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23-hydroxy betulinic acid derivative with modified sites 3, 23 and 28 as well as preparation method, preparation and application thereof

A hydroxyl and carbonyl technology, applied in the field of natural medicine and medicinal chemistry

Inactive Publication Date: 2014-05-07
CHINA PHARM UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] 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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  • 23-hydroxy betulinic acid derivative with modified sites 3, 23 and 28 as well as preparation method, preparation and application thereof
  • 23-hydroxy betulinic acid derivative with modified sites 3, 23 and 28 as well as preparation method, preparation and application thereof
  • 23-hydroxy betulinic acid derivative with modified sites 3, 23 and 28 as well as preparation method, preparation and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0057] 3,23-Dihydroxy-lupine-20(29)-en-28-oic acid benzyl ester

[0058] Dissolve 23-hydroxybetulinic acid (1.00g, 2.1mmol) in N,N-dimethylformamide (20mL), add potassium carbonate (1.00g, 7.2mmol), benzyl bromide (0.3ml, 2.5mmol), Stir at room temperature for 12 hours, dilute with ethyl acetate (30ml), wash three times with water, wash twice with saturated brine, dry over anhydrous sodium sulfate, filter, concentrate (the crude product can be directly used in the next reaction), column chromatography (petroleum ether: acetic acid Ethyl ester=2:1), a white powdery solid (1.07g, 90%) was obtained. ESI-MS m / z: 563.3[M+H] + , 585.3[M+ Na] + , 601.4[M+K] +

Embodiment 2

[0060] 3-Hydroxy-23-tert-butyldimethylsilyloxy-lupin-20(29)-en-28-oic acid benzyl ester

[0061] 3,23-Dihydroxy-lupine-20(29)-en-28-oic acid benzyl ester (1.00g, 1.8mmol) was dissolved in dichloromethane (30ml), and 4-dimethylaminopyridine (0.3 g, 2.5mmol) and tert-butyldimethylsilyl chloride (0.36g, 2.4mmol), stirred at room temperature for 4 hours, evaporated dichloromethane, diluted with ethyl acetate, washed with 10% hydrochloric acid until acidic, and washed with saturated brine until medium properties, dried over anhydrous sodium sulfate, filtered, concentrated (the crude solid can be directly used in the next reaction), column chromatography (petroleum ether: ethyl acetate = 20:1), and a white solid (1.11g, 92%) was obtained. 1 H-NMR (CDCl 3 , 300MHz): δ0.06(6H, s, Si-(CH 3 ) 2 ), 0.75, 0.84, 0.93, 1.67 (6H for 0.84, each 3H for others, s, 24, 25, 26, 27 and 30-CH 3 ), 0.90(9H, s, t-Bu), 2.13-2.20(1H, m), 2.25-2.28(1H, m), 3.01(1H, m, H-19), 3.33, 3.65(each1H, d, J...

Embodiment 3

[0063] 3-Carbonyl-23-tert-butyldimethylsilyloxy-lupine-20(29)-en-28-oic acid benzyl ester

[0064] 3-Hydroxy-23-tert-butyldimethylsilyloxy-lupine-20(29)-en-28-oic acid benzyl ester (1.03g, 1.5mmol) was dissolved in dichloromethane (30ml) and added Pyridine chlorochromate (0.5g, 2.3mmol), stirred at room temperature for 3 hours, evaporated dichloromethane, diluted with ethyl acetate, washed with water, washed with saturated brine, dried over anhydrous sodium sulfate, filtered, concentrated, column chromatography (petroleum ether : ethyl acetate=30:1), a white solid (0.91g, 89%) was obtained, mp151-154°C. 1 H-NMR (CDCl 3 , 300MHz): δ0.07(6H, s, Si-(CH 3 ) 2 ), 0.80, 0.83, 0.86, 0.96, 1.68 (each3H, s, 24, 25, 26, 27and30-CH 3 ), 0.87 (9H, s, t-Bu), 1.97 (3H, s, Ac), 2.18-2.32 (2H, m), 2.37-2.42 (2H, m), 3.04 (1H, m, H-19) , 3.28, 3.56 (each1H, d, J=9.1Hz, H-23), 4.61, 4.73 (each1H, d, J=1.2Hz, H-29), 5.09, 5.16 (each1H, d, J=12.2Hz, CH 2 -Ar), 7.35-7.38 (5H, m, H-Ar); ESI-...

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Abstract

The invention relates to the field of medicinal chemistry, particularly to a 23-hydroxy betulinic acid derivative. The invention further discloses a preparation method of the 23-hydroxy betulinic acid derivative as well as application of the compound of 23-hydroxy betulinic acid derivative and the medicinal composition thereof in 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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Patent Type & Authority Patents(China)
IPC IPC(8): C07J63/00A61K31/7024A61K31/56A61K31/58A61P35/00A61P35/02
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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