Dihydrochalcone derivates and use thereof

A technology of dihydrochalcones and derivatives, which is applied in the field of medicine and can solve problems that have not been seen before

Inactive Publication Date: 2009-07-22
SECOND MILITARY MEDICAL UNIV OF THE PEOPLES LIBERATION ARMY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

So far, there is no literature report about chalcone derivatives having blood lipid-lowering activity and hepatoprotective effect, and the drugs of such compounds in the treatment and prevention of diseases such as hyperlipidemia, fatty liver, liver cirrhosis and atherosclerosis middle application
[0004] In addition, in the compound of general formula I of the present invention, when R1 is benzyloxy, R2, R3, R4, R5, R8, R9, R11, R12 are H, R6 is a carbonyl group connected by a double bond, R7 is acetyl Oxygen group, R10 is the compound of methoxyl group has document (Bognar, R. The reactions of 2'-bnezyloxy-4-methoxychalcone epoxy, Acta Chimica Academiaa Scientiarum Hungariae, Tomus 1967, 67 (1), 83~92) report Its synthetic method, but there is no report about its activity

Method used

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  • Dihydrochalcone derivates and use thereof
  • Dihydrochalcone derivates and use thereof
  • Dihydrochalcone derivates and use thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0047] Example 1: Preparation of 3-(2-(benzyloxy)phenyl)-2-hydroxyl-1-(4-methoxyphenyl)-3-oxo-propanol acetate (DHC1)

[0048]

[0049] Using anisaldehyde and o-hydroxyacetophenone as starting materials, 2'-benzyloxy-4-methoxy Chalcones, then prepare DHC1 as follows:

[0050] 1) Preparation of 4-methoxy-2'-benzyloxychalcone epoxide

[0051] Take 3.4g of 4-methoxy-2'-benzyloxychalcone, add 50ml of acetone, 50ml of methanol, mix well and add 10ml of 2N NaOH at room temperature, 15ml of H 2 o 2 , stirred and reacted for 24 hours, then added 300ml of water to the reaction liquid, filtered, and the solid was recrystallized with acetone to obtain 3.2 g of white solid, with a yield of 89%.

[0052] 2) Preparation of 3-(2-(benzyloxy)phenyl)-2-hydroxyl-1-(4-methoxyphenyl)-3-oxo-propanol acetate (DHC1)

[0053] Take 500 mg of 4-methoxy-2'-benzyloxychalcone epoxide, add it into 10 ml of acetic acid, and stir the reaction at room temperature for 1 hour. Then, 100ml of water was ad...

Embodiment 2

[0056] Example 2: 3-(2-(Benzyloxy)phenyl)-2-hydroxy-1-(3,4-methylenedioxyphenyl)-3-oxo-propanol acetate (DHC2) preparation of

[0057]

[0058] Except that taking piperonal and o-hydroxyacetophenone as raw materials, all the other are the same as in Example 1. White crystals, melting point 157-161°C, yield 60%.

[0059] 1 HNMR (CDCl 3 )δ, ppm: 1.93 (3H, s, -CH 3 ); 4.01(1H, s, -OH); 5.18~5.28(2H, q, -CH2-); 5.36(1H, s, CH); 5.92(2H, s, -CH 2 -); 6.05~6.06(1H, d, CH); 6.48~6.52(1H, m, Ar-H); 6.59~6.61(1H, d.Ar-H); 6.68~6.69(1H, d.Ar- H); 7.10~7.14(2H, m, Ar-H); 7.39~7.47(6H, m, Ar-H); 7.54~7.60(1H, m, Ar-H), 7.80~7.83(1H, q, Ar-H)

[0060] MS(ESI)M+Na + =457.43

Embodiment 3

[0061] Example 3: Preparation of 1-(2-(benzyloxy)phenyl)-2,3-dihydroxy-3-(4-methoxyphenyl)acetone (DHC3)

[0062]

[0063] The preparation method of 4-methoxy-2'-benzyloxychalcone and 4-methoxyl-2'-benzyloxychalcone epoxide is the same as that of Example 1.

[0064] Take 100 mg of 4-methoxy-2'-benzyloxychalcone epoxide, add it to 10 ml of 15% NaOH solution, stir and react at room temperature for 3 hours, then pour the reaction solution into 50 ml of water, precipitate the solid and filter, Recrystallize from isopropanol to obtain a white solid with a melting point of 136-139°C.

[0065] 1 HNMR (CDCl 3 )δ, ppm: 3.77 (3H, s, -OCH 3 ); 3.78 (1H, d, -OH); 4.64 (1H, d, CH); 5.20~5.22 (2H, m, -OCH 2 -); 5.25(1H, s, CH); 6.75~6.78(2H, dd, Ar-H); 7.03~7.06(2H, dd, Ar-H); 7.09~7.14(2H, m, Ar-H) ;7.27~7.48(6H, m, Ar-H); 7.79~7.82(1H, m, Ar-H).

[0066] MS(ESI)M + =379.23

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Abstract

The invention relates to the technical field of medicines. Chalcone is a natural component in plants and has antibiotic and antifungal effects, and derivatives of the chalcone also have the effect of resisting tumors and the like. At present, no document is reported that the derivatives of the chalcone have the effect of reducing activity of blood fat and protecting the liver. The invention provides derivatives of the dihydrochalcone having a general formula I. Through tests of reducing blood fat, the results show that the derivatives of the dihydrochalcone have the effects of obviously reducing serum total cholesterol and low-density lipoprotein cholesterol, and can be used to prepare medicines or health products for reducing blood fat, preventing and treating hyperlipoidemia, fatty liver, hepatocirrhosis and atherosclerosis and protecting the liver.

Description

technical field [0001] The invention relates to the technical field of medicine, and relates to a class of dihydrochalcone derivatives and the application thereof in the preparation of medicines or health care products for preventing and treating hyperlipidemia, atherosclerosis and protecting the liver. Background technique [0002] Hyperlipidemia is a common cardiovascular disease, mainly caused by disorders of blood lipid metabolism, clinically divided into primary hyperlipidemia and secondary hyperlipidemia, often manifested as hypercholesterolemia (increased TC), hypertriglyceridemia (increased TG), or both. It is closely related to the occurrence and development of arteriosclerosis and cardiovascular diseases. Vascular diseases caused by abnormal blood lipids, such as high low-density lipoprotein cholesterol, high triglyceride, especially low high-density lipoprotein cholesterol, such as peripheral vascular disease, coronary heart disease, stroke disease, vascular rest...

Claims

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Application Information

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IPC IPC(8): A61K31/222A61K31/122A61K31/36A61K31/09C07C69/16C07C69/28C07C69/21C07D317/54C07C49/84C07C43/23A61P3/06A61P1/16A61P9/10A23L1/30A23L33/105
Inventor 金永生姜远英李林鹏刘广泉
Owner SECOND MILITARY MEDICAL UNIV OF THE PEOPLES LIBERATION ARMY
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