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23-hydroxy betulinic acid derivative, preparation method, preparation and use thereof

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

Inactive Publication Date: 2008-07-30
CHINA PHARM UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0012] 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, preparation method, preparation and use thereof
  • 23-hydroxy betulinic acid derivative, preparation method, preparation and use thereof
  • 23-hydroxy betulinic acid derivative, preparation method, preparation and use thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0210] 3,23-O-Diacetyl betulinic acid (X3)

[0211] Dissolve 23-hydroxybetulinic acid (0.12g, 0.25mmol) in 5ml of pyridine in a 10ml eggplant-shaped flask, add acetic anhydride (0.15ml, 1.5mmol) dropwise, and stir overnight at room temperature. Dilute with 10ml of ethyl acetate, wash with 9% hydrochloric acid to pH 4-5, wash with saturated brine (5ml×3), dry over anhydrous magnesium sulfate, filter, and recrystallize from ethyl acetate to obtain 0.136g of light yellow powdery solid. The rate is 98%.

[0212]ESI-MS: 579[M+Na] +

[0213] 1 HNMR (300Hz, CDCl 3 ), δ (ppm): 0.80 (s, 3H, CH 3 ), 0.88 (s, 3H, CH 3 ), 0.93 (s, 3H, CH 3 ), 0.97 (s, 3H, CH 3 ), 1.69 (s, 3H, CH 3 ), 2.01 (s, 3H, CH 3 ), 2.06(s, 3H, CH 3 ), 3.00 (m, 1H, C 19 -H), 3.68~3.70(d, 1H, 23-H), 3.83~3.85(d, 1H, 23-H), 4.61(s, 1H, 29-H), 4.74(s, 1H, 29-H ), 4.75~4.78(m, 1H, 3-H)

Embodiment 2

[0215] 3,23-O-Diacetyl-28-betulinoyl chloride (BYA-2)

[0216] Dissolve 3,23-O-diacetyl-28-acid-betulinic acid (0.1g, 0.18mmol) in 5ml of refined and dried dichloromethane in a 10ml eggplant-shaped bottle, add 0.1ml of oxalyl chloride dropwise, and stir at room temperature for 4h , the dichloromethane was distilled off. Refined and dried dichloromethane (5ml×3) was added, dissolved and evaporated. Finally, 0.1 g of a light yellow glassy solid was obtained.

Embodiment 3

[0218] 3,23-Diacetyl-28-methyl betulinate (SZ1)

[0219] Dissolve BYA-2 (0.1 g, 0.17 mmol) prepared by the method in Example 2 in a 10 ml eggplant-shaped flask with 5 ml of refined and dried dichloromethane, add 5 ml of methanol dropwise, and stir at room temperature for 6 h. Wash with saturated brine (5ml×3), dry over anhydrous sodium sulfate, filter, and concentrate the filtrate to make sand. Column chromatography [petroleum ether (60°C-90°C): ethyl acetate = 12:1 (v:v)] gave 0.092 g of a white powdery solid, with a total yield of 90.0%, and mp 110-112°C.

[0220] ESI-MS: 593[M+Na] +

[0221] 1 HNMR (300Hz, CDCl 3 ), δ (ppm): 0.78 (s, 3H, CH 3 ), 0.83 (s, 3H, CH 3 ), 0.87 (s, 3H, CH 3 ), 0.89 (s, 3H, CH 3 ), 1.68 (s, 3H, CH 3 ), 1.99 (s, 3H, CH 3 ), 2.04(s, 3H, CH 3 ), 2.94~3.01 (m, 1H, C 19 -H), 3.64(s, 3H, CH 3 -O), 3.59~3.68(d, 1H, 23-H), 3.79~3.83(d, 1H, 23-H), 4.57(s, 1H, 29-H), 4.71(s, 1H, 29-H ), 4.71~4.77(m, 1H, 3-H)

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Abstract

The invention relates to modified 23-hydroxybetulinic acid derivative (1), which belongs to the natural medicine and pharmaceutical chemistry field. The definition of R1, R2, and R3 is shown in the instruction. The invention also discloses a preparation method of the 23-hydroxybetulinic acid derivative, the medicine composition containing the 23-hydroxybetulinic acid derivative, and the use thereof in tumor resistance.

Description

technical field [0001] The present invention relates to the field 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 of the compound and the use of such 23-hydroxy betulinic acid derivatives for anti-tumor. Background technique [0002] This application is a divisional application for the original application 200610040277.2. [0003] 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 bacill...

Claims

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Application Information

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IPC IPC(8): C07J63/00A61K31/56A61P35/00
Inventor 吴晓明徐进宜毕毅周金培张陆勇袁貹涛李丹徐萍
Owner CHINA PHARM UNIV
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