A kind of tripterine derivative and its preparation method and application

A technology of tripteryglide and its derivatives, which is applied in the direction of medical formulas, drug combinations, steroids, etc., can solve the problems of tripterygine's insufficient druggability, no significant improvement in anti-tumor activity, etc., and achieve the reduction of cytotoxic activity , Increase the effect of water solubility

Active Publication Date: 2021-08-24
ZHEJIANG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] At present, domestic and foreign patent research is mainly to form an ester bond and an amide bond at the 29-position carboxyl group of tripteryglide, but this does not significantly improve its anti-tumor activity, nor does it change the current situation of tripteryglide's lack of druggability

Method used

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  • A kind of tripterine derivative and its preparation method and application
  • A kind of tripterine derivative and its preparation method and application
  • A kind of tripterine derivative and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] Embodiment 1: the synthesis of tripterine derivative Ia

[0033]

[0034] Methanol (4mL) and tripterine (45.0mg, 0.1mmol) were added to a 25mL two-neck flask, and hydrochloric acid (1mL) at pH=1 was added with stirring at room temperature, and the pH of the reaction solution was=1-2. React at room temperature for 12 hours, add glycine (15.0mg, 0.2mmol), add sodium carbonate to adjust pH = about 8, continue to react for 8 hours, TLC detection, after the reaction, add water (5mL), stir to dissolve the sodium carbonate solid, Add hydrochloric acid to make the pH of the reaction solution around 7, extract three times with ethyl acetate (10 mL), combine the organic phases, wash twice with saturated brine, dry over anhydrous magnesium sulfate, then suction filter, and concentrate the filtrate to dryness to obtain crude product. The crude product was separated and purified by flash column chromatography (petroleum ether: ethyl acetate = 6:1), and the product was vacuum-dri...

Embodiment 2

[0037] Embodiment 2: the synthesis of tripterine derivative Ib

[0038]

[0039] Methanol (4mL) and tripterine (45.0mg, 0.1mmol) were added to a 25mL two-necked bottle, and hydrochloric acid (1mL) with pH=1 was added under stirring at room temperature, and the pH of the reaction solution was about 1-2. React at room temperature for 12 hours, add alanine (17.8mg, 0.2mmol), add sodium carbonate to adjust pH=8, continue to react for 8 hours, TLC detection, after the reaction, add water (5mL), stir to dissolve sodium carbonate solid, add hydrochloric acid to make the pH of the reaction solution around 7, extract three times with ethyl acetate (10 mL), combine the organic phases, wash with saturated brine, and then dry with anhydrous magnesium sulfate, then suction filter, and the filtrate is concentrated to dryness to obtain crude product. The crude product was separated and purified by flash column chromatography (petroleum ether: ethyl acetate = 6:1), and the product was vac...

Embodiment 3

[0042] Embodiment 3: the synthesis of tripterine derivative Ic

[0043]

[0044] Methanol (4mL) and tripterine (45.0mg, 0.1mmol) were added to a 25mL two-necked bottle, and hydrochloric acid (1mL) with pH=1 was added under stirring at room temperature, and the pH of the reaction solution was about 1-2. React at room temperature for 12 hours, add valine (23.4mg, 0.2mmol), add sodium carbonate to adjust pH=7, continue to react for 8 hours, TLC detection, after the reaction, add water (5mL), stir to dissolve sodium carbonate solid, add hydrochloric acid to make the pH of the reaction solution = about 7, extract three times with ethyl acetate (10 mL), combine the organic phases, wash twice with saturated brine, dry over anhydrous magnesium sulfate, and then filter with suction, and concentrate the filtrate to dryness to obtain crude product. The crude product was separated and purified by flash column chromatography (petroleum ether: ethyl acetate = 6:1), and the product was v...

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Abstract

The invention provides a tripteryne derivative shown in formula (I), the preparation method of which is: dissolving tripteryne (II) in methanol, adjusting the pH=1-2, stirring and reacting at room temperature for 8-16h , to obtain a reaction solution containing the intermediate (III); add amino acid (IV) to the reaction solution, adjust the pH=7-8, stir and react at room temperature for 8-16h, and then the reaction solution is post-treated to obtain the formula (I) The shown product; tripterine derivatives of the present invention can be applied to the preparation of antitumor drugs.

Description

technical field [0001] The invention relates to a tripterine derivative, a preparation method thereof, and an application in the preparation of antitumor drugs. Background technique [0002] Natural products are an important source for the prevention and treatment of human diseases. About 30% of the chemical drugs currently on the market are derived from natural products, and some drugs are produced with natural products as lead compounds through structural modification and structural modification. Celastrol, also known as celastrol, is a natural product with a variety of biological activities, derived from the root bark of the traditional Chinese medicine Tripterygium wilfordii, and is a red crystalline powder of triterpenoids. Tripteryglide, as a natural product with multiple activities, has certain clinical application prospects, but its application is limited due to its high toxicity and low bioavailability. Among the many activities of tripterine, the anti-tumor activi...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07J71/00A61K31/58A61P35/00
CPCA61P35/00C07J71/0063
Inventor 王建伟金成庆占扎君单伟光伍海彬
Owner ZHEJIANG UNIV OF TECH
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