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

A technology of glucuronic acid and trihydroxyflavone, applied in the preparation of sugar derivatives, chemical instruments and methods, sugar derivatives, etc., can solve the problems of harsh reaction conditions, expensive reaction reagents, cumbersome process operations, etc., and achieve short synthetic routes , the product is easy to purify, and the effect of shortening the reaction 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

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Experimental program
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Embodiment 1

[0050] 1. Preparation of 5,6,7,4'-tetra-pivaloyloxyflavone

[0051] 20g (70mmol) of 5,6,7,4'-tetrahydroxyflavone was dissolved in 120mL of pyridine, and 173mL 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 solution was cooled to about 70°C, 200 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 36.6 g of pure 5,6,7,4'-tetrapivaloyloxyflavone, a white solid, with a chromatographic purity of over 98.00% and a yield of 84%. 1H-NMR (400MHz, CDCl3), 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....

Embodiment 2

[0059] 1. Preparation of 5,6,7,4'-tetrabenzoyloxyflavone

[0060] 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 19.9 g of pure 5,6,7,4'-tetrabenzoyloxyflavone, an off-white product, with a chromatographic purity of over 98.0% and a yield of 81%. 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

[0066] 1. Preparation of 5,6,7,4'-tetraacetoxyflavone

[0067] 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, CDCl3), 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).

[0068] 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 three-step reactions including acylation reaction, glycosylation reaction and acid neutralization reaction after alkaline hydrolysis reaction, 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 invention belongs to the field of drug synthesis, in particular to a method for preparing 5,6,4'-trihydroxyflavone-7-0-D-glucuronic acid. Background technique [0002] 5,6,4'-trihydroxyflavone-7-0-D-glucuronic acid, also known as scutellarin and scutellarin, is the whole plant of Erigeron breviscapus (Erigeron breviscapus) in the family Asteraceae. The main active ingredient of the flavonoid mixture extracted from Erigeron breviscapus, the molecular formula is C 21 h 18 o 12 , molecular weight is 462.37, and its structural formula is as shown in formula I: [0003] [0004] Clinical studies have shown that 5,6,4'-trihydroxyflavone-7-0-D-glucuronic acid has a significant effect on hypertension, cerebral hemorrhage, cerebral thrombosis, cerebral embolism multiple neuritis, chronic arachnoiditis and its sequelae Good curative effect, and also has certain curative effect on rheumatism, coronary heart disease. In addition, a large number of stud...

Claims

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Application Information

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IPC IPC(8): C07H17/07C07H1/00
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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