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Matrine derivative and application thereof

A technology of matrine and derivatives, applied in the fields of benzodioxanes, benzene rings, naphthalene rings and indole matrine derivatives, and quinolines, can solve the problem of no antitumor activity, etc. question

Active Publication Date: 2015-09-23
GUANGXI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] There is no related drug that has both the antitumor activity of matrine and the antitumor activity of quinoline, benzodioxane, naphthalene ring, and indole

Method used

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  • Matrine derivative and application thereof
  • Matrine derivative and application thereof
  • Matrine derivative and application thereof

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Experimental program
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Effect test

Embodiment 1

[0029] YFF-1~YFF-9 in general formula I, YFF-10~YFF-15 in general formula II, and YFF-19 quinoline, benzene ring, benzodioxane, naphthalene ring, The preparation method of indole matrine derivatives.

[0030] (1) Preparation of compound YFF-1

[0031] Under nitrogen protection and ice bath conditions, 5 mmol (1.24 g) of matrine was dissolved in 20 mL of anhydrous tetrahydrofuran (THF), and 6 mmol (3 mL) of lithium diisopropylamide (LDA) was injected into In the reaction flask, after stirring and reacting at room temperature for 30 minutes, under ice cooling, add 10 mmol (1.89 g) ethyl indole-2-carboxylate into the flask with a syringe, and stir for 3 hours. Add 10 mL of saturated sodium chloride solution to quench the reaction, extract with chloroform (50 mL x 3), combine the organic phases, dry over anhydrous NaSO4, filter with suction, concentrate the filtrate, and purify by silica gel column chromatography (v methanol:v ethyl acetate Esters = 1:10), and 1.03g of white pow...

Embodiment 2

[0051] The preparation method of the YFF-16~YFF-18 naphthalene ring matrine derivatives in the general formula III.

[0052] (1) Preparation of compound YFF-16

[0053] Add 116 mmol (2.8 g) of sodium hydride and 50 mL of anhydrous tetrahydrofuran into a 100 mL round-bottomed flask, stir well, add 5 mmol (1.24 g) of matrine, slowly raise the temperature to 80°C and add 10 mmol (1.86 g)6 -Methoxy-2-naphthaldehyde, reacted to the end point (TLC detection). After cooling, adjust the reaction solution to neutrality with 3N hydrochloric acid. Extract with dichloromethane (20 mL×3), combine the organic phases, dry over anhydrous NaSO4, filter with suction, and concentrate the filtrate to obtain a yellow oil. Silica gel column chromatography (V methanol: V ethyl acetate = 1:10) purified to obtain 0.81 g of white solid 14-[2-(6-methoxy)naphthylmethylenyl]matrine with a yield of 39%.

[0054] (2) Compounds YFF-17~YFF-18 were prepared according to the method of compound YFF-16.

[00...

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Abstract

The invention discloses a matrine derivative which comprises quinoline, benzene rings, benzdioxan, naphthalene nucleus and indole codonopsine derivatives. The invention further discloses application of the derivative to a preparation method and pharmacy.

Description

technical field [0001] The present invention relates to quinolines, benzene rings, benzodioxanes, naphthalene rings and indole matrine derivatives, and also relates to the preparation method and application of the derivatives in pharmacy. Background technique [0002] Matrine, as one of the alkaloid components in Sophora flavescens, has been found to have a wide range of pharmacological activities. Matrine has good effects on the cardiovascular system, the central nervous system and the digestive system in terms of medical treatment. Such as anti-atherosclerosis, anti-arrhythmia, positive inotropic and anti-hypertensive effects; central inhibitory effects such as sedation, hypnosis, and cooling; anti-gastric mucosa damage, choleretic, antidiarrheal, anti-hepatic damage, etc. Digestive system effect. In terms of anti-tumor, matrine has the effect of directly killing cancer cells. At the same time, it also has certain pharmacological activities such as anti-inflammatory, an...

Claims

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Application Information

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IPC IPC(8): C07D471/22A61K31/4375A61K31/4545A61K31/4709A61P35/00
CPCC07D471/22
Inventor 王立升杨方方梁鹏云周中杰刘华文张森
Owner GUANGXI UNIV
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