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Acylated derivative of genistein and preparation process of acylated derivative

A technology of genistein and preparation process, which is applied in the field of pharmaceutical products, can solve the problems of no structural modification reports, etc., and achieve the effects of convenient mass production and application, simple operation, and low cost

Inactive Publication Date: 2018-01-12
荆门医药工业技术研究院
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0010] A kind of acylated derivative of genistein among the present invention is to synthesize a kind of new acylated derivative by chloroacetyl chloride and genistein under the action of catalyst, has better solubility in water, can improve Its absorption rate and bioavailability in the body, and it has a good inhibition rate on liver cancer cell HepG2, and it is expected to develop a new drug with anti-tumor effect. At present, there is no report on the similar structural modification of genistein

Method used

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  • Acylated derivative of genistein and preparation process of acylated derivative
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  • Acylated derivative of genistein and preparation process of acylated derivative

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Embodiment 1

[0031] Weigh 20g of genistein, put it into a 500ml three-neck round bottom flask, use 300ml tetrahydrofuran as a solvent, and add triethylamine dropwise to adjust the pH to about 5-7. Weigh 8.36 g of chloroacetyl chloride, dissolve it in 50 ml of tetrahydrofuran, and drop into the reaction solution at a rate of 6-10 drops per minute with a constant pressure dropping funnel. The reaction temperature was controlled at 0-5°C and monitored by thin-layer chromatography. After the reaction was completed, it was vacuum-filtered and vacuum-dried at 40°C.

Embodiment 2

[0033] Weigh 19g of genistein, put it into a 500ml three-neck round bottom flask, use 200ml of dichloromethane as solvent, and add triethylamine dropwise to adjust the pH to about 5-7. Weigh 9.36 g of chloroacetyl chloride, dissolve it in 45 ml of dichloromethane, and drop into the reaction solution at a rate of 6-10 drops per minute with a constant pressure dropping funnel. The reaction temperature was controlled at 0-5°C and monitored by thin-layer chromatography. After the reaction was completed, it was filtered with suction and dried under vacuum at 40°C.

Embodiment 3

[0035] Weigh 21g of genistein, put it into a 500ml three-neck round bottom flask, use 250ml dichloroethane as solvent, and add triethylamine dropwise to adjust the pH to about 5-7. Weigh 9.5 g of chloroacetyl chloride, dissolve in 40 ml of dichloroethane, and drop into the reaction solution at a rate of 6-10 drops per minute with a constant pressure dropping funnel. The reaction temperature was controlled at 0-5°C and monitored by thin-layer chromatography. After the reaction was completed, it was filtered with suction and dried under vacuum at 40°C.

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Abstract

The invention discloses a preparation process of an acylated derivative of genistein. The preparation process comprises the following process steps: (1) taking genistein, dissolving the genistein in an organic solvent, dripping a catalyst, controlling the pH value to be 2-7, and controlling the temperature of the solution to be 0-5 DEG C; (2) dissolving chloroacetyl chloride into the organic solvent, adding into a constant pressure funnel, dripping into the solution in (1), and producing solids after dripping; monitoring the reaction process by TLC (Thin-Layer Chromatography), raising the temperature to be 10 DEG C, continuously reacting, and stopping the reaction within 17 hours; (3) standing the reaction solution for an hour, performing suction filtration, performing vacuum drying on thefilter cake at the temperature of 40 DEG C, thereby obtaining the acylated derivative of genistein. The preparation process has the advantages that the compound has excellent solubility in water, thein-vivo oavailability of the compound can be greatly improved, the compound has excellent inhibition rate on hepatoma carcinoma cell HepG2, and a novel drug with excellent water solubility and an anti-tumor effect is expected to be developed.

Description

technical field [0001] The invention relates to the technical field of pharmaceutical products, in particular to an acylated derivative of genistein and a preparation process thereof. Background technique [0002] Genistein, also known as genistein, genistein, and 5,7,4′-trihydroxyisoflavone, is mainly obtained from soybean, clover, kudzu root, sophora japonica, sophora japonica, genistein The active ingredient extracted from leguminous plants such as bean flower) and broad bean root is a natural tyrosine kinase and soybean metabolite, known as phytoestrogens. Genistein is one of the most active and functional isoflavones. It is a single component and a non-estrogen compound. It has dual estrogen and anti-estrogen regulation effects. It is also widely used in pharmaceuticals and health products. field. According to research, genistein has the following effects: [0003] (1) Having estrogenic and anti-estrogenic properties; [0004] (2) It has anti-oxidation effect; [0...

Claims

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Application Information

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IPC IPC(8): C07D311/36A61P35/00
Inventor 杨成雄何佳丽李立威毛学荣
Owner 荆门医药工业技术研究院
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