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, sugar derivatives, sugar derivatives, etc., can solve the problems of long synthetic routes and low yields

Inactive Publication Date: 2012-02-29
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 1.84g of 3,4,5-trimethoxyphenol, 2.7g of p-methoxycinnamic acid chloride, put into 20mL BF 3 -Et 2 O solution, make it fully dissolved, add 2g 4A molecular sieves, heat and reflux for 15 minutes, stop heating, filter, and recrystallize with petroleum ether-ethyl acetate (3:1) to obtain 9-hydroxyl-5,6,7,4 '-tetramethoxychalcone 3.13g, the transfer rate of this step is 91%.

[0017] Take 3.44g of 9-hydroxy-5,6,7,4'-tetramethoxychalcone, 200mg of iodine, dissolve in 25mL of DMSO, reflux for 2 hours, then carefully pour into 200g of crushed ice, filter and precipitate with 20% Na 2 SO 3 Wash and recrystallize with petroleum ether-ethyl acetate (10:1) to obtain 2.98 g of 5,6,7,4'-tetramethoxyflavone with a transfer rate of 87%.

[0018] Take 3.42g of 5,6,7,4'-tetramethoxyflavone, add 5ml of 47% HBr, 10ml of glacial acetic acid, mix well, heat to reflux for 18 hours, then pour 200g of crushed ice carefully to obtain a yellow precipitate. The precipitate was collecte...

Embodiment 2

[0025] Purification of target product

[0026] Take 100g of the finished product, add 1000mL of pure water, adjust the pH value to 7 with 30% sodium hydroxide solution, make it completely dissolved, filter, add 8 times acetone to the filtrate at 25°C for precipitation, and stir while adding acetone , to make the precipitation complete, let 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, then add 25% hydrochloric acid to adjust the pH value to 1 ~2, let stand for 10 hours, filter with suction, wash with water until neutral, wash with ethanol once, and dry to obtain the refined product. According to HPLC analysis, the content of 5,6,4'-trihydroxyflavone-7-O-D-glucuronic acid in the obtained sample was 99.25%.

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Abstract

The invention discloses 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 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] In natural medicines, flavones are the most common flavonoids, accounting for more than a quarter of the total flavonoids, and have obvious structural diversity. It has been found that flavonoids have a variety of physiological activities, mainly including: anti-cardiovascular and cerebrovascular diseases, anti-inflammation, anti-hepatic virus, liver protection, antibacterial, anti-cancer, anti-oxidation and other effects. Among them, 5,6,4'-trihydroxyflavone-7-O-D-glucuronic acid, also known as scutellarin or scutellarin, has a structure such as Figure 1 As shown), it has the effects 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-glucuro...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07H17/07C07H1/00
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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