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Podophyllotoxin heterocyclic lipid derivatives, and synthetic method and application thereof

A technology of podophyllotoxin and derivatives, applied in drug combination, organic chemistry, antineoplastic drugs, etc., can solve the problems of low water solubility, toxic and side effects, etc., and achieve the effect of low toxic and side effects and obvious tumor cell inhibitory activity

Inactive Publication Date: 2015-04-29
JIANGSU UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] Since podophyllotoxin is a fat-soluble natural product, there is a problem of low water solubility, and in subsequent studies, it was found that podophyllotoxin has toxic and side effects and other shortcomings

Method used

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  • Podophyllotoxin heterocyclic lipid derivatives, and synthetic method and application thereof
  • Podophyllotoxin heterocyclic lipid derivatives, and synthetic method and application thereof
  • Podophyllotoxin heterocyclic lipid derivatives, and synthetic method and application thereof

Examples

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Embodiment 1

[0018] Example 1: Preparation of Podophyllotoxin Heterocyclic Lipid Derivatives

[0019] At room temperature, add podophyllotoxin, corresponding heterocyclic acid, refined dichloromethane and catalyst to a 50mL Erlenmeyer flask in sequence, the reaction is complete as detected by TLC, and the corresponding podophyllotoxin heterocyclic lipid derivatives are obtained by column chromatography. Dissolve 50mmol of podophyllotoxin and 50mmol of 2-indolecarboxylic acid in 20mL of dichloromethane, and continue to add 5%-10% of the reaction system weight N,N-dicyclohexylcarbodiimide and 4-diaminopyridine, TLC follow-up detection generates corresponding ester derivatives, add 1-1.5 times of the product weight of gel to concentrate the solvent under reduced pressure, and use dichloromethane: acetone volume ratio=100: 1 column chromatography to obtain the corresponding of podophyllotoxin ester derivatives.

[0020] Compound 1: 1 H NMR (300MHz, CDCl 3 )δ: 9.03(s, 1H), 7.69(d, J=8.1Hz, 1...

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Abstract

The invention relates to podophyllotoxin heterocyclic lipid derivatives, and a synthetic method and an application thereof. In the invention, compared with podophyllotoxin, the obtained podophyllotoxin heterocyclic lipid derivatives have obvious tumour cell inhibitory activities; the inhibitory activities of a part of novel compounds to tumour cell lines are obviously superior to that of parent molecule podophyllotoxin; furthermore, the toxic and side effects are low; and for example, the IC50 value in the background technical literature is 4.0 mu M, but the IC50 value in the experiments in the invention achieves 1.93 mu M.

Description

technical field [0001] The invention belongs to the technical field of chemical pharmacy, and specifically relates to a heterocyclic lipid derivative of podophyllotoxin, a preparation method thereof, and an application in the preparation of tumor suppressor drugs. Background technique [0002] Podophyllotoxin (PPT) is a lignans compound with natural activity. In recent years, many studies have shown that podophyllotoxin is a very important lead compound of anti-tumor drugs. The anti-tumor activity of its derivatives has been in the spotlight. For example, Toward synthesis of third-generation spin-labeled podophyllotoxin derivatives using isocyanides multicomponent reactions published in the 75th issue of European Journal of Medicinal Chemistry, P228-288, by Liang Kou et al. Podophyllotoxin derivatives) article shows that podophyllotoxin derivatives modified with podophyllotoxin skeleton have significantly better inhibitory effect on DNA topoisomerase II than podophyllotoxin...

Claims

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Application Information

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IPC IPC(8): C07D493/04A61K31/381A61K31/404A61K31/366A61P35/00
CPCC07D493/04
Inventor 赵卫国王小明韩洪苇周宏
Owner JIANGSU UNIV OF SCI & TECH
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