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Dammarane triterpene derivative, pharmaceutical composition thereof, and applications of dammarane triterpene derivative in pharmacy

A technology for dammarane-type triterpenes and derivatives, which is applied in the field of dammarane triterpenoid derivatives and can solve problems such as no dammarane-type triterpenoids.

Active Publication Date: 2014-04-09
KUNMING INST OF BOTANY - CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

So far, there are no reports of dammarane-type triterpenoids as 11β-HSD1 inhibitors in the prior art

Method used

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  • Dammarane triterpene derivative, pharmaceutical composition thereof, and applications of dammarane triterpene derivative in pharmacy
  • Dammarane triterpene derivative, pharmaceutical composition thereof, and applications of dammarane triterpene derivative in pharmacy
  • Dammarane triterpene derivative, pharmaceutical composition thereof, and applications of dammarane triterpene derivative in pharmacy

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0051] The compound dammarane-type triterpene derivatives of the present invention have obvious 11β-HSD1 inhibitory activity, and the experimental methods and results are as follows:

[0052] 1. Materials and methods:

[0053] 1. Sample and preparation:

[0054] The sample was colorless, and was dissolved in dimethyl sulfoxide (DMSO) to prepare a stock solution with a concentration of 10 mg / ml and stored in the dark for future use.

[0055] 2. Biological model 11β-HSD1:

[0056] Human 11β-HSD1; mouse 11β-HSD1.

[0057] 3. Experimental method:

[0058] (1) Using the SPA (Scintillation proximity assay, liquid scintillation proximity assay technology) method, all derivatives were screened for the inhibition of mouse 11β-HSD1 and human 11β-HSD1, and 1 μM was selected as the initial screening concentration. Derivatives with an inhibition rate of more than 50% in the initial screening were re-screened, and the dose-effect relationship study was carried out, and the IC50 value ...

Embodiment 2

[0068] Preparation of Compound 8:

[0069]

[0070]

[0071] Dissolve 20 g of 20(s)-protopanaxadiol (compound 7) in 450 ml of methanol, add an appropriate amount of Raney Ni, connect a hydrogen balloon, pump three times to remove the air in the system, stir at room temperature overnight, and filter with diatomaceous earth , the filtrate was collected, and the solvent was distilled off under reduced pressure to obtain compound 13 as a white solid. ESI: 485 [M+23] + , 1 H-NMR ( CDCl 3 , 500MHz) characteristic signal δ: 3.51-3.61 (1H, td, J=5.2 / 10.3 / 10.3, H-C(12)), 3.17-3.21 (1H, dd, J=4.9 / 11.2, H-C(3)), 1.99 -2.06 (1H, td, J=7.1 / 10.6 / 10.6, H-C(13)).

[0072] Dissolve 5.7 g of compound 13 in 120 ml of dichloromethane, add 10.27 ml of triethylamine at 0 o Stir for 10min at C, 0 o Slowly add 4.66ml Ac 2 80 ml of dichloromethane solution of O, stirred at room temperature for 4 h after dropping, washed 3 times with saturated NaCl solution, and washed the organic phase w...

Embodiment 3

[0074] Preparation of compounds 1 and 2:

[0075]

[0076]

[0077] Dissolve 15 g of compound 8 in 150 ml of pyridine, 0 o Slowly add 4 eq POCl dropwise at C 3 50 ml of pyridine solution, 40 o Stirred at C for 8h, diluted with ethyl acetate, and washed with saturated CuSO 4 The solution was washed 3 times, and the organic phase was washed with anhydrous NaSO 4 After drying, the solvent was distilled off under reduced pressure to obtain Compound 14 as a pale yellow solid. ESI: 551 [M+23] + , 1 H-NMR ( CDCl 3 , 500MHz) characteristic signal δ: 5.03-5.06 (1H, t, J=6.6, H-C(22)) 4.89-4.96 (1H, td, J=5.3 / 10.9 / 10.9, H-C(12)), 4.45-4.49 ( 1H, dd, J=4.7 / 11.2, H-C(3)), 2.44-2.57 (1H, m, H-C(17)).

[0078] Dissolve 4 g of compound 14 in 40 ml of CCl 4 , add 60 ml saturated NaHCO 3 solution with 8.09 g NaIO 4 , stirred for 15 minutes, added 0.198 g RuCl 3 ·nH 2 O in MeCN solution 40 ml, the above mixture was stirred at room temperature for 4 days in the dark, filtered...

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PUM

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Abstract

The invention discloses a dammarane triterpene derivative represented by formula (I); a pharmaceutical salt thereof; a preparation method of the dammarane triterpene derivative; a pharmaceutical composition containing the dammarane triterpene derivative as an active ingredient; applications of the dammarane triterpene derivative, the pharmaceutical salt, and the pharmaceutical composition in preparation of medicines used for treating or preventing obesity, diabetes, hypertension, cardiovascular and cerebrovascular diseases, and related metabolic diseases; and applications of the dammarane triterpene derivative, the pharmaceutical salt, and the pharmaceutical composition in preparation of 11<beta>-HSD1 inhibitor.

Description

Technical field: [0001] The invention belongs to the technical field of medicines, in particular, it relates to dammarane triterpene derivatives, its preparation method and its pharmaceutical composition in the preparation, treatment or prevention of obesity, diabetes, hypertension, cardiovascular and cerebrovascular diseases and related metabolic diseases application in medicine. Background technique: [0002] Obesity and its related metabolic diseases (including type 2 diabetes, dyslipidemia, hypertension and cardiovascular complications, etc.) have become the main health problems plaguing modern people. According to incomplete statistics from the World Health Organization (WHO), there are about 1.6 billion overweight people in the world, of which 400 million people show clinical symptoms of diabetes, and the situation is still deteriorating. Although multiple targets have been found to be associated with metabolic syndrome, such as peroxi-some proliferators activated rec...

Claims

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Application Information

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IPC IPC(8): C07J7/00C07J9/00C07J1/00C07J13/00C07J71/00C07J5/00C07J11/00C07J75/00A61K31/57A61K31/575A61K31/568A61K31/56A61K31/5685A61K31/58A61K31/573A61P3/04A61P3/10A61P3/06A61P9/12A61P9/00A61P25/18A61P25/28A61P5/00
CPCY02P20/55
Inventor 赵勤实夏成峰冷颖邵立东
Owner KUNMING INST OF BOTANY - CHINESE ACAD OF SCI
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