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Indolone-containing 4-thiazolidone derivatives and application thereof

A kind of technology of thiazolidinone and derivatives, applied in the field of medicine

Inactive Publication Date: 2014-04-09
SHENYANG PHARMA UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] 4-thiazolidinone derivatives containing indolinone belong to a new class of compounds, and there is no report on this compound and its related activities in the prior art

Method used

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  • Indolone-containing 4-thiazolidone derivatives and application thereof
  • Indolone-containing 4-thiazolidone derivatives and application thereof
  • Indolone-containing 4-thiazolidone derivatives and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0111] Add 8.8g (0.1mol) of N,N-dimethylethylenediamine into 200mL of anhydrous diethyl ether, then add dropwise a solution of 7.6g (0.1mol) of carbon disulfide in diethyl ether (50mL), continue stirring for 30min after dropping, and filter with suction. After washing with ether and drying, the solid was added to the reactor, followed by adding 200 mL of water and 50 mL of methanol. Add the pre-prepared potassium carbonate chloroacetic acid aqueous solution (potassium carbonate 6.9g (0.05mol), chloroacetic acid 9.4g (0.1mol), water 40mL) dropwise to the suspension, after dropping, react at 30°C for 7-8h, The insoluble matter was filtered off, and then 11 mL of concentrated sulfuric acid was added dropwise to the reaction solution. After the drop was completed, the reaction was carried out at 30° C. for 10 h. After the reaction was completed, the reaction solution was evaporated to dryness, 100 ml of ethanol was added to the residual liquid, the temperature was raised to reflux...

Embodiment 2

[0122] Example 3: 3-{5-(4-hydroxyphenylmethine)-3-[2-(dimethylamino)ethyl]-4-thiazolidinone-2-ylidene}-5-methanol yl-2-indolinone

[0123] MS (ESI) m / z: 422.5 (M+H) + ; 1 H NMR (300 MHz, DMSO- d6 ) δ : 2.04(s , 6H), 2.17 (s, 6H), 2.32 (s, 3H), 2.40-2.46(m, 7H), 4.37 (t, 2H), 4.86 (t, 2H), 6.82-7.78 (m , 16H), 10.35 (s, 2H) 10.55 (s, 1H), 10.75(s, 1H).

Embodiment 3

[0124] Example 4: 3-{5-(3,4-difluorophenylmethyl)-3-[2-(dimethylamino)ethyl]-4-thiazolidinone-2-ylidene}- 5-fluoro-2-indolinone

[0125] MS (ESI) m / z:446.4 (M+H) + ; 1 H NMR (300 MHz, DMSO- d6 ) δ : 2.05(s ,6H), 2.08(s, 6H), 2.39-2.49(m, 4H), 4.33(t, 2H), 4.86(t, 2H), 6.83-6.91(m, 2H), 7.01-7.07 (m, 2H), 7.42-7.94 (m, 10H ), 10.71 (s, 1H), 10.92(s, 1H).

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Abstract

The invention relates to indolone-containing 4-thiazolidone derivatives shown in a general formula I as well as geometrical isomers and pharmaceutically acceptable salts of the indolone-containing 4-thiazolidone derivatives. In the formula I, substituted groups namely Ar, R2, R3, R4 and n are defined in the specification. The invention also relates to application of compounds of the general formula I in preparation of a medicine for treating and / or preventing cancer.

Description

technical field [0001] The invention belongs to the technical field of medicine, and relates to new 4-thiazolidinone derivatives containing indolinone and pharmaceutically acceptable salts thereof, including their preparation methods and pharmaceutical compositions containing the compounds. The present invention also relates to the use of the derivative in the preparation of medicines for treating and / or preventing cancer. Background technique [0002] Compounds containing 4-thiazolidinone structure have a wide range of biological activities, such as antibacterial, antifungal, antiviral, anti-inflammatory, hypoglycemic, cardiotonic, and antitumor effects. J.K.Choi et al. reported 5-substituted phenylmethine rhodanine derivatives with PRL-3 inhibitory effect, and the compound IC with the best in vitro activity of this series of compounds 50 0.9 μM. N.S.Cutshall et al. reported a class of N-substituted phenyl-5-substituted phenylmethine rhodanine derivatives, which have inhi...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D417/04C07D417/14A61K31/427A61K31/454A61K31/5377A61P35/00A61P3/10A61P31/10A61P31/04A61P31/12A61P29/00A61P35/02
Inventor 宫平赵燕芳刘亚婧翟鑫
Owner SHENYANG PHARMA UNIVERSITY