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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 complex and cumbersome separation and extraction of compounds of formula A, low extraction efficiency, and difficult to meet research applications

Inactive Publication Date: 2010-05-26
SHANGHAI INST OF PHARMA IND CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

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

[0057] Preparation of formula M compound:

[0058] Reference example 15, the synthesis of 7,4 '-O-trihexanoyl apigenin (formula M compound, R 1 for -CO(CH 2 ) 4 CH 3 )

[0059] 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), stirring reaction under 25 ℃ of temperature 8 hours (TLC detects that apigenin is consumed), system is diluted with dichloromethane, organic phase is washed twice with saturated brine, dried over anhydrous sodium sulfate, filters and collects organic phase, After concentration, the crude product was recrystallized from ethanol to obtain a white solid (1.95 g, yield 88%).

[0060] 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)

[0061] MS: 565(M+H); 1151(2M+Na)

[0062] Refer...

Embodiment 1

[0080] Embodiment 1 The synthesis (formula E compound, R 1 =-CO(CH 2 ) 4 CH 3 )

[0081] Formula F (n=4, 2g, 3.5mmol) was dissolved in a mixed solvent of 15ml of dichloromethane and 15ml of methanol, after cooling to 0°C, potassium carbonate (69mg, 0.5mmol) was added, and the temperature was naturally raised to 20°C, and reacted for 8 hours (TLC shows that formula F is consumed), add 1mol / L hydrochloric acid methanol to neutralize, remove the solvent by rotary evaporation, separate and purify by silica gel column chromatography (dichloromethane: acetone=30:1) to obtain a light yellow solid (1.52g, 90.3 %).

[0082] 1 H NMR (400MHz, CDCl 3 )δ: 0.92(m, 3H); 1.39(m, 4H); 1.46(m, 2H); 2.67(t, 2H); 5.31(s, 2H); 6.49(s, 1H); ); 7.06(d, 2H); 7.21(d, 1H); 7.36(m, 5H); 7.88(d, 2H), 9.02(s, 1H) 13 C NMR (CDCl 3 )δ: 13.9, 22.3, 24.1, 31.3, 34.3, 99.9, 105.9, 108.9, 111.0, 116.1, 116.2, 122.2, 127.4, 127.5, 127.8, 128.7, 128.8, 135.3, 150.3, 158.6, 160.1, 162 , 177.0

[0083] M...

Embodiment 2

[0084] Example 2 Synthesis of 5-O-hexanoyl-7-O-benzyl-4'-hydroxypigenin (formula E compound, 1 =-CO(CH 2 ) 4 CH 3 )

[0085] Formula F (n=4, 2g, 3.5mmol) was dissolved in a mixed solvent of 7.5ml of dichloromethane and 7.5ml of methanol, cooled to -10°C, added sodium carbonate (53mg, 0.5mmol), and naturally rose to 30°C, React for 10 hours (TLC shows that formula F is consumed), add 1mol / L methanol hydrochloric acid to neutralize, remove the solvent by rotary evaporation, separate and purify by silica gel column chromatography (dichloromethane: acetone=30:1) to obtain a light yellow solid (1.40 g, 83.2%).

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Abstract

The invention discloses an intermediate of a flavonoid compound shown in a formula E and a preparation method thereof. In the mixed solvents of a non-protonic solvent and an alcohol solvent, under the action of an alkaline reagent, the compound shown in the formula F undergoes selective dehydroxylation protecting group reaction, wherein R1 is -CO(CH2)nCH3 or benzoyl; n ranges from 0 to 8; and Bn is the benzyl. The invention also relates to application of the intermediate of the flavonoid compound shown in the formula E in preparation of the flavonoid compound 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 E 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 Applications(China)
IPC IPC(8): C07D311/30C07H17/07A61P9/10
CPCY02P20/55
Inventor 林峰姚林高祺陈建丽
Owner SHANGHAI INST OF PHARMA IND CO LTD
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