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Acrylamide compounds and medicinal uses thereof

A technology of acrylamide and compounds, which is applied in the field of acrylamide compounds and their medical applications, and can solve the problems of low selectivity and targeting

Active Publication Date: 2011-11-16
GENERAL HOSPITAL OF PLA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] However, the types and quantities of drugs for anti-apoptosis and cell protection available for clinical application are still very small, and their selectivity and targeting are not high. Cellular drugs, especially those with a new mechanism of action, are of great significance

Method used

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  • Acrylamide compounds and medicinal uses thereof
  • Acrylamide compounds and medicinal uses thereof
  • Acrylamide compounds and medicinal uses thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0072] Example 1 (2E)-3-(2-Thienyl)-N-[1-(8-quinolylamino)thioformylamino-2,2,2-trichloroethyl]-2-acrylamide

[0073]

[0074]Dissolve 1.12g of 2-thiophenecarbaldehyde and 3.12g of malonic acid in 15ml of pyridine, add a catalytic amount of piperidine, react at 80°C for 6 hours, pour the reaction solution into 20ml of water, adjust the pH to 12 with 10% NaOH aqueous solution, and extract with ethyl acetate. The aqueous layer was adjusted to pH 3 with 2N hydrochloric acid, and a large amount of yellow solid (2E)-3-(2-thienyl)acrylic acid was precipitated, which was filtered and washed with water to obtain 1.12 g. Dissolve (2E)-3-(2-thienyl)acrylic acid in 10ml of anhydrous dichloromethane, add a catalytic amount of DMF, add 1.5ml of oxalyl chloride dropwise in an ice-water bath, warm up to room temperature and stir for 2 hours after dropping, the reaction solution Drop into 10ml of concentrated ammonia water at 0°C, stir for 30min, separate the dichloromethane layer and eva...

Embodiment 2

[0075] Example 2 (2E)-3-(3-Thienyl)-N-[1-(8-quinolylamino)thioformylamino-2,2,2-trichloroethyl]-2-acrylamide

[0076]

[0077] Using the method of Example 1, the 2-thiophenecarbaldehyde was changed to 3-thiophenecarbaldehyde to obtain 0.60 g of a yellow solid. 1 H-NMR (400MHz, DMSO-d 6 )δ6.67-6.71(d, 1H); δ7.35-7.36(d, 1H); δ7.54-7.72(m, 6H); δ7.87-7.88(d, 1H); δ8.42-8.44 (dd, 1H); δ 8.96-9.03 (m, 3H); δ 9.54-9.56 (d, 1H); δ 11.05 (s, 1H). MS (TOF) 487.0 (M+).

Embodiment 3

[0078] Example 3 (2E)-3-(2-Thienyl)-N-[1-(4-methylphenylamino)thioformylamino-2,2,2-trichloroethyl]-2-acrylamide

[0079]

[0080] Using the method of Example 1, the 8-aminoquinoline was changed to 4-methylaniline to obtain 60 mg of yellow solid. 1 H-NMR (400MHz, DMSO-d 6 )δ2.28(s, 3H); δ6.47-6.51(d, 1H); δ7.13-7.18(m, 3H); δ7.36-7.45(m, 4H); δ7.66-7.72(m , 2H); δ8.03(, 1H); δ8.96-8.98(d, 1H); δ10.21(s, 1H). MS (TOF) 450.0 (M+).

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Abstract

The invention relates to compounds of the general formula I, or their isomers, medicinal salts and solvates. The invention also relates to compositions containing the compounds shown of the general formula I, or their isomers, medicinal salts and solvates, and pharmaceutically acceptable carriers, excipients or diluents. The invention further relates to uses of the compounds shown of the general formula I, or their isomers, medicinal salts and solvates in resisting cell apoptosis and preventing or treating of diseases or symptoms related to cell apoptosis, and especially in protecting cardiac muscle cells and preventing or treating diseases or symptoms related to cardiac muscle cell apoptosis.

Description

technical field [0001] The present invention relates to the field of medicinal chemistry, specifically, the present invention relates to acrylamide compounds and pharmaceutical compositions thereof, and the present invention also relates to said compounds and pharmaceutical compositions thereof for anti-apoptosis, prevention or treatment related to apoptosis The use for diseases or symptoms of cardiomyocytes, and the use for protecting cardiomyocytes and preventing or treating diseases or symptoms related to cardiomyocyte apoptosis. Background technique [0002] Apoptosis generally refers to a kind of programmed cell death that occurs during the development of cells in the body or under the action of certain factors through the regulation of intracellular genes and their products. Apoptosis is ubiquitous in the biological world, and occurs in both physiological and pathological conditions. It plays an important role in embryonic development and morphogenesis, the stability ...

Claims

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Application Information

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IPC IPC(8): C07D409/12C07D333/24C07D295/215C07C335/12A61K31/4709A61K31/381A61K31/5377A61K31/496A61K31/5375A61K31/4453A61K31/17A61P9/00A61P43/00
Inventor 何昆仑李松钟武刘涓王莉莉李鑫胡国梁王捷龙隆肖军海郑志兵李薇李蕊君刘春蕾
Owner GENERAL HOSPITAL OF PLA
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