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Synthesis of related substances of 5,6,4'-trihydroxyflavone-7-0-d-glucuronic acid and its preparation method and application

A technology of glucuronic acid and trihydroxyflavone, which is applied in the preparation of sugar derivatives, sugar derivatives, sugar derivatives, etc., can solve the problems of no research and achieve the effects of simple operation, high product purity and short synthetic route

Active Publication Date: 2020-05-05
KPC PHARM INC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the impurity profile of the synthetic 5,6,4'-trihydroxyflavone-7-0-D-glucuronic acid is different from that of the currently marketed plant extract 5,6,4'-trihydroxyflavone-7-0-D-glucuronide There is no research on the related substances of 5,6,4'-trihydroxyflavone-7-0-D-glucuronic acid

Method used

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  • Synthesis of related substances of 5,6,4'-trihydroxyflavone-7-0-d-glucuronic acid and its preparation method and application
  • Synthesis of related substances of 5,6,4'-trihydroxyflavone-7-0-d-glucuronic acid and its preparation method and application
  • Synthesis of related substances of 5,6,4'-trihydroxyflavone-7-0-d-glucuronic acid and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0051] (1) Preparation of Compound III

[0052] 20g (27.4mmol) of 5,6,4'-triacetoxyflavone-7-O-D-methyl triacetoxyglucuronate was dissolved in 200mL of toluene, and then slowly added dropwise to 1,8-diazepine under stirring Dicycloundec-7-ene (DBU) 4.1g (27mmol), stirred at 30°C for about 8 hours to complete the reaction. About 500 ml of ethyl acetate was added to the reaction mixture with stirring, and washed twice with 500 ml of water. After the water layer was separated, an appropriate amount of anhydrous sodium sulfate was added to the organic layer to dry, and evaporated to dryness under reduced pressure. Silica gel column chromatography and elution with petroleum ether: ethyl acetate = 5:1 (v / v) eluent gave 15 g of white solid compound III with a chromatographic purity of over 98.00% and a yield of 82%.

[0053] 1 H-NMR (400MHz, DMS0), δ (ppm): 7.95 (2H, d, J = 8.6Hz), 7.51 (1H, s), 7.32 (2H, d, J = 8.6Hz), 6.78 (1H, s ),6.15(1H,d,J=7.8Hz),5.57(1H,d,J=10Hz), 5.38(1H,...

Embodiment 2

[0060] (1) Preparation of Compound III

[0061] 20g (27.4mmol) of 5,6,4'-triacetoxyflavone-7-O-D-methyl triacetoxyglucuronate was dissolved in 200mL of dichloromethane, then slowly added 4-dimethylaminopyridine under stirring (DMAP) 1.7g (13.7mmol, 0.5eq), stirred at 25°C for about 10 hours and the reaction was complete. About 300 ml of ethyl acetate was added to the reaction mixture with stirring, and it was washed twice with 500 ml of water. After the water layer was separated, an appropriate amount of anhydrous sodium sulfate was added to the organic layer to dry, and evaporated to dryness under reduced pressure. Silica gel column chromatography and elution with petroleum ether: ethyl acetate = 5:1 (v / v) eluent gave 14.3 g of white solid compound III with a chromatographic purity of over 98.00% and a yield of 78%. The NMR identification result is consistent with the result of Example 1.

[0062] (2) Preparation of 5,6,4'-trihydroxyflavone-7-0-D-glucuronic acid related su...

Embodiment 3

[0065] (1) Preparation of Compound III

[0066] 20g (27.4mmol) of 5,6,4'-triacetoxyflavone-7-O-D-methyl triacetoxyglucuronate was dissolved in 200mL of tetrahydrofuran, and then 6.5g (82.2mmol) of pyridine was added dropwise under stirring, The reaction was stirred at 25°C for about 6 hours and the reaction was complete. About 200ml of ethyl acetate was added to the reaction mixture under stirring, and washed twice with 500°C water. After the water layer was separated, an appropriate amount of anhydrous sodium sulfate was added to the organic layer to dry, and evaporated to dryness under reduced pressure. Silica gel column chromatography and elution with petroleum ether: ethyl acetate = 5:1 (v / v) eluent gave 14.7 g of white solid compound III with a chromatographic purity of over 98.00% and a yield of 80%. The NMR identification result is consistent with the result of Example 1.

[0067] (2) Preparation of 5,6,4'-trihydroxyflavone-7-0-D-glucuronic acid related substance b ...

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Abstract

The invention relates to a 5,6,4'-trihydroxyl flavone-7-O-D-glucuronic acid related substance b which is successfully prepared through selective elimination and hydrolysis by taking 5,6,4'-triacetoxy flavone-7-O-D-triacetyl methyl glucuronate (the structural formula is as shown in a formula II) as a raw material. The related substance b is further purified, and finally, a 5,6,4'-trihydroxyl flavone-7-O-D-glucuronic acid related substance b monomer is obtained to obtain a related substance chemical structure after confirmation. The method is short in synthetic route, low in cost, simple to operate, accurate in result, high in product purity, high in reaction yield and easy for product purification, and can be used for impurity analysis and control of a synthesized 5,6,4'-trihydroxyl flavone-7-O-D-glucuronic acid sample, so that quality control of the synthesized 5,6,4'-trihydroxyl flavone-7-O-D-glucuronic acid is facilitated, and the product quality is better guaranteed.

Description

technical field [0001] The invention relates to the technical field of medicinal chemistry, in particular to a compound related to the synthesis of 5,6,4'-trihydroxyflavone-7-0-D-glucuronic acid and its preparation method and application. 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 0 12 , the molecular weight is 462.37, and its structural formula is shown in formula IV: [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 effec...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07H17/07C07H1/00G01N30/02G01N30/06
CPCC07H1/00C07H17/07G01N30/02G01N30/06
Inventor 李鹏辉杨兆祥董知旭黄照昌
Owner KPC PHARM INC
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