Method for preparing scutellarin

An aglycone and breviscapine technology, which is applied in the direction of organic chemistry and the like, can solve the problems of difficult industrial application, difficult to obtain in large quantities, cumbersome process operation, etc., and achieves high industrial application value and economic value, simple and convenient operation, and good purity. Effect

Inactive Publication Date: 2016-08-31
KUNMING UNIV OF SCI & TECH
View PDF4 Cites 3 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, because its synthetic starting material 2-hydroxyl-4,5,6-trimethoxyacetophenone is currently not supplied in large quantities in the market, only a small amount is imported and the price is expensive. Reagents are special and expensive, making it difficult to realize industrial application
In 2011, Giuliana Righi et al. used the natural product naringenin as the starting material to synthesize scutellarin aglycon through 5 steps of reaction conversion, and obtained a good yield of 62% (see Giuliana Righi, et al. Efficientsynthesis of scutellarein, Natural Product Research: Formerly Natural Product Letters, 2012, 26(14), 1278-1284), but its starting material is the natural product naringenin, which is not easy to obtain in large quantities, and the price is relatively high, which also limits the The promotion and application of this method in industrial production

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Method for preparing scutellarin

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] (1) Synthesis of Compound 3: Weigh 16.8g (0.10mol) of 2,6-dimethoxy-p-benzoquinone (Compound 2) into a 250mL round-bottomed flask, add 10% sodium hydrosulfite aqueous solution 100mL (the molar amount of sodium hydrosulfite is 1 times the molar amount of compound 2), stirred at room temperature for about 3 hours, then filtered, washed the filter cake with a small amount of water, pressed dry, and dried under vacuum to obtain an off-white powdery solid, namely Compound 3; weighing: 17.0 g, yield: 100%. 1 HNMR (DMSO): δ5.73(s,2H), δ5.05(s,1H), δ3.77(s, 6H).

[0021] (2) Synthesis of Compound 4: Weigh 17.0g (0.10mol) of Compound 3 into a 250mL reaction bottle, add 100mL of chloroform and 25mL of acetic anhydride, then slowly add about 20mL of boron trifluoride ether solution under stirring at room temperature ( Boron trifluoride is 0.2mol); slowly heat the reaction mixture to about 90°C and react for about 10 hours; let it cool, add water dropwise, slowly heat up and evapo...

Embodiment 2

[0026] (1) Synthesis of Compound 3: Weigh 16.8g (0.10mol) of 2,6-dimethoxy-p-benzoquinone (Compound 2) into a 250mL round bottom flask, add 100mL industrial methanol and no less than 3.6g ( 0.15mol) of magnesium metal, heat the mixture to 60°C under stirring for about 5-6 hours, filter, wash with a little fresh methanol, combine the filtrate, evaporate methanol under reduced pressure to obtain an off-white powdery solid, the compound 3. Colorless crystals that can be recrystallized from a methanol-water mixed solvent, dried, weighed: 16.0 g, yield: 94.0%. 1 HNMR (DMSO): same as step (1) of Example 1;

[0027] (2) Synthesis of Compound 4: Weigh 17.0g (0.10mol) of Compound 3 into a 100mL reaction bottle, add 35mL of acetic acid, then slowly add about 10mL of phosphorus oxychloride under stirring at room temperature; slowly heat the reaction mixture to React at about 100°C for about 8 hours. Allow the reaction mixture to cool down and add dropwise to 200mL of water. The aqueous...

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to view more

PUM

No PUM Login to view more

Abstract

The invention relates to a method for preparing scutellarin. According to the method, the scutellarin can be efficiently prepared from 2,6-dimethoxy benzoquinone as a starting raw material through five reactions of reduction, Friedel-Crafts acetylation, Claisen condensation, dehydrogenation oxidation cyclization and demethylation. The starting raw material and a reagent are cheap and easily available, synthetic steps are few, the operation is simple and convenient, the production control is simple, the product yield is high, and the purity is high. The method is applicable to large-scale preparation and production application of the scutellarin.

Description

technical field [0001] The invention relates to a method for preparing scutellarin aglycon, a drug for treating cardiovascular and cerebrovascular diseases and the like. Background technique [0002] Scutellarin aglycone, the aglycon of scutellarin, chemical name: 4′,5,6,7-tetrahydroxyflavone. Scutellarin aglycon and scutellarin are the main pharmacological active ingredients in Yunnan national medicine scutellaria breviscapus and its extract preparations, which can dilate blood vessels, reduce blood viscosity, reduce peripheral resistance, reduce platelet count, inhibit platelet aggregation, increase It has pharmacological effects such as blood supply to the heart and brain, and its preparations are mainly used in the treatment of cardiovascular and cerebrovascular diseases such as coronary heart disease, angina pectoris, myocardial ischemia, cerebral thrombosis and its sequelae, and has shown definite and excellent curative effect. Studies in recent years have shown that ...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to view more

Application Information

Patent Timeline
no application Login to view more
Patent Type & Authority Applications(China)
IPC IPC(8): C07D311/30
CPCC07D311/30
Inventor 杨健王谦崔巍杨波
Owner KUNMING UNIV OF SCI & TECH
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Try Eureka
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap