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5,6,7,4'-4 acetoxy flavone and preparation method thereof

A tetraacetoxyflavone, acetylation technology, applied in the field of medicine, can solve the problems of poor stability, easy oxidation and deterioration of phenolic hydroxyl groups, etc.

Inactive Publication Date: 2011-08-10
KPC PHARM INC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The present invention aims at the disadvantages of existing 5,6,7,4'-tetrahydroxyflavone that the phenolic hydroxyl group is easily oxidized and deteriorated, and has poor stability, and provides a structurally stable 5,6,7,4'-tetrahydroxyflavone derivative, Its structural formula is as follows:

Method used

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  • 5,6,7,4'-4 acetoxy flavone and preparation method thereof
  • 5,6,7,4'-4 acetoxy flavone and preparation method thereof
  • 5,6,7,4'-4 acetoxy flavone and preparation method thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0027] Example 1: Synthesis of 5,6,7,4'-tetraacetoxyflavone

[0028] Put 10.0 g of 5,6,7,4'-tetrahydroxyflavone and 75 ml of acetic anhydride in a 300 ml Erlenmeyer flask, add 1 drop (about 0.1 ml) of concentrated hydrochloric acid or perchloric acid, and stir magnetically at room temperature for 1 hour. TLC detects that the raw material point disappears, filters and washes until neutral, and dries the filtrate to obtain 5,6,7,4'-tetraacetoxyflavone. The yield is 92%, and the purity is 98.2% as detected by HPLC.

Embodiment 2

[0029] Example 2: Synthesis of 5,6,7,4'-tetraacetoxyflavone

[0030] Put 10.0g of 5,6,7,4'-tetrahydroxyflavone and 75ml of acetic anhydride in a 300ml Erlenmeyer flask, add 10 drops of oxalic acid or triethylamine (about 1ml) dropwise, stir magnetically at room temperature for 1 hour, and detect by TLC The raw material point disappears, filter and wash with water until neutral, and dry the filtrate to obtain 5,6,7,4'-tetraacetoxyflavone. The yield is 91%, and the purity is 98.1% as detected by HPLC.

Embodiment 3

[0031] Example 3: Synthesis of 5,6,7,4'-tetraacetoxyflavone

[0032] Put 10.0 g of 5,6,7,4'-tetrahydroxyflavone and 75 ml of acetic anhydride in a 300 ml Erlenmeyer flask, add sodium hydroxide or sodium bicarbonate aqueous solution (about 10 ml) dropwise, stir magnetically at room temperature for 1 hour, and test by TLC Detect the disappearance of raw material points, filter and wash with water until neutral, and dry the filtrate to obtain 5,6,7,4'-tetraacetoxyflavone. The yield is 92%, and the purity is 98.5% as detected by HPLC.

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Abstract

The invention relates to the field of medicine and discloses a novel compound 5,6,7,4'-4 acetoxy flavone. The compound is greatly stable in acid, water and air, cannot be oxidized or deteriorated, has low toxicity and high lipid solubility and is beneficial for being adsorbed by a human body. The invention also provides a method for preparing the compound. In the method, blue 5,6,7,4'-tetrahydroxy flavone is used as the raw material; and 5,6,7,4'-4 acetoxy flavone is obtained by introducing acetyl groups onto four hydroxy positions of a parent nucleus. The method has mild reaction conditions,high yield and simple process and is suitable for industrial production.

Description

technical field [0001] The invention relates to the field of medicine, in particular to 5,6,7,4'-tetraacetoxyflavone and a preparation method thereof. Background technique [0002] In recent years, with the rapid development of economy, the improvement of people's living standards, the aging of the population, and the increasing number of cardiovascular and cerebrovascular diseases, the incidence and mortality of cardiovascular and cerebrovascular diseases in China have shown a linear upward trend, causing huge health threats and economic burdens. Therefore, Its pathogenesis and treatment have received special attention from the medical community. [0003] Flavonoid derivatives mostly have the effect of treating and preventing cardiovascular and cerebrovascular diseases. At present, scutellarin has been widely used in the treatment of cardiovascular and cerebrovascular diseases. Clinical application shows that it can increase the blood flow of brain and coronary vessels, re...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D311/30
Inventor 周荣光
Owner KPC PHARM INC
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