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Flavone derivatives and their preparative method and medical use

一种衍生物、黄酮的技术，应用在新黄酮衍生化合物领域，能够解决临床意义不大、作用剂量大、缺乏阳性对照药等问题

Inactive Publication Date: 2014-08-20
TIANJIN MEDICAL UNIV +6
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The dosage of these compounds is large and the efficacy is low, the clinical significance is not great, and some of them lack the comparison of positive control drugs.

Method used

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  • Flavone derivatives and their preparative method and medical use
  • Flavone derivatives and their preparative method and medical use
  • Flavone derivatives and their preparative method and medical use

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037] Synthetic General Method of Series Compound II

[0038]Weigh an appropriate amount of substituted benzaldehyde into a reaction flask, add excess acetone, and stir at room temperature to fully dissolve the raw materials. Add 1.5 equivalents of 4 mol / L sodium hydroxide solution to the reaction flask at room temperature, and stir the reaction solution at 40°C. TLC monitored until the reaction was complete. The reaction solution was concentrated under reduced pressure to remove excess acetone. Add 1 mol / L dilute hydrochloric acid to the residue to adjust the pH to be slightly acidic. Extract with appropriate amount of dichloromethane 3 times, and combine the organic phases. The organic phase was dried with anhydrous magnesium sulfate, filtered, and concentrated to obtain a crude product, which was subjected to flash silica gel column chromatography to obtain a series of compounds II shown in Formula 4.

[0039]

[0040] Formula 4

Embodiment 2

[0042] Synthetic general method of series compound III:

[0043] Weigh an appropriate amount of compound II into a reaction flask, and add tetrahydrofuran to dissolve it. 1.2 equivalents of pyrrolidone hydrotribromide (PHT) was weighed and dissolved in an appropriate amount of tetrahydrofuran, and the solution was slowly dropped into the reaction flask at room temperature. After the dropping, it was stirred at room temperature for 24 h, or monitored by TLC until the reaction was complete. After the reaction was completed, the white insoluble matter was removed by filtration, and the filtrate was collected. The tetrahydrofuran in the filtrate was removed under reduced pressure, and the concentrate was subjected to flash silica gel column chromatography to obtain a series of compounds III shown in Formula 5.

[0044]

[0045]

[0046] Formula 5

Embodiment 3

[0048] Synthetic general method of series compound I:

[0049] Weigh kaempferol (1.2 equivalents), anhydrous K 2 CO 3 (1.2 equivalents) in the three-necked bottle, add dioxane 5ml to fully dissolve kaempferol, after the reaction solution was stirred for 1.5h under reflux, compound III (1 equivalent) was dissolved in 2ml dioxanes, and the The solution was added dropwise to the reaction solution under reflux, and the drop was completed in about half an hour. The reaction solution continued to reflux. After the disappearance of compound III was monitored by TLC, the reaction solution was cooled to room temperature, dioxane was removed under reduced pressure, dilute hydrochloric acid was added to the residue to adjust the pH value to acidity, extracted with ethyl acetate, and the organic phase was dried with anhydrous magnesium sulfate , filtered and concentrated. The crude product was separated by HW-40c gel column chromatography, dichloromethane-methanol (1:1, V / V) was used ...

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PUM

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Abstract

Flavone derivatives, preparative method of the derivatives and use thereof as medicaments for treating diabetes. The structure of the derivatives is presented by formula 1: In the structure, R1 and R2, which are identical or not, represent hydrogen atom, halogen, cyano, hydroxyl, trifluoromethyl, thio-methyl, benzyloxy, C1-C8 linear chain or branch chain alkyl, C1-C8 linear chain or branch chain alkoxy. The pharmacological test indicates that the flavone derivatives can significantly increase the glucose consumption of Hep-G2 cell with insulin resistance activity, promote translocation of glucose transporter 4 of skeletal muscle cells (L6GLUT4myc) at different level, and significantly increase glucose intake and utilization by cells. The test proves the fact for the first time that the flavone derivatives can significantly promote translocation of glucose transporter 4 of skeletal muscle cells, and one of the mechanisms for treating diabetes is activating the cell AMPK phosphorylation and phosphorylating the downstream ACC.

Description

technical field [0001] The invention relates to a class of new flavonoid derivative compounds, a preparation method and application as antidiabetic drugs. belongs 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 my country, its incidence has risen from 0...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D311/30A61K31/352A61P3/10
CPCC07D311/30A61K31/35A61P3/10A61P43/00
Inventor 段宏泉秦楠牛文彦靳美娜史利欢陈莹
Owner TIANJIN MEDICAL UNIV
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