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Apigenin derivatives and their application in the treatment of hyperuricemia

A technology of hyperuricemia and apigenin, applied in drug combination, bone diseases, organic chemistry, etc., can solve problems such as many side effects, and achieve the effects of improved bioavailability, increased water solubility, and good oil-water partition coefficient

Active Publication Date: 2018-07-24
JILIN ACAD OF TRADITIONAL CHINESE MEDICINE +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, allopurinol and febuxostat, a non-purine xanthine oxidase inhibitor, are the main anti-hyperuric acid drugs, but both have many side effects

Method used

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  • Apigenin derivatives and their application in the treatment of hyperuricemia
  • Apigenin derivatives and their application in the treatment of hyperuricemia
  • Apigenin derivatives and their application in the treatment of hyperuricemia

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] The preparation of embodiment 1 compound I-1

[0026] Take 2.70g apigenin (10mmol) in the reaction flask, add 50ml of dimethylformamide to dissolve it, add 1.50ml (15mmol) of N-methylpiperazine, then add 1.23ml (15mmol) of 37% aqueous formaldehyde, and mix Evenly, react for 60 minutes at a temperature of 45°C in a microwave synthesizer with a set power of 350 watts to obtain a reaction solution; cool the reaction solution to room temperature, add 50ml of water and 100ml of ethyl acetate for extraction, ethyl acetate solution, no Dehydrated with sodium sulfate, the ethyl acetate solution was evaporated to dryness under reduced pressure, the residue was dissolved in acetone and allowed to stand at room temperature, and the precipitate was recrystallized with acetone to obtain compound I-1.

[0027] Compound I-1 8-(4-methylpiperazine-1-methyl)-5,7-dihydroxy-2-(4-phenol)-4H-1-benzopyran-4-one, light yellow Crystallization, yield: 68.81%; 1 H-NMR (CD 3 OD,300MHz):δ2.53(q,...

Embodiment 2

[0030] The preparation of embodiment 2 compound 1-2

[0031] Get 2.70g apigenin (10mmol) in the reaction flask, add dimethylformamide 50ml to make it dissolve, add N ethylpiperazine 1.71ml (15mmol), then add 37% formaldehyde aqueous solution, 1.23ml (15mmol), mix Evenly, react for 60 minutes at a temperature of 45°C in a microwave synthesizer with a set power of 350 watts to obtain a reaction solution; cool the reaction solution to room temperature, add 50ml of water and 100ml of ethyl acetate for extraction, ethyl acetate solution, no Dehydrated with sodium sulfate, the ethyl acetate solution was evaporated to dryness under reduced pressure, the residue was dissolved in acetone, left at room temperature, and the precipitate was recrystallized with acetone to obtain compound I-2.

[0032] Compound I-2 8-(4-ethylpiperazine-1-methyl)-5,7-dihydroxy-2-(4-phenol)-4H-1-benzopyran-4-one, light yellow Crystallization, yield: 67.22%; 1 H-NMR (CD 3 OD,300MHz):δ2.20(s,3H,-CH 3 ),2.36...

Embodiment 3

[0035] The preparation of embodiment 3 compound 1-3

[0036]Take 2.70g apigenin (10mmol) in the reaction flask, add 50ml of dimethylformamide to dissolve it, add 1.92ml (15mmol) of 1-isopropylpiperazine, then add 1.23ml (15mmol) of 37% formaldehyde solution , mixed evenly, and reacted for 60 minutes at a temperature of 45°C in a microwave synthesizer with a set power of 350 watts to obtain a reaction solution; the reaction solution was cooled to room temperature, extracted with 50ml of water and 100ml of ethyl acetate, and the ethyl acetate solution , dehydrated with anhydrous sodium sulfate, the ethyl acetate solution was evaporated to dryness under reduced pressure, the residue was dissolved in acetone, left at room temperature, and the precipitate was recrystallized with acetone to obtain compound I-3.

[0037] Compound I-3 8-(4-isopropylpiperazine-1-methyl)-5,7-dihydroxy-2-(4-phenol)-4H-1-benzopyran-4-one, shallow Yellow crystal, yield: 69.78%; 1 H-NMR (CD 3 OD,300MHz):...

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Abstract

The present invention relates to apigenin derivatives and an application of the apigenin derivatives in treatment of hyperuricemia, and belongs to the field of medicinal chemistry. The invention discloses the apigenin derivatives shown in a formula (I), and the invention also discloses the application of the apigenin derivatives in preparation of anti-hyperuricemia medicines. According to the invention, the novel apigenin derivatives are synthesized by taking natural product apigenin which is easy to obtain as a starting raw material, and the synthetic method is simple, and has the better operability and reaction yield; and the prepared apigenin derivatives have obvious anti-hyperuricemic activity, and are used for treating the hyperuricemia and gout diseases.

Description

technical field [0001] The invention relates to the field of medicinal chemistry, in particular to apigenin derivatives and their application in treating hyperuricemia. Background technique [0002] Flavonoids can prevent and treat hyperuricemia and gout through multiple mechanisms and multiple targets, but the results of a large number of animal experiments show that their oral bioavailability is often less than 10%, making their pharmacological activity low. Apigenin is a kind of flavonoids, which are mostly found in fruits, vegetables, beans and tea, among which celery has the highest content. The molecular structure of apigenin determines its unique physiological effects and biological characteristics. It has good biological effects and is a natural antioxidant. It has the effects of lowering blood pressure, relaxing blood vessels, preventing atherosclerosis, and inhibiting tumors. At present, apigenin has certain applications in medicine, food and other industries. Du...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D311/30A61P19/06
CPCC07D311/30
Inventor 仲崇琳杨美林徐军佟慧
Owner JILIN ACAD OF TRADITIONAL CHINESE MEDICINE
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