7,4',5'-trihydroxyflavanone derivative and its application in preparation of liver cancer treatment medicines

A trihydroxyflavone, a technology for treating liver cancer, applied in the field of medicine, can solve the problems of poor selectivity, strong toxic and side effects, easy to produce drug resistance and the like

Inactive Publication Date: 2013-09-04
SHAANXI UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In order to overcome the shortcomings of traditional cytotoxic drugs such as poor selectivity, strong side effects, and easy drug resistance, anti-tumor drugs have transitioned from the research of traditional cytotoxic drugs to the development of drugs that specifically act on abnormal cells based on a clear mechanism of action.

Method used

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  • 7,4',5'-trihydroxyflavanone derivative and its application in preparation of liver cancer treatment medicines
  • 7,4',5'-trihydroxyflavanone derivative and its application in preparation of liver cancer treatment medicines
  • 7,4',5'-trihydroxyflavanone derivative and its application in preparation of liver cancer treatment medicines

Examples

Experimental program
Comparison scheme
Effect test

Embodiment I-01

[0016] Example I-01: Synthesis of 2-(3,4-dihydroxy)-2,7-dihydroxy-5-methoxy-4H-benzopyran-4-one

[0017]

[0018] Under nitrogen protection conditions, 2-(3,4-dihydroxy)3,5,7-trihydroxy-4H-benzopyran-4-one (1g, 3.31mmol), benzyl bromide (1.98g, 11.58 mmol), potassium carbonate (1.60g, 11.58mmol) and 20mL of N,N-dimethylformamide were placed in a 100mL round bottom flask, and after stirring at room temperature for 12h, 100mL of water was added to the reaction system. Then it was extracted with ethyl acetate (100 mL×3), and the organic layers were combined. The organic phase was washed with saturated brine, dried over anhydrous sodium sulfate, and the organic phase was concentrated in vacuo. The residue was purified by silica gel column chromatography using chloroform as the eluent to obtain 450 mg of a yellow powdery solid with a yield of 21%.

[0019] 3,7-bis(benzyloxy)-2-[3,4-bisbenzyloxyphenyl]-5-hydroxy-4H-benzopyr-4-one (420mg, 0.63mmol) was treated with 5mL of N, N-...

Embodiment I-02

[0021] Example I-02: tert-butyl-N-[2-[2-(2-[3-[2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxyl-4-oxo Synthesis of -4H-benzopyran-6]propoxy]ethoxy)ethyl]carbamate

[0022]

[0023] Dissolve 2-(3,4-dihydroxy)3,5,7-trihydroxy-4H-chromen-4-one (1.0g, 3.31mmol) in 100mL of N,N-dimethylformamide In a 250mL round bottom flask, potassium carbonate (1.82g, 13.17mmol) was added simultaneously. Stir overnight at room temperature, and the reaction is complete. Add 200 mL of water to dilute the system, then extract with ethyl acetate (100 mL×2), combine the organic phases, and concentrate in vacuo. The residue was separated and purified by column chromatography, the developer was ethyl acetate / petroleum ether=1:20~1:10, and 1.2g of yellow solid 3,7-di(benzyloxy)-2-[3,4-di (Benzyloxy)phenyl]-5-hydroxy-4H-benzopyran-4-one, 55% yield.

[0024]3,7-bis(benzyloxy)-2-[3,4-bis(benzyloxy)phenyl]-5-hydroxyl-4H-benzopyran-4-one (7.0g, 10.56mmol) Dissolve in a 1000mL three-necked flask with a mixed ...

Embodiment I-03

[0028] Example I-03: Synthesis of 8-bromo-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-4H-benzopyran-4-one

[0029]

[0030] Dissolve 2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-4H-chromen-4-one (500 mg, 1.65 mmol) in 10 mL of dichloromethane in a 50 mL round bottom In the flask, acetic anhydride (760mg, 7.44mmol) and pyridine (262mg, 3.31mmol) were added. Stir at room temperature for 3h, the reaction is complete. The reaction solution was directly concentrated in vacuo, and the resulting crude product was crystallized from a mixed solution of ethanol / water=10:1 to obtain 0.5 g of light yellow solid 3-(acetoxy)-2-[3,4-bis(acetoxy) Phenyl]-5-hydroxy-4-oxo-4H-chromene-7-acetate, yield 64%.

[0031] 3-(Acetoxy)-2-[3,4-bis(acetoxy)phenyl]-5-hydroxy-4-oxo-4H-chromene-7-acetate (50mg, 0.11 mmol) was dissolved in 5mL carbon tetrachloride in a 50mL round bottom flask, and N-bromosuccinimide (19mg, 0.11mmol) and (3mg, 0.01mmol) succinimide were added. The whole reaction system was stir...

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Abstract

The invention discloses a 7,4',5'-trihydroxyflavanone derivative and its application in the preparation of liver cancer treatment medicines. The 7,4',5'-trihydroxyflavanone derivative can be used as the compound of antitumor medicines, and has a specific curative effect on cancers, especially the liver cancer. The structure of the derivative is represented by general formula (I) shown in the specification. In-vitro pharmacological experiments show that the 7,4',5'-trihydroxyflavanone derivative having the structural general formula I has an obvious antitumor activity and a good antitumor medicine exploitation and application prospect as an antitumor medicine.

Description

technical field [0001] The invention belongs to the technical field of medicine, and relates to a 7,4',5'-trihydroxyflavone derivative and its application in the preparation of drugs for treating liver cancer. Background technique [0002] Malignant tumors are a common disease that seriously threatens human health. The mortality rate caused by malignant tumors ranks second, second only to cardiovascular diseases. According to incomplete statistics, there are nearly 20 million new cases worldwide every year. The latest statistics show that there are about 2.2 million new cancer cases in China every year, and about 1.6 million cancer deaths, accounting for one-fifth of the disease deaths. At present, there are mainly drug therapy, surgical therapy and radiotherapy for the treatment of tumors. Drug therapy has become an important means of clinical tumor treatment today. Antineoplastic drugs mainly used in clinic can be roughly divided into drugs that destroy DNA structure an...

Claims

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Application Information

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IPC IPC(8): C07D311/30A61K31/352A61P35/00A61P1/16
Inventor 卢久富
Owner SHAANXI UNIV OF TECH
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