Chrysin derivative and preparation thereof and application thereof in treating hyperuricemia

A technology for hyperuricemia and chrysin, which is applied in the directions of drug combinations, medical preparations containing active ingredients, organic active ingredients, etc., can solve problems such as no reports of chrysin derivatives, and achieve convenient clinical medication and good response. Yield, good operability effect

Active Publication Date: 2016-08-24
JILIN ACAD OF TRADITIONAL CHINESE MEDICINE +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The research on the application of chrysin derivatives in anti-hyperuricemia drugs by selectively introducing active functional groups containing fluorine atoms has not been reported, and the prepared chrysin derivatives have not been reported after literature search. important application value

Method used

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  • Chrysin derivative and preparation thereof and application thereof in treating hyperuricemia
  • Chrysin derivative and preparation thereof and application thereof in treating hyperuricemia
  • Chrysin derivative and preparation thereof and application thereof in treating hyperuricemia

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] The preparation of embodiment 1 compound I-1

[0024] Take 0.254g of chrysin (1mmol) in a reaction flask, add dimethylformamide DMF to dissolve it, 10ml, then add 480ul (5.9mmol) of 37% formaldehyde solution, stir vigorously at 65°C for 30min, then add 160ul of benzylamine (1.5mmol), the reaction solution was stirred at this temperature for 3h and the reaction was completed. The reaction solution was evaporated to dryness under reduced pressure, the residue was dissolved in water, and 5% sodium hydroxide solution was added to adjust the pH value to 9, extracted with ethyl acetate, and combined Ethyl acetate solution was dehydrated with anhydrous MgSO4, filtered, evaporated to dryness under reduced pressure, and subjected to silica gel column chromatography to obtain compound Ⅰ-1.

[0025] Compound Ⅰ-1 5,7-dihydroxy-2-phenyl-8-((benzylamino)methyl)-4-H-benzopyran-4-one

[0026] Light yellow crystals, yield: 58.81%; 1 H-NMR (CDCl 3 ,300MHz)3.95(s,2H,Ar-CH 2 -NH),4.21(...

Embodiment 2

[0028] The preparation of embodiment 2 compound Ⅰ-2

[0029] Take 0.254g chrysin (1mmol) in a reaction flask, add dimethylformamide DMF to dissolve it, 10ml, then add 480ul (5.9mmol) of 37% formaldehyde solution, stir vigorously at 65°C for 30min, then add 2-fluoro Aniline 166ul (1.5mmol), the reaction solution was stirred at this temperature for 2.5h after the reaction was completed, the reaction solution was evaporated to dryness under reduced pressure, the residue was dissolved in water, and 5% sodium hydroxide solution was added to adjust the pH value to 9, ethyl acetate Extract, combine ethyl acetate solution, dehydrate with anhydrous MgSO4, filter, evaporate to dryness under reduced pressure, and go through silica gel column chromatography to obtain compound Ⅰ-2.

[0030] Compound Ⅰ-2 8-((2-fluoroanilino)methyl)-5,7-dihydroxy-2-phenyl-4H-1-benzopyran-4-one

[0031] Light yellow crystals, yield: 47.22%; 1 H-NMR (CDCl 3 ,300MHz)δ:4.59(s,2H,Ar-CH 2 -NH),6.47(s,1H,=C(OH)...

Embodiment 3

[0033] The preparation of embodiment 3 compound Ⅰ-3

[0034]Take 0.254g chrysin (1mmol) in a reaction flask, add dimethylformamide DMF to dissolve it, 10ml, then add 480ul (5.9mmol) of 37% formaldehyde solution, stir vigorously at 65°C for 30min, then add 3-fluoro Aniline 166 (1.5 mmol), the reaction solution was stirred at this temperature for 1.5 h and the reaction was complete. The reaction solution was evaporated to dryness under reduced pressure, the residue was dissolved in water, the pH value was adjusted to 9 by adding 5% sodium hydroxide solution, extracted with ethyl acetate, the ethyl acetate solution was combined, dehydrated with anhydrous MgSO4, filtered, evaporated to dryness under reduced pressure, and purified by silica gel Column chromatography yielded compound Ⅰ-3.

[0035] Compound Ⅰ-3 8-((3-fluoroanilino)methyl)-5,7-dihydroxy-2-phenyl-4H-1-benzopyran-4-one

[0036] Light yellow crystals, yield: 49.78%; 1 H-NMR (CDCl 3 ,300MHz)δ:4.64(s,2H,Ar-CH 2 -NH),6...

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PUM

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Abstract

The invention relates to a chrysin derivative and preparation thereof and application thereof in treating hyperuricemia, and belongs to the field of pharmaceutical synthesis. By using easily-obtained natural product chrysin as a starting material and selectively introducing active functional groups containing fluorine atoms, chrysin derivatives (I) and (II) are synthesized; a synthetic method is simple and is well operable and high in reaction yield, the obtained chrysin derivatives has significantly enhanced anti-hyperuricemia activity when compared to lead compound chrysin and is useful in treating hyperuricemia.

Description

technical field [0001] The invention belongs to the field of drug synthesis, and relates to chrysin derivatives and a preparation method thereof, in particular to a novel class of chrysin derivatives and a preparation method thereof, and the application of such compounds in the preparation of antihyperuricemia drugs . Background technique [0002] Uric acid is the final product of human purine and nucleic acid catabolism. The sources of uric acid include endogenous uric acid and exogenous uric acid. Endogenous uric acid is mainly synthesized by glutamic acid in the liver, but there is also internal protein decomposition in the body; exogenous uric acid Mainly eat foods rich in purines. In recent years, with the improvement of people's living standards, a large number of epidemiological studies at home and abroad have shown that the prevalence of hyperuricemia / gout is increasing year by year. [0003] Xanthine oxidase is the key enzyme in the uric acid production reaction i...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D311/30C07D498/04A61K31/5365A61K31/352A61P19/06
CPCC07D311/30C07D498/04
Inventor 仲崇琳杨美林全哲山林红
Owner JILIN ACAD OF TRADITIONAL CHINESE MEDICINE
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