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Method for preparing flavonoid compounds, used intermediate and preparation method thereof

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

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

AI Technical Summary

Problems solved by technology

[0009] The technical problem to be solved by the present invention is to provide a new method for synthesizing the compound of formula A and its Novel intermediates and methods for their preparation

Method used

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  • Method for preparing flavonoid compounds, used intermediate and preparation method thereof
  • Method for preparing flavonoid compounds, used intermediate and preparation method thereof
  • Method for preparing flavonoid compounds, used intermediate and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

preparation example Construction

[0105] Preparation of formula M compound:

[0106] Reference example 15, the synthesis of 7,4 '-O-trihexanoyl apigenin (formula M compound, R 1 for -CO(CH 2 ) 4 CH 3 )

[0107] 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%).

[0108] 1 HNMR (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)

[0109] MS: 565(M+H); 1151(2M+Na)

...

Embodiment 15

[0128] Synthesis of embodiment 15-O-hexanoyl-7-O-benzyl-4'-hydroxypigenin (formula E compound, 1 =-CO(CH 2 ) 4 CH 3 )

[0129] 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 %).

[0130] 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)

[0131] 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....

Embodiment 25

[0133] The synthesis (formula E compound, R 1 =-CO(CH 2 ) 4 CH 3 )

[0134] 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 a method for preparing flavonoid compounds shown in formula A, which comprises the following step: performing dehydroxylation protecting group reaction of the compounds shown in a formula B in a mixed solvent of a non-protonic solvent and an alcohol solvent under the action of an alkaline reagent to form the flavonoid compounds shown in the formula A, wherein R1 is -CO (CH2)n CH3 or benzoyl, n is 0 to 8, and Bz is benzoyl. The invention also relates to a new intermediate compound shown in the formula B and a preparation method thereof. Compared with the conventional method for extracting the flavonoid compounds shown in the formula A by separating from plants, the synthesis method of the invention makes the large-scale industrialized production of the compounds become possible; and the method of the invention has simple steps, has no strict requirements on a special reagent and reaction conditions, and has higher yield and purity.

Description

technical field [0001] The invention relates to a preparation method of flavonoids, an intermediate used and a preparation method 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, Chinese ...

Claims

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Application Information

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IPC IPC(8): C07H17/07A61P9/10
CPCY02P20/55
Inventor 林峰姚林高祺陈建丽
Owner SHANGHAI INST OF PHARMA IND
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