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Polymethoxylated flavone derivative with anticancer activity, its pharmaceutical composition, preparation method and application

A technology of polymethoxyflavonoids and derivatives, which is applied in the directions of pharmaceutical combinations, organic active ingredients, medical preparations containing active ingredients, etc., can solve problems such as toxic side effects and poor efficacy, and achieves low side effects and a preparation method. Simple and low cost effect

Inactive Publication Date: 2006-07-19
郭萍
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] In recent years, studies have found that polymethoxyflavones have anticancer effects, among which 3′, 4′, 5,6,7-pentamethoxyflavone or 4′, 5,6,7,8-isopentamethoxyflavone or 3', 4', 5, 6, 7, 8-hexamethoxyflavone or 3, 3', 4', 5, 6, 7, 8-heptamethoxyflavone or their mixtures have the effect of inhibiting the growth of tumor cells However, the poor efficacy and toxic side effects of these compounds limit the clinical application

Method used

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  • Polymethoxylated flavone derivative with anticancer activity, its pharmaceutical composition, preparation method and application
  • Polymethoxylated flavone derivative with anticancer activity, its pharmaceutical composition, preparation method and application
  • Polymethoxylated flavone derivative with anticancer activity, its pharmaceutical composition, preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0093] Example 1: Synthesis of 2'-sulfamoyl-4',5,5',6,7,8-hexamethoxyflavone.

[0094] Add 3', 4', 5,6,7,8-hexamethoxyflavone (800mg) into a three-necked flask, put it in an ice bath, stir, and add HSO dropwise 3 Cl solution 40ml, stirring reaction for 4 hours, control the reaction temperature below 5°C, after the reaction, put the reactant in the refrigerator (2-8°C) overnight, pour the reaction solution into ice water, stir for 10 minutes, filter the precipitated Crystallization, the crystallization was washed with ethyl acetate, the aqueous layer was extracted with ethyl acetate, the combined ethyl acetate was concentrated and dried under reduced pressure, the resulting solid product was combined with the above crystal, dissolved in petroleum ether, and subjected to silica gel column chromatography Separation, eluting with petroleum ether-ethyl acetate (2:1), followed by concentration and drying of the second fraction under reduced pressure, and recrystallization to obtain ...

Embodiment 2

[0095] Example 2: Synthesis of 2'-sulfamoyl-3',4',5,6,7,8-heptamethoxyflavone derivatives.

[0096] Add 3,3',4',5,6,7,8-heptamethoxyflavone (1.02g) into a round bottom flask, add HSO dropwise 3 30ml of Cl solution, stirred and reacted at room temperature for 12 hours. After the reaction was completed, the reaction solution was poured into ice water, extracted 5 times with ethyl acetate, combined with ethyl acetate and concentrated under reduced pressure to obtain a solid, which was dissolved in petroleum ether and coated with alumina Separation by column chromatography, eluting with petroleum ether-ethyl acetate (1:2), collecting the second fraction, concentrating and drying under reduced pressure, and recrystallizing the obtained solid with ether to obtain the intermediate (2′-sulfonyl chloride-3 ', 4', 5,6,7,8-heptamethoxyflavone) 0.82g.

[0097] Put 0.5g of the intermediate into a round bottom flask, add 10ml of dichloromethane to dissolve, stir and add ammonia water (NH ...

Embodiment 3

[0098] Example 3: Synthesis of 3'-sulfamoyl-4',5,6,7,8-pentamethoxyflavone.

[0099] Add 3',5,6,7,8-pentamethoxyflavone (800mg) into a three-necked flask, put it in an ice bath, stir, and add HSO dropwise 3 Cl solution 40ml, stirring reaction for 4 hours, control the reaction temperature below 5°C, after the reaction, put the reactant in the refrigerator (2-8°C) overnight, pour the reaction solution into ice water, stir for 10 minutes, filter the precipitated Crystallization, the crystallization was washed with ethyl acetate, the aqueous layer was extracted with ethyl acetate, the combined ethyl acetate liquid was concentrated and dried under reduced pressure, the resulting solid product was combined with the above crystallization, dissolved in petroleum ether, and analyzed by silica gel column chromatography. Separation of segments, eluting with petroleum ether-ethyl acetate (2:1), followed by concentration and drying of the second fraction under reduced pressure, and recryst...

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Abstract

The disclosed polymethoxyflavone derivative with anticancer activity belongs to the acceptable sodium salt, potassium salt, sulfate, hydrochlorate, halogen compound or ester compound of the compound with general formula shown as (I)~(IV) or itself. This product also has small side effect with low cost.

Description

technical field [0001] The invention belongs to the field of pharmacy, and relates to a polymethoxyflavone derivative with anticancer effect, and also relates to a pharmaceutical composition containing the derivative, a preparation method thereof and an application in pharmacy. Background technique [0002] Polymethoxylated flavones exist in a variety of natural plants and have high medicinal value. [0003] In recent years, studies have found that polymethoxyflavones have anticancer effects, among which 3′, 4′, 5,6,7-pentamethoxyflavone or 4′, 5,6,7,8-isopentamethoxyflavone or 3', 4', 5, 6, 7, 8-hexamethoxyflavone or 3, 3', 4', 5, 6, 7, 8-heptamethoxyflavone or their mixtures have the effect of inhibiting the growth of tumor cells However, the poor efficacy and toxic side effects of these compounds limit their clinical application. And their structurally modified partial derivatives also have inhibitory effect, and the drug effect is increased and the toxic and side effec...

Claims

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Application Information

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IPC IPC(8): C07D311/30A61K31/352A61K9/08A61K9/20A61K9/48A61K9/14A61K9/06A61P35/00
Inventor 郭萍周自桂董云发李兆龙郭彦飞潘毅李玉峰卜清明
Owner 郭萍
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