Method for synthesizing 5,6,4'-trihydroxyflavone-7-O-D-glucuronic acid

A technology of glucuronic acid and trihydroxyflavone, applied in chemical instruments and methods, medical preparations containing active ingredients, sugar derivatives, etc., can solve the problems of long synthetic routes and low yields

Inactive Publication Date: 2009-09-23
四川抗菌素工业研究所有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Cui et al. (JIAN-Mei Cui, GANG Fang, YA-Bo Duan.Total synthesis of scutellarin-7-O-Glucuronide.Journal of Asian Natural Products Research.2005, 7(4):655-660) using the Baker-Venkataraman method The total synthesis of 5,6,4'-trihydroxyflavone-7-O-D-glucuronic acid has been completed by the propylene dione route, but there are shortcomings such as low yield and long synthetic route (see Figure II )

Method used

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  • Method for synthesizing 5,6,4'-trihydroxyflavone-7-O-D-glucuronic acid
  • Method for synthesizing 5,6,4'-trihydroxyflavone-7-O-D-glucuronic acid
  • Method for synthesizing 5,6,4'-trihydroxyflavone-7-O-D-glucuronic acid

Examples

Experimental program
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Effect test

Embodiment 1

[0016] Take 2.68g 3,4,5-triacetoxyphenol and 2.50g p-acetoxycinnamic acid chloride, put into 20mL BF 3 -Et 2 O solution, make it fully dissolved, add 2g 4A molecular sieve, heat under reflux for 15 minutes, stop heating, filter, recrystallize with petroleum ether-ethyl acetate (3:1) to obtain 9-hydroxy-5,6,7,4 '-Tetraacetoxychalcone, a total of 4.15g, the transfer rate of this step was 91%.

[0017] Take 4.56g of 9-hydroxy-5,6,7,4'-tetraacetoxychalcone, 200mg of iodine, dissolve in 25mL of DMSO, reflux for 2 hours, then carefully pour into 200g of crushed ice, filter, precipitate with 20% Na 2 SO 3 Washed and recrystallized with petroleum ether-ethyl acetate (10:1) to obtain 3.95 g of 5,6,7,4'-tetraacetoxyflavone with a transfer rate of 87%.

[0018] Take 4.54g 5,6,7,4'-tetraacetoxyflavone, 5.25g K 2 CO 3 , 0.21g KI, 2.3mL PhCH 2 Cl, placed in 600 mL of dry acetone, heated to reflux at 40-45 °C for 4 hours. After the reaction was completed, the solution was diluted wit...

Embodiment 2

[0023] Purification of target products

[0024]Take 100 g of the complete product, add 1000 mL of pure water, adjust the pH value to 7 with 30% sodium hydroxide solution to completely dissolve, filter, add 8 times acetone to the filtrate at 25 ° C for precipitation, add acetone while stirring , make the precipitation complete, stand for 12 hours, filter, add acetone to wash three times, then move the precipitate to another container, add 6 times the amount of 40% acetone, stir well, add 25% hydrochloric acid to adjust the pH value to 1 ~2, stand for 10 hours, filter with suction, wash with water until neutral, add ethanol to wash once, and dry to obtain refined products. HPLC analysis showed that the content of 5,6,4'-trihydroxyflavone-7-O-D-glucuronic acid in the obtained sample was 99.31%.

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Abstract

The invention provides a chemical method for preparing 5,6,4'-trihydroxyflavone-7-O-D-glucuronic acid to solve problems of unavailable raw materials, long synthetic route and low synthesis yield in the existing synthetic method. The method comprises a plurality of chemical reaction steps: first, taking 3,4,5-trimethoxy phenol and p-methoxy cinnamoyl chloride as the raw materials to construct a chalcone structure by a Friedel-Crafts acylation reaction, and cycloetherifying to obtain a flavone parent substance; then protecting and selectively deprotecting phenolic hydroxyl of the flavone parent substance, and glycosylating 7-phenolic hydroxyl; and finally removing a protective group to obtain the target compound. The obtained product has a beta-steric configuration. The method can be used for preparing high-purity and high-quality 5,6,4'-trihydroxyflavone-7-O-D-glucuronic acid products.

Description

Technical field: [0001] The invention relates to the field of medicinal chemistry, in particular to a method for synthesizing 5,6,4'-trihydroxyflavone-7-O-D-glucuronic acid. Background technique [0002] Among natural medicines, flavonoids are the most common type of flavonoids, accounting for more than a quarter of the total number of flavonoids, with obvious structural diversity. It has been found that flavonoids have a variety of physiological activities, mainly including: anti-cardiovascular and cerebrovascular diseases, anti-inflammatory, anti-liver virus, liver protection, antibacterial, anti-cancer, antioxidant and other effects. Among them, 5,6,4'-trihydroxyflavone-7-O-D-glucuronic acid, also known as scutellarin or scutellarin (structure such as Figure 1 It has the functions of reducing cerebrovascular resistance, improving cerebral blood circulation, increasing cerebral blood flow and anti-platelet aggregation. At present, 5,6,4'-trihydroxyflavone-7-O-D-glucuroni...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07H17/07C07H1/00A61K31/7048A61P9/00A61P7/02
CPCY02P20/55
Inventor 何正有刘君焱杨放姚洁李蔷薇熊伟张建强邓小宽
Owner 四川抗菌素工业研究所有限公司
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