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Method for preparing 5,6,4'-trihydroxy flavone-7-0-D-glucuronic acid

A technology of glucuronic acid and trihydroxyflavone is applied in the preparation of sugar derivatives, chemical instruments and methods, sugar derivatives, etc., and can solve the problems of expensive reaction reagents, cumbersome process operations, harsh reaction conditions, etc. The effect of shortening the reaction route and shortening the synthesis route

Active Publication Date: 2013-10-30
KPC PHARM INC
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] In view of this, the object of the present invention is to aim at the synthesis method route of 5,6,4'-trihydroxyflavone-7-0-D-glucuronic acid in the prior art, long route, low yield, expensive reaction reagent and large consumption , The defects of cumbersome process operation and harsh reaction conditions provide a method for preparing 5,6,4'-trihydroxyflavone-7-0-D-glucuronic acid with short synthetic route, high yield and low cost

Method used

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  • Method for preparing 5,6,4'-trihydroxy flavone-7-0-D-glucuronic acid
  • Method for preparing 5,6,4'-trihydroxy flavone-7-0-D-glucuronic acid
  • Method for preparing 5,6,4'-trihydroxy flavone-7-0-D-glucuronic acid

Examples

Experimental program
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Effect test

Embodiment 1

[0057] 1. Preparation of 5,6,7,4'-tetra-pivaloyloxyflavone

[0058] 10g (70mmol) of 5,6,7,4'-tetrahydroxyflavone was dissolved in 60mL of pyridine, and 86mL of pivaloyl chloride (d=0.976g / mL, 1.4mol) was slowly added dropwise at room temperature, and heated to 130°C for reflux reaction 6 After ~8 hours, TLC detected that the reaction was complete. When the reaction liquid was cooled to about 70°C, 100 mL of ethyl acetate was added, and a large amount of white solid gradually precipitated. Stirring was continued for 1 hour, cooled to room temperature, and left overnight in the refrigerator. Filtration gave 5,6,7,4'-tetrapivaloyloxyflavone as an off-white solid. After drying, it was recrystallized with ethanol to obtain 18 g of pure 5,6,7,4'-tetrapivaloyloxyflavone, a white product with a chromatographic purity of over 98.00% and a yield of 84%. 1H-NMR (400MHz, CDC13), δ (ppm): 7.75 (2H, d, J = 8.6Hz), 7.13 (1H, s), 7.12 (2H, d, J = 8.6Hz), 6.48 (1H, s ), 1.59(9H, s), 1.54(9H...

Embodiment 2

[0068] 1. Preparation of 5,6,7,4'-tetrabenzoyloxyflavone

[0069] Dissolve 10g (35mmol) of 5,6,7,4'-tetrahydroxyflavone in 70mL of pyridine, slowly add 81mL of benzoyl chloride (d=1.212, 700mmol) under stirring at room temperature, heat to 180°C and reflux for about 9 hours, TLC It was detected that the reaction was complete. When the reaction solution was cooled to about 70°C, 90 mL of ethyl acetate was added, and a large amount of white solids gradually precipitated. Stirring was continued for 1 hour, cooled to room temperature, and left overnight in the refrigerator. Filtration afforded 5,6,7,4'-tetrabenzoyloxyflavone as an off-white solid. After drying, it was recrystallized with ethanol to obtain 21.4 g of pure 5,6,7,4'-tetrabenzoyloxyflavone, an off-white product, with a chromatographic purity of over 98.0% and a yield of 87%. 1H-NMR (400MHz, DMSO), δ (ppm): 8.56 (2H, d, J = 8.9Hz), 8.55 (2H, d, J = 8.9Hz), 8.54 (2H, d, J = 8.9Hz), 8.52 (2H, d, J = 8.9Hz), 8.10 (2H, d...

Embodiment 3

[0077] 1. Preparation of 5,6,7,4'-tetraacetoxyflavone

[0078] Dissolve 10g (35mmol) of 5,6,7,4'-tetrahydroxyflavone in 50mL of pyridine, slowly add 30mL of acetic anhydride (d=1.08, 400mmol) dropwise at room temperature, heat to 140°C and reflux for 4-5 hours, TLC The detection reaction is complete. When the reaction solution was cooled to about 70°C, 90 mL of ethyl acetate was added, and a large amount of white solid gradually precipitated. Stirring was continued for 1 hour, cooled to room temperature, and left overnight in the refrigerator. Filtration afforded 5,6,7,4'-tetraacetoxyflavone as an off-white solid. After drying, it was recrystallized with ethanol to obtain 13.7 g of pure off-white 5,6,7,4'-tetraacetoxyflavone, with a chromatographic purity of over 98.00% and a yield of 86%. 1H-NMR (400MHz, CDC13), δ (ppm): 7.64 (2H, d, J = 8.7Hz), 7.03 (1H, s), 7.02 (2H, d, J = 8.6Hz), 6.39 (1H, s ), 2.21(3H, s), 2.14(3H, s), 2.12(3H, s), 2.11(3H, s).

[0079] 2. Preparati...

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Abstract

The invention relates to the field of drug synthesis and discloses a method for preparing 5,6,4'-trihydroxy flavone-7-0-D-glucuronic acid. The method is characterized by taking 5,6,7,4'-tetrahydroxy flavone as a raw material, adopting a brand-new synthetic route and carrying out acylation reaction, glycosylation reaction and two-step hydrolysis reactions, thus preparing high-purity 5,6,4'-trihydroxy flavone-7-0-D-glucuronic acid. The preparation method has the advantages of short synthetic route, low cost, high reaction yield and easiness in product purification, and is suitable for industrial production of 5,6,4'-trihydroxy flavone-7-0-D-glucuronic acid.

Description

Technical field [0001] The present invention is a method of drug synthesis, and especially involves a method for preparing 5,6,4'-trimetroxylkyelskones-7-0-D-glycosachalic acid. Background technique [0002] 5,6,4'-trihaylooflavonoids-7-0-D-glucosol acid, also known as lamp Blossin, wild scutelinin, is a whole grass (Ericeron Breviscapus) from the chrysanthemums of the chrysanthemum.The main effective ingredients of the flavonoid mixture extracted in the lamp in Asarum), the molecular formula is C 21 H 18 O 12 , The molecular weight is 462.37, the structure formula is shown in the formula I: [0003] [0004] Clinical studies have shown that 5, 6, 4'-trioneofzel-7-0-D-glucosolic acid forms hypertension, cerebral hemorrhage, cerebral thrombosisGood efficacy, and has certain effects on rheumatism and coronary heart disease.In addition, a large number of studies have confirmed that 5,6,4'-trihaytroxylofen-7-0-D-glucosolic acid has anti-inflammatory, antioxidant, protein kinase inh...

Claims

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Application Information

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IPC IPC(8): C07H17/07C07H1/00
CPCC07H17/07C07H1/00
Inventor 李鹏辉张伟杨兆祥张雄波王珺朱海贝陈锦锌白奕阳
Owner KPC PHARM INC
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