Use of pentacylic triterpene compounds in preparing glycogenic phosphorylase inhibitor

A technology of glycogen phosphorylase and pentacyclic triterpenoids, which is applied in drug combinations, medical preparations containing active ingredients, and pharmaceutical formulas, etc.

Inactive Publication Date: 2005-10-19
CHINA PHARM UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

So far, the inventors have not seen any report that pentacycli

Method used

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  • Use of pentacylic triterpene compounds in preparing glycogenic phosphorylase inhibitor
  • Use of pentacylic triterpene compounds in preparing glycogenic phosphorylase inhibitor
  • Use of pentacylic triterpene compounds in preparing glycogenic phosphorylase inhibitor

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Experimental program
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preparation example Construction

[0032] Preparation of pentacyclic triterpenoids:

[0033] Reagents and test methods: Infrared spectrum was measured with NieoletImpact 410 IR spectrometer, and KBr pellets were used; 1HNMR and 13CNMR were measured with ACF-300(500) BRUK nuclear magnetic resonance; MS was measured with HP1100 mass spectrometer. Ursolic acid (purity about 95%) was purchased from Shaanxi Huike Plant Development Co., Ltd.; oleanolic acid (purity about 97%) was purchased from Chengdu Super Human Phytochemical Development Co., Ltd.; white birch bark was collected from Inner Mongolia; other reagents and solvents All commercially available chemically pure or analytically pure products were used directly without treatment unless otherwise specified.

Embodiment 1

[0034] Embodiment 1: the preparation of maslinic acid and its benzyl ester

[0035] Oleanolic acid (10.0g) was suspended in 100mL of anhydrous DMF, heated at 100°C to dissolve completely, and then added K 2 CO 3 (6.04g) and benzyl chloride (3.0mL). The mixture was heated at 100°C with stirring until the starting material disappeared (ca. 3 hours). After cooling, filter with suction, and wash the solid with DMF 3 times, 15 mL each time. Pour the mother liquor into 500mL of water, shake while pouring to disperse the precipitated solids, let stand until the solids are completely precipitated, collect the solids by suction filtration, and wash them thoroughly with water. After drying, 11.51 g of white crude benzyl oleanate was obtained (crude yield 96%). The crude product can be directly used in the next reaction. 1 HNMR (CDCl 3 , 500MHz): δ0.62, 0.78, 0.88, 0.90, 0.92, 0.98, 1.13(each, 3H, s), 2.91(1H, dd, J=4.4, 13.9Hz, H-18), 3.20(1H, dd , J=4.5, 11.2Hz, H-3α), 5.07 (2H,...

Embodiment 2

[0040] Embodiment 2: the preparation of benzyl ursolic acid, corosolic acid and benzyl ester thereof

[0041] Suspend ursolic acid (10.0g) in 100mL of anhydrous DMF, heat at 100°C to dissolve completely, let stand for a little cooling, then add K 2 CO 3 (6.04g) and benzyl chloride (3.0mL). The mixture was heated at 100°C with stirring until the starting material disappeared (ca. 3 hours). After cooling, filter with suction, and wash the solid with DMF 3 times, 15 mL each time. Pour the mother liquor into 500mL of water, shake while pouring to disperse the precipitated solids, let stand until the solids are completely precipitated, collect the solids by suction filtration, and wash them thoroughly with water. After drying, 11.54 g of white benzyl ursolic acid crude product was obtained (crude yield 96.4%). 1 HNMR (CDCl 3 , 300MHz): δ0.67, 0.81, 0.92, 0.97, 1.01, 1.10(each, 3H, s), 0.88(3H, d, J=6.4Hz), 2.30(1H, d, J=11.3Hz, H- 18), 3.24 (1H, dd, J=4.6, 10.8Hz, H-3α), 5.09...

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Abstract

The present invention relates to application of pentacyclic triterpene compounds in preparing glycogenic phosphorylase inhibitor, and includes the application of medicine composition of crataegolic acid, Corosolic acid, oleanolic acid, ursolic acid, betulin, betulic acid, lupeol or their pharmaceutically acceptable salt or ester in preparing medicine for treating diabetes.

Description

technical field [0001] The invention relates to the application of pentacyclic triterpenoids in the preparation of glycogen phosphorylase inhibitors, including the application in the preparation of antidiabetic drugs. Background technique [0002] Glycogen is the storage form of sugar in the body, mainly found in the muscles and liver. Muscle glycogen degradation can provide energy for muscle contraction, while liver glycogen degradation mainly maintains blood sugar concentration. [0003] The degradation of glycogen involves glycogen phosphorylase. The enzyme catalyzes the phosphorylation of glycogen, and the resulting glucose-1-phosphate is converted into glucose-6-phosphate under the catalysis of phosphoglucomutase, which either enters the glycolysis reaction or is converted into glucose-6-phosphate Glucose is generated under the catalysis of enzymes, enters the blood, and provides glucose for other tissues. Since glycogen phosphorylase is a very important factor in en...

Claims

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Application Information

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IPC IPC(8): A61K31/56A61P3/10A61P9/10A61P35/00
Inventor 孙宏斌温小安柳军张陆勇王善治倪沛洲
Owner CHINA PHARM UNIV
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