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Method for preparing flavonoid dimeric compound as well as medium and preparation method thereof

A technology for flavonoids and intermediates, which is applied in the new synthesis field, can solve the problems of long route, complicated and tedious operation, low total yield and the like, and achieves the effects of simple operation, high yield and short route.

Inactive Publication Date: 2011-08-17
SHANGHAI INST OF PHARMA IND CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] The technical problem to be solved by the present invention is to overcome the shortcomings of the existing synthetic method for preparing flavonoid dimers shown in formula D, such as long route, complex and cumbersome operation, and low total yield, and provide a method with simpler operation, A method for synthesizing the flavonoid dimer with a shorter route and a higher total yield, and providing a new intermediate compound used in the method and a preparation method thereof

Method used

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  • Method for preparing flavonoid dimeric compound as well as medium and preparation method thereof
  • Method for preparing flavonoid dimeric compound as well as medium and preparation method thereof
  • Method for preparing flavonoid dimeric compound as well as medium and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0055] Example 1 1,13-two (7-benzyl-5,4 '-dihydroxypigenin)-1,4,7,10,13-pentaoxo-tridecane (formula A compound (n= 4))

[0056] 7-benzyl-5,4'-dihydroxypigenin (142mg, 0.42mmol) was dissolved in dimethylformamide 3ml, potassium carbonate (283mg, 2.06mmol) was added, after stirring for ten minutes, formula C (n= 4, 72mg, 0.21mmol), react at 140~150°C for 3 hours (TLC detects that Formula C is consumed), cool, add 10ml of water, wash the water phase with dichloromethane (10ml×3), collect the dichloromethane phase and use saturated Wash the dichloromethane phase (20ml×3) with brine, dry over anhydrous sodium sulfate, collect the filtrate by filtration, and concentrate the filtrate to obtain a yellow solid formula A (n=4, 106mg) by column chromatography (dichloromethane:methanol=50:1) , 58%).

[0057] 1 H NMR (400MHz, CDCl3) δ: 3.68(m, 8H); 3.87(t, 4H); 4.16(t, 4H); 5.11(s, 4H); 6.40(d, 2H); 6.50(d, 4H) ;6.52(s,2H);6.97(d,4H);7.25(m,10H);7.75(d,4H);12.74(s,2H)

[0058] 13 C N...

Embodiment 2

[0060] Example 2 1,13-two (7-benzyl-5,4 '-dihydroxypigenin)-1,4,7,10,13-pentaoxo-tridecane (formula A compound (n= 4))

[0061] 7-benzyl-5,4'-dihydroxypigenin (142mg, 0.42mmol) was dissolved in dimethylacetamide 6ml, potassium carbonate (566mg, 4.06mmol) was added, and after stirring for ten minutes, formula C (n= 4, 110mg, 0.31mmol), react at 145-155°C for 3 hours (TLC detects that Formula C is consumed), cool, spin off acetone, add 10ml of water, wash the water phase with dichloromethane (10ml×3), collect dichloromethane Wash the dichloromethane phase (20ml×3) with saturated brine after the phase, dry over anhydrous sodium sulfate, filter and collect the filtrate, and column chromatography (dichloromethane:methanol=50:1) after the filtrate is concentrated to obtain a yellow solid formula A(n =4, 92 mg, 50%).

[0062] MS: 901 (M+Na)

Embodiment 3

[0063] Example 3 1,13-two (7-benzyl-5,4 '-dihydroxypigenin)-1,4,7,10,13-pentaoxo-tridecane (formula A compound (n= 4))

[0064] 7-benzyl-5,4'-dihydroxypigenin (142mg, 0.42mmol) was dissolved in 3ml of nitromethane, potassium carbonate (283mg, 0.42mmol) was added, after stirring for ten minutes, formula C (n=4, 72mg, 0.21mmol), react at 140-150°C for 3 hours (TLC detects that formula C is consumed), cool, add 10ml of water, wash the water phase with dichloromethane (10ml×3), collect the dichloromethane phase and wash with saturated saline The dichloromethane phase (20ml×3) was dried over anhydrous sodium sulfate, and the filtrate was collected by filtration. After the filtrate was concentrated, column chromatography (dichloromethane:methanol=50:1) gave yellow solid formula A (n=4, 87mg, 48 %).

[0065] MS: 901 (M+Na)

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Abstract

The invention discloses a compounding method for preparing a flavonoid dimeric compound of formula D. In the mixed solvent of non-protonic solvent and alcoholic solvent, under the action of catalytic hydrogenation reaction catalyst, the compound of formula A is debenzylated by catalytic hydrogenation reaction, and the flavonoid dimeric compound of formula D can be prepared, wherein n is equal to1 to 9, and Bn is the phenmethyl. The invention also discloses a novel medium compound A used for the method and a preparation method thereof. Compared with the prior method for synthesizin the flavonoid dimeric compound sof formula D, the method has the advantages of simpler operation, shorter route and higher yield.

Description

technical field [0001] The present invention relates to a new synthesis method of a class of pharmaceutically active compounds, intermediates used and preparation methods thereof, in particular to a new synthesis method of a class of flavonoid dimers, intermediates used and preparation methods thereof. Background technique [0002] The multidrug resistance (multidrug resistance) of tumor cells to anticancer drugs has become the most serious obstacle to the success of chemotherapy. A series of flavonoid dimer compounds (formula D) reported in J. Med. Chem. 2006, 49, 6742-6759 have a strong inhibitory effect on multidrug resistance (MDR) of cancer cells. The compound is used in combination with other chemotherapeutic drugs, and has strong cytotoxicity to drug-resistant leukemia cells, breast cancer cells, and the like. Among them, the compound of formula D (n=4) has the strongest activity. [0003] [0004] Among them, n=1-9. [0005] Existing synthetic methods for prepa...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): A61P35/00C07D311/36
Inventor 林峰高祺连高焱陈建丽
Owner SHANGHAI INST OF PHARMA IND CO LTD
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