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Split heterocyclic 23-hydroxybetulinic acid derivatives and preparation method, preparation and application thereof

A kind of derivative, betulinic acid technology, applied in the field of natural medicine and medicinal chemistry

Inactive Publication Date: 2010-11-10
CHINA PHARM UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0011] At present, in the field of anti-tumor, most researchers believe that betulinic acid and its derivatives achieve the purpose of anti-tumor by inhibiting angiogenesis, but no such compounds have entered the clinical trial stage for many years

Method used

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  • Split heterocyclic 23-hydroxybetulinic acid derivatives and preparation method, preparation and application thereof
  • Split heterocyclic 23-hydroxybetulinic acid derivatives and preparation method, preparation and application thereof
  • Split heterocyclic 23-hydroxybetulinic acid derivatives and preparation method, preparation and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0081] 23-tert-butyldimethylsilyloxy-lupine-20(29)-en-28-oic acid benzyl a[3,2-b]pyrazine

[0082] Dissolve 3-carbonyl-23-tert-butyldimethylsilyloxy-lupine-20(29)-en-28-oic acid benzyl ester (0.6g, 0.89mmol) in morpholine (25ml) and add sulfur (0.32g, 10mmol) and ethylenediamine (0.28g, 4.5mmol), refluxed for 4h, diluted with ethyl acetate (30ml), washed three times with water, washed twice with saturated brine, dried over anhydrous sodium sulfate, filtered, concentrated, column Chromatography (petroleum ether: ethyl acetate = 20:1) gave a white solid (0.43 g, 68%). ESI-MS m / z: 711.5[M+H] +

Embodiment 2

[0084] 23-Hydroxy-lupine-20(29)-en-28-oic acid benzyl[3,2-b]pyrazine

[0085] Dissolve 23-tert-butyldimethylsilyloxy-lupin-20(29)-ene-28-oate benzyl[3,2-b]pyrazine (0.4g, 0.56mmol) in acetone (30ml ), add 10% hydrochloric acid (2ml), stir at room temperature for 2 hours, dilute with ethyl acetate, wash with water until neutral, wash with saturated brine, dry over anhydrous sodium sulfate, filter, concentrate, column chromatography (petroleum ether: ethyl acetate =2:1), a white solid (0.30g, 91%) was obtained, mp 118-121°C. IR (film, cm -1 )3438, 3069, 2951, 2871, 1727, 1644, 1456, 1407, 1379, 1171, 1156, 1130, 885, 699; 1 H-NMR (CDCl 3 , 300MHz): δ0.84, 0.99, 1.30, 1.70 (6H for 0.84, each 3H for others, s, 24, 25, 26, 27 and 30-CH 3 ), 2.22-2.31(2H, m), 2.44(1H, d, J=16.9Hz, H-1a), 3.03(1H, m, H-19), 3.08(1H, d, J=16.7Hz, H -1b), 3.47, 3.79 (each 1H, d, J=10.5Hz, H-23), 4.63, 4.75 (each 1H, s, H-29), 5.13 (2H, dd, J=22.7, 12.3Hz, CH 2 -Ar), 7.31-7.38 (5H, m, H-Ar), 8.35,...

Embodiment 3

[0087] 23-Acetoxy-lupine-20(29)-en-28-oic acid benzyl[3,2-b]pyrazine

[0088] 23-Hydroxy-lupine-20(29)-ene-28-acid benzyl[3,2-b]pyrazine (0.25g, 0.43mmol) was dissolved in pyridine (10ml), and acetic anhydride (2ml ), stirred at room temperature for 10h, diluted with ethyl acetate (25ml), washed with 10% hydrochloric acid until acidic, washed twice with water, washed with saturated sodium bicarbonate until no bubbles were produced, dried over anhydrous sodium sulfate, filtered, concentrated, column chromatography (petroleum ether:ethyl acetate=6:1) to obtain a white solid (0.23g, 86%).

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Abstract

The invention relates to the medicinal chemistry field, in particular to derivatives containing heterocyclic 23-hydroxybetulinic acid. The invention also discloses a preparation method of the derivatives, medicine compositions containing the compound and application of the compound on treating tumor diseases or symptoms.

Description

technical field [0001] The invention relates to the fields of natural medicine and medicinal chemistry, in particular to a class of modified 23-hydroxy betulinic acid derivatives. The invention also discloses the preparation method of these 23-hydroxy betulinic acid derivatives, the pharmaceutical composition containing these 23-hydroxy betulinic acid derivatives and the anti-tumor application of these 23-hydroxy betulinic acid derivatives. Background technique [0002] 23-Hydroxybetulinic acid is a compound similar to betulinic acid in structure. 23-Hydroxybetulinic acid is a pentacyclic triterpenoid compound extracted from the Chinese herbal medicine Pulsatilla chinensis Regel. Belonging to the genus Pulsatilla in the family Ranunculaceae, it has the effects of clearing heat and detoxifying, cooling blood and stopping dysentery, drying dampness and killing insects. Clinically, it is mainly used to treat bacillary dysentery, amoebic dysentery, and gynecological vaginitis. ...

Claims

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Application Information

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IPC IPC(8): C07J71/00A61K31/58A61K31/7056A61K31/706A61P35/00A61P35/02
Inventor 吴晓明徐进宜朱培清姚和权李赞孙飞江波叶文才张陆勇查晓明袁胜涛
Owner CHINA PHARM UNIV
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