Celastrol derivative and preparation method thereof and application of celastrol derivative to preparation of antitumor medicine

A technology of triptolide and triptolide ester is applied in the application field of triptolide derivatives in the treatment and preparation of antitumor drugs, and can solve the problem of finished medicines without taking relevant consideration and ignoring the water solubility of triptolide problems, etc., to achieve the effect of being conducive to quality control, improving pharmacokinetic properties, and improving water solubility

Active Publication Date: 2012-05-02
ZHEJIANG UNIV OF TECH
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The Chinese patent with publication number CN 101311187A discloses a long-chain alcohol ester of tripterygium wilfordii and its preparation

Method used

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  • Celastrol derivative and preparation method thereof and application of celastrol derivative to preparation of antitumor medicine
  • Celastrol derivative and preparation method thereof and application of celastrol derivative to preparation of antitumor medicine
  • Celastrol derivative and preparation method thereof and application of celastrol derivative to preparation of antitumor medicine

Examples

Experimental program
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Example Embodiment

[0032] Example 1: Synthesis of Tripterygium Wilfordii Derivative CLS-1 (the synthetic route is shown in Figure 1)

[0033] Dissolve 72.8mg triphosgene (BTC) (0.24mmol) in 2mL dichloromethane (DCM), add 1mL morpholine (0.35mmol) dichloromethane solution with a concentration of 0.35mol / L and 100μL triethyl dropwise under ice bath Amine (0.99mmol), stirred at room temperature for 1h, and then 1mL of 0.2mol / L triptorubin (0.2mmol) dichloromethane solution was added dropwise, stirring was continued for 24h, the reaction was stopped, 15mL of deionized water and ethyl acetate were added Extract 4mL*3 times, combine the organic layers, wash with saturated NaCl solution 4mL*3 times, anhydrous Na 2 SO 4 Dry, filter with suction and concentrate the filtrate to obtain a dark red oily crude product. Then the crude extract is eluted by flash column chromatography with a mixed solvent of n-hexane: acetone with a volume ratio of 3:1 as the eluent. Detection (developing solvent petroleum ether: a...

Example Embodiment

[0038] Example 2 Synthesis of Tripterygium Wilfordii Derivatives CLS-2 (Synthetic route diagram is shown in Figure 1)

[0039] Dissolve 72.8mg BTC (0.24mmol) in 2mL dichloromethane (DCM), add 1mL 0.35mol / L N-methylpiperazine (0.35mmol) dichloromethane solution and 100μL triethyl dropwise under ice bath Amine (0.99mmol), stirred at room temperature for 1h, then add 1mL of 0.2mol / L triptorubin (0.2mmol) dichloromethane solution, continue stirring for 24h, stop the reaction, add 15mL deionized water, and extract with ethyl acetate 4mL*3 times, combine the organic layers, wash with saturated NaCl solution 4mL*3 times, anhydrous Na 2 SO 4 Dry, filter with suction, and concentrate to obtain a dark red oily crude product. Then, the crude extract is eluted by fast column chromatography with a mixed solvent of n-hexane: acetone with a volume ratio of 3:1 as the eluent, and spot plate detection ( Developing solvent petroleum ether: acetone=2:1; Rf value 0.30), collect the eluent containing...

Example Embodiment

[0040] Example 3 Synthesis of Tripterygium Wilfordii Derivatives CLS-3 (Synthetic route diagram is shown in Figure 1)

[0041] Dissolve 72.8mg triphosgene BTC (0.24mmol) in 2mL dichloromethane (DCM), add 1mL 0.35mol / L N-ethylpiperazine (0.35mmol) dichloromethane solution and 100μL dropwise under ice bath Triethylamine, stir at room temperature for 1 hour, then add 1 mL of 0.2 mol / L triptoene (0.2 mmol) dichloromethane solution, continue to stir for 24 hours, then stop the reaction, add 15 mL deionized water, and extract 4 mL with ethyl acetate *3 times, combine the organic layers, wash 4mL with saturated NaCl solution *3 times, anhydrous Na 2 SO 4 Dry, filter with suction, and concentrate to obtain a dark red oily crude product. Then, the crude extract is eluted by fast column chromatography with a mixed solvent of n-hexane: acetone with a volume ratio of 3:1 as the eluent, and spot plate detection ( Developing solvent petroleum ether: acetone = 2:1; Rf value 0.33), collect the e...

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Abstract

The invention relates to celastrol, a celastrol derivative, a method for preparing the celastrol derivative, biogenetic salt prepared from the celastrol derivative serving as a raw material, and application of the celastrol derivative to the preparation of an antitumor medicine. The celastrol derivative has a structure shown as a formula I, wherein R1 is H, C1-C6 straight-chain or branched-chain alkyl, benzyl and benzyl with a substituent group on a benzene ring; and R2 or R3 are independent C5-C6 cyclic hydroxyl, C1-C6 chain alkyl, phenyl and substituted phenyl respectively, or R2 and R3 are cyclized with N, and the cycle is hexahydric cyclic heterocycle containing N or O. The celastrol derivative has high antitumor activity, stability and water solubility. The celastrol derivative can be salified with one of medically acceptable inorganic acids (such as hydrochloric acid, sulfuric acid and phosphoric acid) or organic acids (citric acid, cinnamic acid, succinic acid and the like); and the salt has high water solubility.

Description

(1) Technical field [0001] The present invention relates to the preparation method of tripterygne and its derivatives and tripteryne derivatives, also relates to the biological salt prepared from tripteryne derivatives as raw materials, and tripteryne derivatives in the preparation of anti-tumor drugs in the application. (2) Background technology [0002] Malignant tumors seriously endanger people's health. According to WHO statistics, among the more than 5 billion people in the world, 6.9 million people die from malignant tumors every year on average, and 8.7 million new cases occur, and the number is still increasing year by year. Antineoplastic drug therapy is one of the main methods of cancer treatment. Natural products are a treasure trove for discovering new antineoplastic drugs. The lead compounds of many antineoplastic drugs are obtained from nature, such as vinblastine, vincristine, camptothecin, Paclitaxel, etc., but these natural compounds often require structura...

Claims

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Application Information

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IPC IPC(8): C07J63/00A61P35/00A61P1/16
Inventor 单伟光占扎君张丽雯温彦涛陈艳王建伟唐岚于海宁侯晓蓉
Owner ZHEJIANG UNIV OF TECH
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