Tanshinone derivatives, medicine compositions thereof, and purposes thereof in medicine

A technology of tanshinone and derivatives, applied in the field of tanshinone compounds, can solve the problems of no application and the like

Inactive Publication Date: 2012-07-25
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

Yet about the synthetic preparation patent of tanshinone derivative less (as: Qin Yinlin, Yan Peiling, He Longqi, the application of tanshinone IIA in pharmacy, publication number CN 1631364; Qin Yinlin, tanshinone I derivative and its application in pharmacy Publication No. CN 1837200; Du Zhiyun, Zhang Kun, Fang Yanxiong, Gu Lianquan, Huang Baohua, Zhao Suqing, Zhou Lihua, Zheng Jie, Tanshinone Derivatives and Their Application in the Preparation of Aldose Reductase Inhibitor Drugs, Publication No. CN 101012270; Gu Lianquan, Liu Peiqing, Li Guihua, Tanshinone IIA is used to prepare drugs for the prevention and treatment of atherosclerosis, publication number CN 1426782, etc.), and its activity is mainly concentrated in the traditional cardiovascular and tumor fields
At present, there is no synthesis and report about tanshinone derivatives in the prior art, nor does it serve as a selective 11-beta-HSD1 inhibitor and its use in the preparation and treatment of diabetes and related metabolic diseases (hypertension, obesity, senile dementia) etc.) reports on the application in medicine

Method used

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  • Tanshinone derivatives, medicine compositions thereof, and purposes thereof in medicine
  • Tanshinone derivatives, medicine compositions thereof, and purposes thereof in medicine
  • Tanshinone derivatives, medicine compositions thereof, and purposes thereof in medicine

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Experimental program
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Effect test

Embodiment 1

[0052] The specific experimental method of the present invention is as follows: using tanshinone IIA and cryptotanshinone separated from traditional Chinese medicine Danshen as starting materials, synthesizing tanshinone derivatives represented by general formula (I). Specifically, tanshinone IIA and cryptotanshinone are starting materials for the preparation of such compounds, and tanshinone IIA (T1) and cryptotanshinone (T2) can be isolated from the ethanol extract of traditional Chinese medicine Danshen.

[0053] The structural formulas of tanshinone IIA and cryptotanshinone are:

[0054]

[0055] The tanshinone compound shown in general formula (I) can be obtained through 1-4 step reaction by tanshinone IIA and cryptotanshinone through the reaction scheme among the embodiment 1 (see reaction scheme, figure 2 , 3 , 4).

[0056] figure 2 It is a reaction flow diagram for compounds derived from tanshinone IIA and cryptotanshinone A ring and B ring; reagents and reacti...

Embodiment 2

[0063] Preparation of compounds T3, T4, T5:

[0064]

[0065] To the CCl of compound T1 (29 mg, 0.1 mmol) 4 (5mL) solution, add NBS (27mg, 0.15mmol) and benzoyl peroxide (36mg, 0.15mmol) successively. After the addition, take a breath (N 2 ), and then reacted for 3 hours at room temperature. After the reaction is complete, add DCM to dilute, then use saturated Na 2 SO 3 Wash with aqueous solution, extract the aqueous phase with DCM three times (5mL×3), combine the organic phases, wash with saturated aqueous sodium chloride, dry over anhydrous sodium sulfate and concentrate, then column chromatography (petroleum ether:ethyl acetate=15:1), Compound T3 (15 mg, 50%) was obtained. The structural analysis data of compound T3 are as follows:

[0066] ESI-MS was measured on a shimadzu LCMS-2010EV mass spectrometer; 1D and 2D NMR were measured on a BrukerAM-300 and DRX-500 nuclear magnetic resonance instrument, the deuterated reagent used was produced by Sigma Aldrich, TMS was...

Embodiment 3

[0070] Preparation of Compound T6:

[0071]

[0072] To a solution of compound T3 (18 mg, 0.05 mmol) in DMF (1.0 mL), NaOAc (16 mg, 0.2 mmol) and TBAI (3 mg) were added sequentially. After the addition, the reaction was carried out at room temperature for 12 hours. After completion of the reaction, dilute with water (10 mL), then extract three times with EtOAc (8 mL × 3), combine the organic phases, wash with water and saturated aqueous sodium chloride successively, dry over anhydrous sodium sulfate, concentrate and column chromatography (petroleum ether: Ethyl acetate=6:1) to obtain compound T6 (12 mg, 70%).

[0073] Compound T6:: red solid, 1 H-NMR (500MHz, CDCl 3 )δ7.73(d, J=10Hz, 1H), 7.72(s, 1H), 6.41(s, 1H), 2.21(s, 3H), 2.02(s, 3H), 1.90-1.98(m, 2H) , 1.60(m, 4H), 1.40(s, 3H), 1.28(s, 3H);

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Abstract

The invention relates to tanshinone derivatives represented by a general formula (I), wherein the tanshinone derivatives are substituted by different groups on A ring, B ring, C ring, and D ring. The invention also relates to medicine compositions with the derivatives as active components, preparation methods of the medicines, and applications thereof in preparing a 1-type 11beta-hydroxysteroid dehydrogenase (11beta-HSD1) inhibiting agent. The invention also provides applications of the compounds represented by the general formula (I) in preparations of medicines used for treating diabetes and related metabolic diseases (such as hypertension, obesity, senile dementia, and the like).

Description

Technical field: [0001] The invention belongs to the technical field of pharmaceutical compounds and medicines, and in particular relates to a class of tanshinone compounds, which are pharmaceutical compositions of active ingredients, their preparation methods and the preparation of type 1 11-β-hydroxylation compounds and their pharmaceutical compositions. Steroid dehydrogenase (11β-HSD1) selective inhibitors neutralize the application of anti-diabetic and related metabolic (hypertension, obesity, senile dementia, etc.) drugs. Background technique: [0002] Diabetes and glucocorticoid-related metabolic diseases (including obesity, dyslipidemia, hypertension and cardiovascular complications, etc.) have become the main health problems that plague modern people (Rosenstock, J.et.Diabetes Care 2010, 33, 1516 .). 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 sho...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07J73/00C07C225/32A61K31/58A61K31/136A61P3/04A61P3/10A61P9/12A61P25/28
Inventor 赵勤实冷颖邓旭赵昱沈瑜罗晓星
Owner KUNMING INST OF BOTANY - CHINESE ACAD OF SCI
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