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Novel applications of chalcone compound

A technology of chalcones and compounds, applied in the field of medicine, can solve problems such as lack, lack of triglyceride regulation, hypoglycemia, etc.

Inactive Publication Date: 2016-11-30
INST OF MATERIA MEDICA AN INST OF THE CHINESE ACAD OF MEDICAL SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

These drugs are only aimed at the index of hyperglycemia, but lack the regulation of triglycerides at the same time, and many antidiabetic drugs have a wide range of adverse reactions, such as liver toxicity, lactic acidosis, vitamin B 12 Deficiency and severe hypoglycemia etc.

Method used

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  • Novel applications of chalcone compound
  • Novel applications of chalcone compound
  • Novel applications of chalcone compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] Example 1 Preparation of 2-methoxyl-3'-hydroxyl-chalcone a

[0032]

[0033]Dissolve 3'-hydroxyacetophenone in absolute ethanol (10mg / mL), add 2-methoxybenzaldehyde (1eq.), and slowly add 40% KOH aqueous solution dropwise under stirring at 0°C, and stir overnight at room temperature. The remaining raw materials were extracted with ether, the aqueous layer was acidified with 2M hydrochloric acid, the solid precipitated out, extracted with ethyl acetate, dried and concentrated over anhydrous sodium sulfate, and recrystallized from ethanol to obtain 2-methoxy-3′-hydroxy-chalcone a (yellow solid, 84%). And NMR and mass spectrometry were performed on a, the results are as follows: 1 HNMR (300MHz, CDCl 3 )δ: 8.12(d, J=15.9Hz, 1H), 7.62(t, J=6.3Hz, 1H), 7.59(d, J=15.9Hz, 1H), 7.55(m, 2H), 7.35-7.41( m,2H),7.07(dd,J 1 =7.8Hz,J 2 =2.1Hz,1H),6.91-7.02(m,2H),3.92(s,3H).ESI-MS:[M+H]+:255.1.

Embodiment 2

[0034] Example 2 Preparation of 4-methoxy-2′,6′-dihydroxy-chalcone b

[0035]

[0036] (1). Dissolve 2′,6′-dihydroxyacetophenone (350 mg, 2.30 mmol) in 20 mL of anhydrous dichloromethane, and add N,N-diisopropylethylamine ( 0.76 mL, 4.60 mmol) and chloromethyl methyl ether (0.26 mL, 3.45 mmol), stirred for 4.5h. Add 20 mL of ethyl acetate, and wash with saturated sodium bicarbonate solution, 30 mL of water and 30 mL of saturated brine successively. The organic layer was dried over anhydrous sodium sulfate, concentrated, and column chromatography (petroleum ether / ethyl acetate=20:1~15:1) gave 2′-hydroxyl-6′-methoxymethyleneoxyacetophenone ( Colorless oily liquid, 440 mg, yield 97.8%).

[0037] (2). 2'-hydroxy-6'-methoxymethyleneoxyacetophenone (200 mg, 1.02mmol) and 4-methoxybenzaldehyde (153mg, 1.12mmol) were dissolved in 10mL of ethanol, After cooling to 0°C, 10 mL of 40% potassium hydroxide aqueous solution was added dropwise. After stirring at room temperature for 18...

Embodiment 3

[0039] Example 3 The preparation of 2-methoxy-2', 3'-dihydroxy-chalcone c:

[0040]

[0041] In Example 2 (1), 2', 6'-dihydroxyacetophenone is replaced with 2', 3'-dihydroxyacetophenone, and 2'-hydroxyl-3'-methoxyl group is obtained in (1) Methyleneoxyacetophenone (colorless oily liquid, 380mg, yield 84.5%); 2'-hydroxyl-3'-methoxymethyleneoxyacetophenone and 2-methoxybenzaldehyde were used for (2) react to get 2-methoxy-2'-hydroxyl-3'-methoxymethyleneoxy-chalcone (yellow solid, 250 mg, 78.0%); Methyl protection gave the product 2-methoxy-2',3'-dihydroxy-chalcone c (yellow solid, 110 mg, 91.2%). And c was characterized by NMR and mass spectrometry, the results are as follows: 1 HNMR (Acetone-d6) δ: 13.20(s, 1H), 8.33(d, J=15.6Hz, 1H), 8.03(d, J=15.6Hz, 1H), 7.94-7.92(m, 2H), 7.73( d, J=8.4Hz, 1H), 7.48(t, J=7.8Hz, 1H), 7.15(d, J=8.0Hz, 2H), 7.04(t, J=7.4Hz, 1H), 6.87(t, J=7.8Hz,1H),3.99(s,3H). 13 CNMR(Acetone-d6)δ:195.5,160.0,152.7,147.3,141.3,133.5,130.0,124.1,121.8,12...

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Abstract

The invention relates to applications of a chalcone compound in preparation of farnesoid X receptor (FXR) antagonist drugs, and specifically relates to applications of a multi-hydroxy (multi-methoxy) substituted chalcone compound represented by formula I or a pharmaceutically acceptable salt thereof in preparation of farnesoid X receptor (FXR) antagonists and drugs used for preventing and treating diabetes mellitus type 2. The chalcone compound possesses antagonistic action on CDCA (chenodeoxycholic acid and FXR endogenous ligands)-induced farnesoid X receptor activation, is capable of reducing blood glucose and triglyceride of mice, and possesses application potentialities in treating diabetes mellitus type 2.

Description

technical field [0001] The invention relates to a class of polyhydroxy polyalkoxy substituted chalcones and pharmaceutically acceptable salts thereof as FXR antagonists for the preparation of new drugs for preventing and treating type 2 diabetes and hyperlipidemia, belonging to the technical field of medicine. Background technique [0002] Diabetes is one of the most common chronic diseases that seriously endanger human health. With the advancement of science and technology and the change of people's lifestyle, the incidence rate is increasing year by year. According to the Baker Heart and Diabetes Institute in Australia, the global incidence of diabetes will reach 7.7% by 2030, and a total of 439 million people will suffer from diabetes; from 2010 to 2030, the incidence of diabetes among adults in developing countries will increase by 69%. The incidence of diabetes among adults in developed countries will increase by 20%. 【See: Shaw J E, Sicree R A, Zimmet P Z. Globalesti...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A61K31/12A61P3/06A61P3/10
CPCA61K31/12
Inventor 方唯硕申竹芳张国宁贾春明
Owner INST OF MATERIA MEDICA AN INST OF THE CHINESE ACAD OF MEDICAL SCI
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