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Genistein derivative and preparation method and application thereof

A technology of genistein and its derivatives, which is applied in the direction of drug combinations, pharmaceutical formulas, and medical preparations containing active ingredients, etc., can solve the problems of high toxicity and side effects and limitations of bone marrow suppression, and achieve good bioavailability, low side effects, good solubility effect

Active Publication Date: 2018-04-10
JINGCHU UNIV OF TECH +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0010] 5-Fluorouracil is an anticancer drug widely used clinically, but its practical application is limited because of its gastrointestinal reactions, bone marrow suppression and other side effects.

Method used

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  • Genistein derivative and preparation method and application thereof
  • Genistein derivative and preparation method and application thereof
  • Genistein derivative and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] A preparation method of genistein derivatives, comprising the steps of:

[0033] (1) Synthesis of 5-fluorouracil-1-acetic acid: at first, add 1.6g 5-fluorouracil and 30ml of alkaline aqueous solution of 10wt% in the three-necked flask that is equipped with reflux condenser and magnetic force stirring, then slowly add to the three-necked flask Add 4ml of 0.525g / mL chloroacetic acid solution dropwise. After the dropwise addition, heat and stir in a water bath at 60°C for 5 hours. After the reaction, cool the reaction solution to room temperature, adjust the pH value to 2, and then place it in a refrigerator at 4°C to cool overnight. , suction filtration, and drying to obtain needle-like crystal 5-fluorouracil-1-acetic acid, the specific reaction formula is as follows:

[0034]

[0035] (2) Preparation of genistein derivatives: take 0.5 g of 5-fluorouracil-1-acetic acid prepared in the above step (1) in a three-necked flask, then add 0.6 g of genistein, 0.6 g of catalys...

Embodiment 2

[0038] A preparation method of genistein derivatives, comprising the steps of:

[0039] (1) Synthesis of 5-fluorouracil-1-acetic acid: at first, add 1.6g 5-fluorouracil and 40ml of alkaline aqueous solution of 10wt% in the three-necked flask that is equipped with reflux condenser and magnetic force stirring, then slowly add to the three-necked flask Add 4ml of 0.65g / mL chloroacetic acid solution dropwise. After the dropwise addition, heat and stir in a water bath at 60°C for 5 hours. After the reaction, cool the reaction solution to room temperature, adjust the pH value to 2, and then place it in a refrigerator at 4°C to cool overnight. , suction filtration, and drying to obtain needle-like crystal 5-fluorouracil-1-acetic acid, the specific reaction formula is as follows:

[0040]

[0041] (2) Preparation of genistein derivatives: Take 0.5 g of 5-fluorouracil-1-acetic acid prepared in the above step (1) in a three-necked flask, then add 1.1 g of genistein, 1.0 g of catalyst...

Embodiment 3

[0044] A preparation method of genistein derivatives, comprising the steps of:

[0045] (1) Synthesis of 5-fluorouracil-1-acetic acid: at first, add 1.6g 5-fluorouracil and 30ml of alkaline aqueous solution of 10wt% in the three-necked flask that is equipped with reflux condenser and magnetic force stirring, then slowly add to the three-necked flask Add 4ml of 0.75g / mL chloroacetic acid solution dropwise. After the dropwise addition, heat and stir in a water bath at 60°C for 5 hours. After the reaction, cool the reaction solution to room temperature, adjust the pH value to 2, and then place it in a refrigerator at 4°C to cool overnight. , suction filtration, and drying to obtain needle-like crystal 5-fluorouracil-1-acetic acid, the specific reaction formula is as follows:

[0046]

[0047] (2) Preparation of genistein derivatives: Take 0.45 g of 5-fluorouracil-1-acetic acid prepared in the above step (1) in a three-necked flask, then add 0.6 g of genistein, 0.6 g of catalyst ...

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Abstract

The invention discloses a genistein derivative and a preparation method and application thereof. The preparation method includes the process steps of (1) synthesis of 5-fluorouracil-1 acetic acid, wherein 5-fluorouracil reacts with chloroacetic acid in an aqueous alkali solution to generate the 5-fluorouracil-1-acetic acid; (2) preparation of the genistein derivative, wherein 5-fluorouracil-1-acetic acid and genistein are dissolved in an organic solvent, a catalyst is added for reaction, the product is filtered and the filter cake is dried to prepare a new genistein derivative. The derivativehas good solubility in organic solvents, also has a good inhibition rate on liver cancer cell HepG2 and ovarian cancer cell line SKOV-3, and is expected to develop a new drug with an anti-tumor effect.

Description

technical field [0001] The invention belongs to the technical field of medical products, and in particular relates to a genistein derivative, a preparation method thereof and an antitumor application. Background technique [0002] Genistein, also known as genistein, genistein, 5,7,4′-trihydroxy isoflavone, is mainly obtained from soybean, clover, kudzu root, sophora japonica, sophora japonica, genistein It 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) Estrogenic and anti-estrogenic properties [0004] (2) Has antioxidant effect [0005] (3) Can inhibit the activity of protein tyrosine kinase (PTK) [0006] (4) Can inhibit t...

Claims

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Application Information

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IPC IPC(8): C07D405/12A61K31/513A61P35/00
CPCC07D405/12
Inventor 杨成雄张永琴李立威毛学荣
Owner JINGCHU UNIV OF TECH
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