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Method for preparing scutellarin

A technology of scutellarin and dichloroethane, which is applied in the preparation of sugar derivatives, chemical instruments and methods, sugar derivatives, etc., can solve the problems of difficult industrial application, cumbersome process operation, high price, etc., and achieve high-efficiency chemical synthesis. The effect of preparation, operation safety, easy production control

Active Publication Date: 2016-01-06
KUNMING UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, because its synthetic starting material 2-hydroxyl-4,5,6-trimethoxyacetophenone is currently not supplied in large quantities on the market, only a small amount is imported and the price is expensive, and its original report process operation is too complicated, and the reagents used are tested. The special medicine and high price make it not easy to realize industrial application

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0041] Example 1: The preparation method of this scutellarin is as follows:

[0042] (1) Synthesis of Compound 3: Weigh 23.5g (0.25mol) of phenol into a 1000ml round bottom flask, add 300ml of methanol and 130ml of commercially available hydrobromic acid with a concentration of 47% by mass, and then slowly Add 90ml of hydrogen peroxide with a mass percent concentration of 30% dropwise therein, and control the dropping rate so that the temperature of the reaction solution does not exceed 40°C, and the addition is completed in about 1 to 2 hours. After addition, continue to stir for 1-2 hours, add a little sodium bisulfite, filter after a few minutes, wash the filter cake with a small amount of methanol, press dry, and dry at 70-80°C to obtain a white powdery solid, namely compound 3; Weighing: 82.0g, yield: 98%. 1 HNMR (DMSO): δ9.92(s, 1H), δ7.46(s, 2H).

[0043] (2) Synthesis of Compound 4: Weigh 84.0g (1.5mol) of sodium methoxide into a 1000ml round bottom flask, add 200m...

Embodiment 2

[0058] Example 2: The preparation method of this scutellarin is as follows:

[0059] (1) Synthesis of Compound 3: Weigh 23.5g (0.25mol) of phenol into a 1000ml round bottom flask, add 500ml of ethanol, 80g (0.78mol) of sodium bromide and 20ml (0.40mol) of commercially available 98% concentrated sulfuric acid , then slowly add 90ml of hydrogen peroxide with a mass percentage concentration of 30% to it under vigorous stirring at room temperature, control the rate of addition so that the temperature of the reaction solution does not exceed 45°C, and add it in about 1-2 hours; after the addition, continue to stir for 1- After 2 hours, add a little sodium bisulfite, filter after a few minutes, wash the filter cake with a small amount of distilled water, press dry, and dry at 70-80°C to obtain a white powdery solid, that is, compound 3. Weighing: 82.0g, yield: 99%. 1 HNMR (DMSO): same as step (1) of Example 1 above.

[0060] (2) Synthesis of compound 4: Weigh 84.0g (1.5mol) of s...

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PUM

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Abstract

The invention discloses a method for preparing scutellarin. The method comprises the following steps: taking phenol as a starting material, preparing a chalcone intermediate compound 6 through bromination, methoxy substitution, friedel-crafts acylation and the like, performing oxidative cyclisation on the chalcone intermediate compound 6 to obtain a key flavone intermediate 4',6-dihydroxy-5,7-dimethoxy flavone-compound 7, and preparing high-purity scutellarin through benzoylation, selective demethylation, glycosylation and hydrolysis reaction of the key intermediate. According to the method, the adopted raw material reagents are all low in price and easy to obtain, the synthesis steps are less, the operation is simple and convenient, production control is easy, the product yield and purity are high, and the method is suitable for scutellarin production.

Description

technical field [0001] The invention relates to a method for preparing scutellarin, a drug for treating diseases such as cardiovascular and cerebrovascular diseases. Background technique [0002] Scutellarin, also known as scutellarin, scutellarin, etc., that is, 4',5,6-trihydroxyflavone-7-O-β-glucuronide, is a Yunnan national medicine scutellaria breviscapus and its extract preparation The main pharmacological active ingredients in the drug have pharmacological effects such as dilating blood vessels, reducing blood viscosity, reducing peripheral resistance, reducing platelet count, inhibiting platelet aggregation, increasing blood supply to the heart and brain, and its preparations are mainly used clinically for coronary heart disease, angina pectoris, myocardial The treatment of cardiovascular and cerebrovascular diseases such as ischemia, cerebral thrombosis and their sequelae has shown definite and excellent curative effect. Studies in recent years have shown that it ca...

Claims

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Application Information

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IPC IPC(8): C07H17/07C07H1/00
Inventor 杨健王谦崔巍杨波廖霞俐
Owner KUNMING UNIV OF SCI & TECH
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