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Theasapogenol derivative with anti-HIV (Human Immunodeficiency Virus) activity, preparation method and application thereof

A technology of tea saponin and derivatives, which is applied in the field of medicine to achieve the effects of high anti-HIV activity, easy control of reaction conditions, and high product purity

Inactive Publication Date: 2011-04-27
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] Tea saponins can be obtained from tea saponins after hydrolysis. Their structures are pentacyclic triterpene chemicals, and their basic skeleton is similar to that of oleanolic acid. However, there is no report on its use in anti-HIV experiments

Method used

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  • Theasapogenol derivative with anti-HIV (Human Immunodeficiency Virus) activity, preparation method and application thereof
  • Theasapogenol derivative with anti-HIV (Human Immunodeficiency Virus) activity, preparation method and application thereof
  • Theasapogenol derivative with anti-HIV (Human Immunodeficiency Virus) activity, preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] Embodiment 1: Synthetic compound shown in formula II

[0033] (1) Get tea presapogenol-A (5g, about 8.9mmol) and 50mlDMF (dimethylformamide) and mix, stir and dissolve; add TrCl (trityl chloride 18mmol) reaction under the protection of argon, Then slowly add DMAP (1.2 g about 10 mmol) to catalyze the reaction, and react at 60° C. for 2 hours. After the reaction was completed, the mixture was diluted with water, and ethyl acetate was added for extraction. The organic phase was dried with anhydrous magnesium sulfate, filtered, and distilled under reduced pressure to obtain the crude product a1 with a conversion rate of 98%. The crude product was used in the next reaction without purification.

[0034] (2) Dissolve a1 (7.3g, about 8.7mmol) and anhydrous pyridine (50ml), then add 10ml of acetic anhydride, slowly add DMAP (1.2g, about 10mmol), and stir the mixture at room temperature overnight. It was then frozen to 0°C and 1N HCl (25ml) was added. Extracted 3 times with...

Embodiment 2

[0043] Embodiment 2: Synthetic compound shown in formula III

[0044] (1) a4 (1.5g about 2mmol) and anhydrous CH 2 Cl 2(20ml) mixed, stirred to dissolve, added EDC (3mmol) and HOBT (3mmol), then added L-leucine methyl ester (2.5mmol) to the solution, stirred overnight, the solution was washed with CH 2 Cl 2 (50ml) extract, CH 2 Cl 2 Layer was washed three times with water (50ml), washed with anhydrous MgSO 4 Dry, filter to remove anhydrous sodium sulfate, and concentrate under reduced pressure to obtain a crude product, which is purified by silica gel column chromatography, and finally crystallized with ethyl acetate and n-butane to obtain b1 with a yield of 96%.

[0045] (2) Dissolve b1 (1.2g about 1mmol), MeOH (4ml) and THF (4ml), and add 4N NaOH (2ml) to the solution. After the reaction is complete, the mixture is acidified to pH 4 with hydrochloric acid, and then washed with chloroform Extract three times (3×50ml) with anhydrous MgSO 4 Dry, filter to remove anhydrou...

Embodiment 3

[0049] Embodiment 3: Synthesis of compounds shown in formula IV

[0050] (1) a4 (1.5g about 2mmol) and anhydrous CH 2 Cl 2 (20ml) were mixed, stirred to dissolve, EDC (3mmol) and HOBT (3mmol) were added, and then 4S-(8-aminooctylamide)-3R-hydroxyl-6-methylheptanoic acid benzyl ester (1.6 mmol), stirred overnight, the solution with CH 2 Cl 2 (50ml) extract, CH 2 Cl 2 Layer was washed three times with water (50ml), washed with anhydrous MgSO 4 Dry, filter to remove anhydrous sodium sulfate, and concentrate under reduced pressure to obtain a crude product, which is purified by silica gel column chromatography, and finally crystallized with ethyl acetate and n-butane to obtain c1 with a yield of 96%.

[0051] (2) Dissolve c1 (0.5g about 1mmol), MeOH (4ml) and THF (4ml), and add 4N NaOH (2ml) to the solution. After the reaction is complete, the mixture is acidified to pH 4 with hydrochloric acid, and then washed with chloroform Extract three times (3×50ml) with anhydrous MgS...

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Abstract

The invention discloses a theasapogenol derivative with anti-HIV (Human Immunodeficiency Virus) activity, a preparation method and application thereof. The theasapogenol derivative with anti-HIV activity has a structure disclosed as a formula I. The preparation method comprises the following steps of: (1) reacting the 4-dimethylaminopyridine with trityl chloride to obtain a compound a1, wherein theasapogenol as a raw material, and 4-dimethylaminopyridine is used as a catalyst in a pyridine solvent; (2) reacting the a1 with acetic anhydride by using the dimethylaminopyridine as the catalyst inan anhydrous pyridine solvent and adding sulfanilic acid pyridinium into a solution for reaction to obtain a compound a2; (3) oxidizing the a2 by using pyridinum chlorochromate salt to obtain a compound a3; (4) oxidizing the a3 by using NaClO2 and NaH2PO4 to obtain a4; and (5) hydrolyzing the a4 by using an aqueous solution of methanol and sodium hydroxide to obtain the theasapogenol derivative with anti-HIV activity disclosed as the formula I. The theasapogenol derivative has the advantages of high anti-HIV activity, simple preparation technology, high product purity, easy control of reaction conditions and industrial production.

Description

technical field [0001] The invention relates to the field of medicine, in particular to a teasapogenin derivative with anti-HIV activity and a preparation method and application thereof. Background technique [0002] Since AIDS was discovered clinically in 1981, it has spread extremely fast. About 2.1 million people die from AIDS every year, and 2.5 million people are newly infected with AIDS. However, so far, AIDS is still an incurable fatal infectious disease. How to find a drug that can effectively suppress HIV has become the biggest problem facing medical workers in the world today. [0003] Traditional anti-AIDS drugs are HIV protease, integrase and reverse transcriptase inhibitors, but they have low bioavailability, strong side effects, and easy to develop drug resistance. Searching for anti-AIDS active compounds from natural products has become an important direction of anti-AIDS research. [0004] Among natural compounds, triterpenoids have shown excellent anti-HIV...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07J63/00A61K31/56A61P31/18
Inventor 叶勇王延芳
Owner SOUTH CHINA UNIV OF TECH
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