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Method for preparing scutellarin

A technology of acetylation and compounds, applied in the field of drug synthesis, can solve the problems of low yield, lack of raw material sources, cumbersome process, etc., and achieve the effect of high yield, rich source, and simple process

Active Publication Date: 2011-01-12
KPC PHARM INC +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In order to solve the defects of the chemical synthesis method of scutellarin in the prior art, such as lack of raw

Method used

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  • Method for preparing scutellarin
  • Method for preparing scutellarin
  • Method for preparing scutellarin

Examples

Experimental program
Comparison scheme
Effect test

Example Embodiment

Example 1:

Step 1: Preparation of compound II

Weigh 18.4g (0.1mol) 3,4,5-trimethoxyphenol into the reaction vessel, add about 30ml acetic anhydride, and slowly add BF while stirring at room temperature 3 The solution was 10ml, and then slowly heated to 40°C to react for 3 hours (TLC checked that the raw material had reacted completely).

The above reaction solution was naturally cooled slightly, 100 ml of ethyl acetate was added and stirred, and then placed in the refrigerator overnight, and filtered to obtain a yellow solid precipitated. Add 100 ml of water and 10 ml of ethanolamine to the yellow solid, stir thoroughly for 1 to 2 hours, and then extract the product with ethyl acetate twice, each with 80 ml. The extracts were combined, washed once with water, dried over anhydrous sodium sulfate, filtered, and evaporated to remove the solvent under reduced pressure to obtain compound II as a light yellow oil, which can be solidified after being refrigerated and dried and weighed...

Example Embodiment

Example 2:

Step 1: Preparation of compound II

Weigh 18.4g (0.1mol) 3,4,5-trimethoxyphenol into the reaction vessel, add about 30ml acetic acid, slowly add 50g polyphosphoric acid under stirring at room temperature, and then slowly heat to 80°C for 1 hour (TLC Check that the raw materials have reacted completely).

Under stirring, the above reaction solution was poured into 150 ml of ice-cold water while it was hot, and then the product was extracted twice with 100 ml of ethyl acetate. The extracts were combined, washed once with water, dried over anhydrous sodium sulfate, filtered, and evaporated to remove the solvent under reduced pressure to obtain compound II as a light yellow oil, which can be solidified after being refrigerated and dried and weighed. The yield: 85%. 1 HNMR(CDCl 3 ):Cit.

Step 2: Preparation of compound III

Weigh 15.2g (0.10mol) 3,4,5-trimethoxybenzoic acid into the reaction flask, add 40ml dichloromethane, 15ml SOCl 2 (Thionyl chloride) and 2~5 drops of D...

Example Embodiment

Example 3:

Step 1: Preparation of compound II

Weigh 4.0 g (0.011 mol) of Compound IV into the reaction flask, and add 50 ml of hydroiodic acid acetic acid solution. After mixing, heat to 100°C and react for 15 hours under nitrogen protection (TLC checks that the raw materials have reacted completely).

Under stirring, the above reaction solution was poured into 150 ml of ice-cold water while it was hot, and then the product was extracted twice with 100 ml of ethyl acetate. The extracts were combined, washed once with water, dried over anhydrous sodium sulfate, filtered, and evaporated to remove the solvent under reduced pressure to obtain compound II as a light yellow oil, which can be solidified after being refrigerated and dried and weighed. The yield: 85%. 1 HNMR(CDCl 3 ):Cit.

Step 2: Preparation of compound III

Weigh 15.2g (0.10mol) 3,4,5-trimethoxybenzoic acid into the reaction flask, add 40ml dichloromethane, 15ml SOCl 2 (Thionyl chloride) and 2~5 drops of DMF (N,N~dime...

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PUM

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Abstract

The invention relates to a method for preparing compound scutellarin with a structural formula as the formula I. The method is to prepare high-purity scutellarin by using 3,4,5-trimethoxyphenol as an initial raw material through acylation to form ester and phenol ester rearrangement, benzoylation to form ester and Baker-Venkarama rearrangement, cyclization, methoxyl removal and acetylization, alkylation, hydrogenolysis debenzylation, alkylation to form glucoside, neutralization with acid after basic hydrolysis in the absence of oxygen. The method for preparing the scutellarin has the yield reaching over 20 percent, has rich raw material sources, simple process and low cost, and has wide industrial application prospect.

Description

Technical field The invention relates to the field of drug synthesis, in particular to a method for preparing scutellarin. Background technique: Breviscapine, also known as scutellarin, its systematic name is 4',5,6-trihydroxyflavone-7β-O-glucuronide, which is the main pharmacology of the Yunnan national medicine breviscapine and its extract preparations The structural formula of the active ingredient is shown in Formula I. Scutellarin can achieve its obvious protective effect on acute cerebral ischemia through a variety of mechanisms of action: it can inhibit platelet aggregation, inhibit blood coagulation in the body and promote fibrinolytic activity, thereby inhibiting thrombosis; it is caused by inhibiting protein kinase C activation Cerebral vasospasm contraction, increase local cerebral blood flow, improve cerebral microcirculation, reduce inflammatory cell adhesion and infiltration, and protect brain tissue after ischemia; it can also accelerate cerebral blood flow, in...

Claims

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Application Information

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IPC IPC(8): C07H17/07C07H1/00A61P7/02A61P9/10A61P9/00
Inventor 杨健杨兆祥杨波普俊学张伟陈铎之
Owner KPC PHARM INC
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