofuran solvent, stir well, and cool the mixture to 0 °C, then quickly add 0.15 g diisopropyl azodicarboxylate, and then 0.18 g of diphenylphosphonium azide was added dropwise. After the dropwise addition, the temperature was raised to room temperature, and the reaction was carried out for 22 h, then stirred at 50 °C for 3 h, and then 0.20 g of triphenylphosphonium was added. , heated and stirred at 50 °C for 2 h, and stirred until no gas was formed. Cool to room temperature, add 0.006 g of water, continue to stir for 3 h, cool, spin dry, separate and purify by column chromatography, concentrate, and dry to obtain stigmasterol derivative A as a pale yellow solid with a yield of 55.8%.

[0051] (2) Add 0.050 g of biost...

Embodiment 2

[0053] The preparation method of the bile acid chelating agent modified by stigmasterol guanidation, the steps are as follows:

[0054] (1) Under anhydrous and anaerobic conditions, add 1.00 g of stigmasterol and 0.90 g of triphenylphosphonium to 20 mL of ultra-dry tetrahydrofuran solvent, stir evenly, and cool the mixture to 0 °C, then quickly add 0.75 g diisopropyl azodicarboxylate, followed by dropwise addition of 0.90 g of diphenylphosphoryl azide, after the dropwise addition, the temperature was raised to room temperature, the reaction was carried out for 22 h, and then stirred at 50 °C for 3 h, and then 1.00 g of triphenyl was added. Phosphorus was heated and stirred at 50 °C for 2 h, and stirred until no gas was formed. Cooled to room temperature, added 0.030 g of water, continued to stir for 3 h, cooled, spin-dried, separated and purified by column chromatography, concentrated, and dried to obtain stigmasterol derivative A as a pale yellow solid with a yield of 55.8%. ...

Embodiment 3

[0057] The preparation method of the bile acid chelating agent modified by stigmasterol guanidation, the steps are as follows:

[0058] (1) Under anhydrous and anaerobic conditions, add 5.0 g of stigmasterol and 4.0 g of triphenylphosphonium to 50 mL of ultra-dry tetrahydrofuran solvent, stir evenly, and cool the mixture to 0 °C, then quickly add 3.0 g diisopropyl azodicarboxylate, then 2.8 g diphenylphosphonium azide was added dropwise, after the dropwise addition, it was warmed to room temperature, reacted for 24 h, then stirred at 50 °C for 3 h, and then 4.0 g triphenylphosphonium was added , heated and stirred at 50 °C for 2 h, and stirred until no gas was formed. Cool to room temperature, add 0.1 g of water, continue stirring for 3 h, cool, spin dry, separate and purify by column chromatography, concentrate, and dry to obtain light yellow solid stigmasterol derivative A with a yield of 60.4%.

[0059] (2) 0.850 g of biosterol derivative A prepared in step (1), 0.300 g of...

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Abstract

The invention relates to the technical field of medical small molecule synthesis, in particular to preparation and application of a novel biological sterol guanidinylation modified cholic acid chelating agent, prepared biological sterol derivatives react with pyrazole-1-formamidine hydrochloride and N, N-diisopropylethylamine, and then column chromatography separation and purification and concentration are performed to obtain the novel biological sterol guanidinylation modified cholic acid chelating agent. Compared with a traditional macromolecule resin type cholic acid chelating agent, the cholic acid chelating agent modified by biosterol guanidination has the advantages that the cholic acid binding capacity is high, the food-borne property is strong, the biocompatibility is good, the safety is good, the molecular weight is small, the yield is high, and the side effect is small.

Description

technical field [0001] The invention relates to the technical field of medical small molecule synthesis, in particular to the preparation and application of a novel bile acid chelating agent modified by guanidylation of biological sterols. Background technique [0002] At present, cardiovascular disease has become a major health problem that urgently needs to be solved in the world. Lowering serum cholesterol is of great significance in the prevention and treatment of cardiovascular diseases. Bile salts are hydrophilic and lipophilic molecules that are biosynthesized by cholesterol in the liver and stored in the gallbladder. They promote cholesterol excretion and combine with a large number of bile acids generated by cholesterol metabolism through bile acid chelators. It is an important way to lower cholesterol. Clinically, bile acid chelators such as colestipol and cholestyramine combine with bile acid generated by cholesterol metabolism to promote the excretion of bile ac...

Claims

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Application Information

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IPC IPC(8): C07J41/00C07J75/00A61P3/06A61K31/575
CPCC07J41/0005C07J75/00A61P3/06Y02A50/30
Inventor 陈忠秀李密转汪雷唐逸凡
Owner ZHEJIANG GONGSHANG UNIVERSITY
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