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Water-soluble triptolide derivative and preparation method and application thereof

A technology of triptolide and its derivatives, applied in the field of medicine, can solve the problems of triptolide's poor water solubility, limited research and development, narrow therapeutic window, etc., and achieve the goals of improving water solubility, facilitating salt formation, and reducing toxic and side effects Effect

Active Publication Date: 2019-07-12
HUBEI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Triptolide has poor water solubility, narrow therapeutic window, and has relatively large toxic and side effects on the digestive system, genitourinary system, and blood system, which limits its clinical research and development.

Method used

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  • Water-soluble triptolide derivative and preparation method and application thereof
  • Water-soluble triptolide derivative and preparation method and application thereof
  • Water-soluble triptolide derivative and preparation method and application thereof

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Experimental program
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Effect test

Embodiment 1

[0038] The preparation method of the water-soluble triptolide derivative of the present embodiment specifically comprises the following steps:

[0039]

[0040] (1) After mixing 1.0g (6.58mmol) of hydroquinone and 0.54g (7.50mmol) of acrylic acid, add it to 10mL of methanesulfonic acid at one time, heat and stir at 70°C for 18h, TLC detects that the reaction is complete, stop stirring, and add 125mL of water, It was extracted with ethyl acetate successively, washed with pure water, saturated aqueous sodium bicarbonate solution and saturated brine, dried over anhydrous sodium sulfate, and evaporated to dryness under reduced pressure. Recrystallized from chloroform-n-hexane to obtain a yellow solid compound XC-01 with a yield of about 67%. [M+H] + :221.0; 1 H NMR, 600MHz (CDCl 3 )δ6.45(q,1H), 3.04(s,2H), 1.96(m,3H), 1.92(m,3H), 1.41(s,6H).

[0041]

[0042] (2) 1.1g (5mmol) of the compound of step (1) was dissolved in 40mL of acetic acid solution; 0.57mL (11mmol) of br...

Embodiment 2

[0062] The preparation method of the water-soluble triptolide derivative of the present embodiment specifically comprises the following steps:

[0063] (1) For every 1.0g (6.58mmol) of hydroquinone, mix with 0.85g (7.50mmol) of 3-methyl-2-butenoic acid and add to 10mL methanesulfonic acid at one time, heat and stir at 70°C for 4h, TLC Check that the reaction is complete, stop stirring, add 125mL of water, extract with ethyl acetate successively, wash with water, saturated aqueous sodium bicarbonate solution and saturated brine, dry over anhydrous sodium sulfate, evaporate to dryness under reduced pressure, and recrystallize with chloroform-n-hexane to obtain yellow solid. [M+H] + :221.0; 1 H NMR, 600MHz (CDCl 3 )δ6.45(q,1H), 3.04(s,2H), 1.96(m,3H), 1.92(m,3H), 1.41(s,6H).

[0064] (2) 6.6g (30mmol) of the compound in step (1) was dissolved in 200mL of acetic acid solution; 3.4mL (66mmol) of bromine water was added dropwise to the above solution and stirred at room temperat...

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PUM

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Abstract

The invention discloses a water-soluble triptolide derivative and a preparation method and application thereof. The chemical structural formula of the water-soluble triptolide derivative is as shown in the specification, wherein n=2,3,4..., and n is a positive integer greater than 1. Under the precondition of maintaining biological activity of triptolide, water solubility of the compound is enhanced, and toxic and side effect of triptolide is improved. Thereby, triptolide can be safely and effectively applied in clinic.

Description

technical field [0001] The invention relates to the technical field of medicine, in particular to a water-soluble triptolide derivative and its preparation method and application. Background technique [0002] Triptolide, also known as triptolide, is an epoxy diterpene lactone compound isolated from the Euonymus family Tripterygium genus. It is the main active ingredient of the traditional Chinese medicine plant Tripterygium wilfordii. It has anti-inflammatory, immune Inhibition, anti-fertility and anti-tumor effects. The antitumor effect of triptolide has attracted widespread attention. At low concentrations (~nM), triptolide can not only inhibit tumor growth, but also enhance the antitumor effects of various chemotherapy drugs. Triptolide has poor water solubility, narrow therapeutic window, and has relatively large toxic and side effects on the digestive system, genitourinary system, and blood system, which limits its clinical research and development. Contents of the...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07J73/00A61P35/00A61K31/585
CPCC07J73/003A61P35/00
Inventor 彭志红刘媚琳杜茜杨雁羽宋蔚陈勇
Owner HUBEI UNIV
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