Intermediate of flavonoid compound and preparation method and application thereof

A technology for flavonoids and compounds, which is applied in the fields of sugar derivatives, organic chemistry, drug combinations, etc., can solve the problems of low extraction efficiency, difficulty in meeting research applications, complicated and tedious operations for separating and extracting compounds of formula A, etc.

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

Problems solved by technology

[0009] 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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preparation example Construction

[0071] Preparation of compound of formula M:

[0072] Reference Example 15, Synthesis of 7,4`-O-trihexanoyl apigenin (compound of formula M, R 1 For -CO(CH 2 ) 4 CH 3 )

[0073] 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, and hexanoyl chloride (3.2ml, 22.8mmol), the reaction was stirred at 25°C for 8 hours (the apigenin was consumed by TLC), 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%).

[0074] 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)

[0075] MS: 565 (M+H); 1151 (2M+Na)

[0076] ...

Embodiment 15

[0094] Example 15 Synthesis of-O-hexanoyl-7-O-benzyl-4'-hydroxyapigenin (compound of formula E, R 1 =-CO(CH 2 ) 4 CH 3 )

[0095] 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 raised to 20°C and reacted for 8 hours. (TLC shows that formula F is consumed), add 1mol / L hydrochloric acid and methanol to neutralize, remove the solvent by rotary evaporation, and separate and purify by silica gel column chromatography (dichloromethane:acetone=30:1) to obtain a pale yellow solid (1.52g, 90.3) %).

[0096] 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); 6.73 (d, 1H) ); 7.06(d, 2H); 7.21(d, 1H); 7.36(m, 5H); 7.88(d, 2H), 9.02(s, 1H)

[0097] 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, 13...

Embodiment 25

[0099] Example 25 Synthesis of -O-hexanoyl-7-O-benzyl-4'-hydroxyapigenin (compound of formula E, R 1 =-CO(CH 2 ) 4 CH 3 )

[0100] Formula F (n=4, 2g, 3.5mmol) was dissolved in a mixed solvent of 7.5ml of dichloromethane and 7.5ml of methanol. After cooling to -10°C, sodium carbonate (53mg, 0.5mmol) was added and the temperature was raised to 30°C. React for 10 hours (TLC shows that formula F is consumed), add 1mol / L hydrochloric acid and methanol to neutralize, remove the solvent by rotary evaporation, and 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 C and a preparation method thereof. In the mixed solvents of a non-protonic solvent and an alcohol solvent, under the action of a catalyst for catalytic hydrogenation, the compound shown in the formula D undergoes catalytic hydrogenation to remove benzyl, wherein R1 is -CO(CH2)nCH3 or benzoyl; n ranges from 0 to 8; Bn is the benzyl; and Bz is the benzoyl. The invention also relates to application of the intermediate of the flavonoid compound shown in the formula C 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 C 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 cardiac and cerebrovascular ischemic diseases, which are one of the main diseases that endanger human health. Ischemic cerebrovascular diseases account for 50 to 70% of all cerebrovascular diseases, and have the characteristics of high morbidity, high mortality and high disability. In recent years, the incidence and mortality of this type of disease have been ranked first, seriously harming human beings. Health. [0003] Apigenin 7-O-β-D-glucopyranosyl-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 plants, such as Ranunculus sieboldii and R. sceleratus. It has certain...

Claims

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Application Information

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