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Flavone analog, preparation and application thereof as anti-diabetic medicament

A technology of analogs and flavonoids, applied in the field of medicinal chemistry, can solve the problems of low efficacy, large dose, and little clinical significance.

Inactive Publication Date: 2011-04-06
TIANJIN MEDICAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The doses of these compounds are large and the efficacy is low, and some lack the comparison of positive control drugs, so the clinical significance is not great

Method used

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  • Flavone analog, preparation and application thereof as anti-diabetic medicament
  • Flavone analog, preparation and application thereof as anti-diabetic medicament
  • Flavone analog, preparation and application thereof as anti-diabetic medicament

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] Synthetic General Method of Compound I-Xa

[0033]Synthesis of 2-Hydroxy-4,6-bis(methoxymethoxy)acetophenone

[0034] Weigh an appropriate amount of 2,4,6-trihydroxyacetophenone and dissolve it with an appropriate amount of anhydrous acetone, add 7 equivalents of potassium carbonate and stir, add 2.2 equivalents of chloromethyl methyl ether (MOMCl) dropwise with a dropping funnel, heat to reflux, and TLC Monitor until the reaction is complete. The reaction solution was cooled to room temperature and filtered, and the filtrate was concentrated under reduced pressure to obtain a crude product, which was subjected to flash silica gel column chromatography to obtain pure product 2-hydroxy-4,6-bis(methoxymethoxy)acetophenone.

[0035] Synthesis of Substituted Chalcone Derivatives I-Xa

[0036] Weigh an appropriate amount of 2-hydroxy-4,6-bis(methoxymethoxy)acetophenone into a reaction flask, and add an appropriate amount of methanol to dissolve it. Add 30 equivalents of 6...

Embodiment 2

[0039] Synthetic General Method of Series Compounds I-X

[0040] Synthesis of Compounds I-Xb

[0041] Weigh an appropriate amount of the corresponding chalcone compound I-Xa and dissolve it in an appropriate amount of ethanol, add 4.5 equivalents of sodium acetate, dropwise add 1-3 drops of distilled water, heat to reflux, and monitor by TLC until the product point intensity does not change. The reaction solution was cooled to room temperature and poured into an appropriate amount of water, extracted three times with ethyl acetate, combined organic phases, dried over anhydrous magnesium sulfate, filtered, and concentrated to obtain a crude product, which was subjected to flash silica gel column chromatography to obtain pure product I-Xb.

[0042] Synthesis of Compounds I-X

[0043] Weigh an appropriate amount of hydroxyl-protected dihydroflavone compounds I-Xb, dissolve them in an appropriate amount of methanol, add 1.5 equivalents of 3mol / l hydrochloric acid, stir and heat t...

Embodiment 3

[0058] Synthesis of 2-(3-chloro-4-hydroxyphenyl)-5,7-dihydroxybenzopyran-4-one (II-1)

[0059] Weigh an appropriate amount of the corresponding chalcone compound I-Xa, dissolve it with an appropriate amount of anhydrous pyridine, add 0.1 equivalent of solid iodine, stir and heat to reflux, and monitor by TLC until the reaction is complete. After the reaction solution was cooled to room temperature, an appropriate amount of ethyl acetate was added, washed three times with saturated sodium chloride solution, the organic phase was dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure to obtain crude product II-Xa.

[0060] Weigh an appropriate amount of the crude product II-Xa obtained in the previous step, dissolve it in an appropriate amount of methanol, add 15 equivalents of 3 mol / l hydrochloric acid, stir and heat to reflux, and monitor by TLC until the reaction is complete. The reaction solution was poured into ice water, extracted three t...

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PUM

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Abstract

The invention discloses a flavone analog and application of a pharmaceutically acceptable salt thereof to preparation of an anti-diabetic medicament. The flavone analog has a structure shown by a formula I-X or II-X, wherein R1 in the formula I-X or II-X is selected from a substituted phenyl group, a substituted or unsubstituted furan group and a substituted or unsubstituted thienyl group and the substituent group is selected from a C1-4 alkyl group, a C1-4 alkoxyl group, halogen, a hydroxyl group and a cyano group; R2 is selected from the substituted phenyl group, the substituted or unsubstituted furan group and the substituted or unsubstituted thienyl group and the substituent group is selected from the halogen, the hydroxyl group and the cyano group.

Description

technical field [0001] The invention synthesizes a series of flavonoids and dihydroflavone analogues, the compounds can be used as medicines for treating diabetes and belong to the field of medicinal chemistry. Background technique [0002] Diabetes mellitus is a common endocrine and metabolic disease characterized by high blood sugar and multiple complications caused by absolute or relative insulin deficiency. It can be divided into type 1 and type 2 diabetes. It is a common chronic disease that seriously endangers human health. lifelong disease. Diabetes is not an incurable disease, but so far, no country can cure it. Since the 1990s, with the development of society and the trend of population aging, diabetes has become a worldwide disease. In industrialized countries, it is second only to cancer and cardiovascular and cerebrovascular diseases. Diabetes has become the concern of all countries in the world. major public health problem. In our country, its incidence rate ...

Claims

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Application Information

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IPC IPC(8): A61K31/352A61K31/381A61P3/10C07D311/32C07D311/30C07D409/04C07D407/04
Inventor 段宏泉常留栓张艳军秦楠靳美娜周雯
Owner TIANJIN MEDICAL UNIV
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