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Preparation method of 5,4'-dihydroxy flavone-7-O-D-glucuronic acid

A technology of glucuronic acid and dihydroxyflavone is applied in the field of preparation of 5,4'-dihydroxyflavone-7-O-D-glucuronic acid, which can solve the problems of long synthesis route, difficult extraction, high price, etc. The effect of few steps, simple and easy operation, and cheap and easy-to-obtain starting materials

Active Publication Date: 2015-07-08
KPC PHARM INC
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] But at present, there are few reports on the synthesis of 5,4'-dihydroxyflavone-7-0-D-glucuronic acid at home and abroad.
Commercially available 5,4'-dihydroxyflavone-7-0-D-glucuronic acid is derived from plant extracts, but since 5,4'-dihydroxyflavone-7-0-D-glucuronic acid is Very low content in mesodium, difficult to extract, therefore, the price is very high
However, the existing synthesis process has a relatively long synthetic route, and a large and expensive noble metal catalyst is used in the glycosidation step, which is not conducive to industrial production.

Method used

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  • Preparation method of 5,4'-dihydroxy flavone-7-O-D-glucuronic acid
  • Preparation method of 5,4'-dihydroxy flavone-7-O-D-glucuronic acid

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Experimental program
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Effect test

Embodiment 1

[0081] The preparation of structure compound shown in embodiment 1 formula I

[0082] 1) Preparation of structural compounds shown in formula III

[0083] The reaction equation is as follows:

[0084]

[0085] Wherein, in the compound of formula III, R is a methyl group.

[0086] Add 5.4g (20mmol) of apigenin, 22mL of acetic anhydride (d=1.08g / ml, 233mmol) and 27mL of pyridine in a dry and clean 150mL three-necked round-bottom flask equipped with a condenser, and heat to about 140°C to make The reaction was carried out under reflux for about 8 hours, and the raw materials were detected by TLC to have completely reacted. Stop heating, and when the temperature drops to about 50°C to 70°C, add 60 mL of ethyl acetate, stir and crystallize, filter with suction, wash the filter cake with ethyl acetate, and obtain a white flocculent solid 5,7,4'-tri The acetoxyflavone, namely the compound of formula III, was dried to obtain 6.7 g, with a yield of 90.8%.

[0087] 1 HNMR(500MHz...

Embodiment 2

[0100]The preparation of structure compound shown in embodiment 2 formula I

[0101] 1) Preparation of structural compounds shown in formula III

[0102] The reaction equation is as follows:

[0103]

[0104] Wherein, in the compound of formula III, R is phenyl.

[0105] Add 80g of pyridine hydrochloride to a 500ml round-bottomed flask, heat to about 140°C to dissolve, add 10g (37mmol) apigenin, and slowly add 70mL of benzoyl chloride (d=1.212, 600mmol) while stirring, and heat to 200°C The reaction was refluxed for about 9 hours. TLC 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 5,7,4'-tribenzoyloxyflavone as an off-white solid. After drying, recrystallize with ethanol to obtain 19.2g of pure 5,7,4'-tribenzoyl...

Embodiment 3

[0118] The preparation of structure compound shown in embodiment 3 formula I

[0119] 1) Preparation of structural compounds shown in formula III

[0120] The reaction equation is as follows:

[0121]

[0122] Wherein, in the compound of formula III, R is a methyl group.

[0123] Dissolve 5.4g (20mmol) of apigenin in 30ml of pyridine, slowly add 25mL of acetic acid (d=1.049g / ml, 437mmol) under stirring at room temperature, heat to 180°C and reflux for about 8 hours, TLC detects that the reaction is complete, and the reaction solution When it 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 5,7,4'-triacetoxyflavone as an off-white solid. After drying, it was recrystallized with ethanol to obtain 6.4 g of pure 5,7,4'-triacetoxyflavone (ie, the structural compound shown in formula III...

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Abstract

The invention relates to the drug synthesis technical field, and in particular, relates to a preparation method of 5,4'-dihydroxy flavone-7-O-D-glucuronic acid. The method comprises the following steps: taking a compound having a structure represented by the formula II, and under an alkaline condition, acylating to obtain a compound having a structure represented by the formula III; taking the compound having the structure represented by the formula III and alpha-bromo triacetoxy methyl glucuronate, and carrying out a glycosylation reaction, to obtain a compound having a structure represented by the formula IV; taking the compound having the structure represented by the formula IV, and hydrolyzing under an acidic condition, to obtain a compound having a structure represented by the formula V; and taking the compound having the structure represented by the formula V, hydrolyzing under an alkaline condition, and thus obtaining the product. The method provided by the invention has the advantages of cheap and easily obtained starting raw materials, less reaction steps, and simple and easily operated process, and is suitable for large-scale industrialized production; and through testing, the purity of the obtained product can reach more than 98%, and the total yield reaches up to 56%.

Description

technical field [0001] The invention relates to the technical field of drug synthesis, in particular to a preparation method of 5,4'-dihydroxyflavone-7-O-D-glucuronic acid. Background technique [0002] 5,4'-dihydroxyflavone-7-O-D-glucuronic acid, also known as breviscapine (apigenin-7-O-β-D-glucuronide), is derived from the plant Asteraceae breviscapita (also known as breviscapine) A flavonoid glycoside compound extracted from [Erigeron breviscapus (Vant.) Hand-Mazz], which has a structure shown in formula I, is distributed in various natural medicinal plants (such as: Erigeron breviscapus, bitter Dish, grass, mulberry leaves, sycamore leaves, daisies, etc.). The total ketone of 5,4'-dihydroxyflavone-7-0-D-glucuronic acid and scutellarin becomes breviscapine, which can reduce cerebrovascular resistance, improve cerebral circulation, relieve arterial spasm, improve brain-blood barrier, Anti-aging and other effects. [0003] [0004] At present, there are few reports on...

Claims

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Application Information

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IPC IPC(8): C07H17/07C07H1/00
Inventor 李鹏辉张志朋张伟杨兆祥
Owner KPC PHARM INC
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