5-benzylidene-2,4-thiazolidinedione derivatives and preparation method and application thereof

A technology for the reaction of thiazolidinedione and thiazolidinedione, which is applied in the field of chemical medicine

Inactive Publication Date: 2011-02-16
SICHUAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] In summary, there is no application of 2,4-thiazolidinedione derivatives in the treatment of acute hepatitis, rheumatoid arthritis, systemic lupus erythematosus, pulmonary fibrosis and other immune diseases.

Method used

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  • 5-benzylidene-2,4-thiazolidinedione derivatives and preparation method and application thereof
  • 5-benzylidene-2,4-thiazolidinedione derivatives and preparation method and application thereof
  • 5-benzylidene-2,4-thiazolidinedione derivatives and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0045] The preparation of embodiment 1 (Z)-2-(4-((2,4-thiazoldione-5-methylene) methyl) phenoxy group)-N-benzene-acetamide

[0046]

[0047] Step 1: Synthesis of 2-chloro-N-benzene-acetamide

[0048]Under ice-bath stirring, aniline (1.86g, 20mmol) and triethylamine (24mmol, 3.3ml) were dissolved in anhydrous dichloromethane (20ml), then chloroacetyl chloride (2.71g, 24mmol) was slowly added dropwise into the above solution. The mixture was stirred at room temperature for 12 hours. Then the solvent was removed under reduced pressure, the obtained solid was washed with ice water (100ml), filtered, and finally the crude product was recrystallized with diethyl ether / petroleum ether mixed solvent to obtain 3.1 g of white solid (yield 92%).

[0049] 1 H NMR (400MHz, CDCl 3 )δ8.232 (s, 1H), 7.562-7.540 (m, 2H), 7.385-7.341 (m, 2H), 7.199-7.156 (m, 1H), 4.195 (s, 2H);

[0050] Mass Spectrum: 170.01[M+H] + .

[0051] Step 2: Synthesis of 2-(4-formylphenoxy)-N-benzene-acetamid...

Embodiment 2

[0059] The preparation of embodiment 2 (Z)-2-(4-((2,4-thiazoldione-5-methylene) methyl) phenoxy group)-N-p-toluene-acetamide

[0060]

[0061] Step 1: Synthesis of 2-chloro-N-p-methylphenylacetamide

[0062] Under stirring in an ice bath, p-methylaniline (2.14g, 20mmol) and triethylamine (24mmol, 3.3ml) were dissolved in anhydrous dichloromethane (20ml), then chloroacetyl chloride (2.71g, 24mmol) was slowly was added dropwise to the above solution. The mixture was stirred at room temperature for 12 hours. Then the solvent was removed under reduced pressure, the obtained solid was washed with ice water (100ml), filtered, and finally the crude product was recrystallized with diethyl ether / petroleum ether mixed solvent to obtain 3.65g of white solid (yield 99.3%).

[0063] NMR: (400MHz, CDCl 3 )δ8.192(s, 1H), 7.424(d, 2H, J=8.4Hz), 7.162(d, 2H, J=8.0Hz), 4.182(s, 2H), 2.334(s, 3H);

[0064] Mass Spectrum: 182.04[M+H] - .

[0065] Step 2: Synthesis of 2-(4-formylphenoxy)-...

Embodiment 3

[0073] The preparation of embodiment 3 (Z)-2-(4-((2,4-thiazolyldione-5-methylene) methyl) phenoxy group)-N-p-methoxybenzene-acetamide

[0074]

[0075] The preparation method is the same as in Example 1, and a light yellow solid (87.9% yield) is obtained, and the identification data are as follows:

[0076] NMR: (400MHz, DMSO-d 6 )δ12.535(s, 1H), 10.009(s, 1H), 7.761(s, 1H), 7.588(d, 2H, J=8.4Hz), 7.533(d, 2H, J=8.8Hz), 7.157( d, 2H, J=8.4Hz), 6.899(d, 2H, J=4.8Hz), 4.766(s, 2H), 3.724(s, 3H);

[0077] Mass Spectrum: 383.10[M+H] - .

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Abstract

The invention belongs to the field of chemical medicines, and in particular relates to 5-benzylidene-2,4-thiazolidinedione derivatives and a preparation method and application thereof. Aiming at solving the first technical problem, the invention provides a new series of 5-benzylidene-2,4-thiazolidinedione derivatives shown in a formula I, which has he function of treating immunologic diseases.

Description

technical field [0001] The invention belongs to the field of chemistry and medicine, and particularly relates to 5-benzylidene-2,4-thiazolidinedione derivatives and their preparation methods and uses. Background technique [0002] Currently marketed 2,4-thiazolidinedione (TZDs) drugs such as troglitazone (troglitazone), rosiglitazone (rosiglitazone), pioglitazone (pioglitazone), ciglitazone (ciglitazone) are mainly used for Treat diabetes. In recent years, studies have found that TZDs also have good medical value in the treatment of cardiovascular diseases, inhibition of psoriasis, and anti-tumor. [0003] Anti-atherosclerosis is the most prominent effect of TZDs on cardiovascular. The direct effects of TZDs anti-atherosclerosis include increasing the bioavailability of nitric oxide, reducing the interaction between leukocytes and endothelial cells, reducing the migration of vascular smooth muscle cells and Proliferation and cholesterol efflux from macrophages. [0004] T...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D417/12A61K31/4439C07D277/34A61P1/16A61P29/00A61P19/04A61P9/00A61K31/426A61P11/00A61P37/02A61P1/00A61P1/18
Inventor 陈俐娟魏于全罗有福向明礼
Owner SICHUAN UNIV
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