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Intermediate of flavonoid compound and preparation method and application thereof

A technology of flavonoids and compounds, applied in sugar derivatives, organic chemistry, drug combination, etc., can solve the problems of low extraction efficiency, difficult to meet research applications, complex and cumbersome operations for separating and extracting compounds of formula A

Inactive Publication Date: 2012-05-23
SHANGHAI INST OF PHARMA IND CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0008] The technical problem to be solved by the present invention is to provide a new intermediate compound for synthesizing the compound of formula A in order to overcome the existing complex and cumbersome operation of separating and extracting the compound of formula A from plants, the extraction efficiency is low, and it is difficult to meet the needs of research and application. Its preparation method, and its application in the preparation formula A compound

Method used

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  • Intermediate of flavonoid compound and preparation method and application thereof
  • Intermediate of flavonoid compound and preparation method and application thereof
  • Intermediate of flavonoid compound and preparation method and application thereof

Examples

Experimental program
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Effect test

preparation example Construction

[0055] Preparation of formula M compound:

[0056] Reference example 1 5,7, the synthesis of 4 '-O-trihexanoyl apigenin (formula M compound, R 1 for -CO(CH 2 ) 4 CH 3 )

[0057] Apigenin (Formula G, R 1 for -CO(CH 2 ) 4 CH 3 , 1.08g, 4mmol), 4-dimethylaminopyridine (155mg, 1.2mmol), triethylamine (2.6ml, 20mmol,) were dissolved in 10ml of dimethylformamide, hexanoyl chloride (3.2ml, 22.8mmol), stirred and reacted at 25°C for 8 hours (TLC detection apigenin was consumed), the system was diluted with dichloromethane, the organic phase was washed twice with saturated brine, dried over anhydrous sodium sulfate, filtered and collected the organic phase, After concentration, the crude product was recrystallized from ethanol to obtain a white solid (1.95 g, yield 88%).

[0058] 1 H NMR (400MHz, CDCl3) δ: 0.91(m, 9H); 1.34(m, 12H); 1.75(m, 6H); 2.57(m, 4H); 2.76(d, 2H); 6.62(s, 1H) ;6.83(s,1H);7.26(d,2H);7.33(s,1H);7.88(d,2H)

[0059] MS: 565(M+H); 1151(2M+Na)

[0060] Re...

Embodiment 1

[0067] Embodiment 1 5, the synthesis of 4'-dihexanoyl-pigenin (compound of formula L, R 1 =-CO(CH 2 ) 4 CH 3 )

[0068] Formula M (n=4, 2g, 3.54mmol), dissolved in 50ml of dichloromethane and 50ml of methanol, was added potassium carbonate (242mg, 1.77mmol) at 0°C, naturally heated to 20°C, and reacted for 3 hours (TLC detection formula M was consumed), neutralized by adding 2mol / L hydrochloric acid / methanol solution, concentrated the reaction solution, and purified by silica gel column chromatography (dichloromethane:acetone=40:1) to obtain a white solid (1.52g, 92%).

[0069] 1 H-NMR (400MHz, CDCl 3 ): δ8.52(s, 1H), 7.74(d, 2H, J=8.4Hz), 7.17(d, 2H, J=8.8Hz), 6.71(d, 1H, J=2.4Hz), 6.51(d , 1H, J=2.8Hz), 6.50(s, 1H), 2.71(t, 2H, J=7.2Hz), 2.56(t, 2H, J=7.6Hz), 1.78(m, 4H), 1.39(m , 8H), 0.93(m, 6H)

[0070] 13 C-NMR (100MHz, CDCl 3 ): δ177.7, 173.5, 172.3, 162.4, 161.9, 158.9, 153.6, 150.7, 128.6, 127.7, 127.6, 122.6, 122.5, 110.4, 109.9, 107.6, 101.7, 34.6, 34.5, 3...

Embodiment 2

[0072] Embodiment 2 5, the synthesis of 4'-dihexanoyl-pigenin (compound of formula L, R 1 =-CO(CH 2 ) 4 CH 3 )

[0073] Formula M (n=4, 2g, 3.54mmol), dissolved in 25ml of dichloromethane and 25ml of methanol, was added potassium carbonate (242mg, 1.77mmol) at 0°C, naturally heated to 20°C, and reacted for 3 hours (TLC detection formula M was consumed), neutralized by adding 2mol / L hydrochloric acid / methanol solution, concentrated the reaction solution, and purified by silica gel column chromatography (dichloromethane:acetone=40:1) to obtain a white solid (1.45g, 88%).

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Abstract

The invention discloses an intermediate of a flavonoid compound shown in a formula K and a preparation method thereof. In the heterogeneous solution of a non-protonic solvent and water, under the action of an alkaline reagent and a phase transfer catalyst, the compound shown in the formula L reacts with 2,3,4,6-tetraphenyl formyloxy bromo-glucose shown in the formula H, wherein R1 is -CO(CH2)nCH3or benzoyl; n ranges from 0 to 8; and Bz is the benzoyl. The invention also relates to application of the intermediate of the flavonoid compound shown in the formula K in preparation of the flavonoidcompound shown in the formula A. Compared with the conventional method for separating and extracting the flavonoid compound shown in the formula A from the plant, the method for preparing the flavonoid compound shown in the formula A from the intermediate of the flavonoid compound shown in the formula K can realize large-scale industrialized production, and has the advantages of simple steps, no special reagent or harsh requirements on reaction conditions, and high yield and purity.

Description

technical field [0001] The invention relates to a class of flavonoid compound intermediates and a preparation method and application thereof. Background technique [0002] Common ischemic diseases include coronary heart disease, cerebral insufficiency, cerebral infarction and other heart and cerebrovascular ischemic diseases, which are one of the main diseases that endanger human health. Ischemic cerebrovascular diseases account for 50-70% of all cerebrovascular diseases, and are characterized by high morbidity, high mortality and high disability rate. health. [0003] Apigenin 7-O-β-D-glucoside-4`-O-α-L-rhamnoside (Formula A) (English name: apigenin-7-O-β-D-glucopyranosyl-4`-O- α-L-rhamnopyranosid) is a flavonoid compound, which can be extracted and isolated from Ranunculus genus plants, such as Ranunculus sieboldii and R. sceleratus, and has certain anti-tumor, anti-HBV and The role of HSV-1. (Pan Yunxue, Study on the Chemical Constituents of Ranunculus chinensis, Chine...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07H17/07C07H15/26A61P9/10
CPCY02P20/55
Inventor 林峰姚林高祺陈建丽
Owner SHANGHAI INST OF PHARMA IND CO LTD
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