Novel 2,4-dichlorophenoxy acetic acid substituted thiazolidin-4-ones as anti-inflammatory agents: Design, synthesis and biological screening

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• 作者：Yakub Ali^a ; Mohammad Sarwar Alam^a ; ^{msalam@jamiahamdard.ac.in} ; ^{msalam5555@gmail.com} ; Hinna Hamid^a ; ^{hhamid@jamiahamdard.ac.in} ; Asif Husain^b ; Abhijeet Dhulap^c ; Sameena Bano^a ; Chetna Kharbanda^a
• 关键词：2-Imino-4-thiazolidinone ; Anti-inflammatory ; COX-2 ; TNF-α ; Anti-nociceptive ; Ulcerogenic
• 刊名：Bioorganic & Medicinal Chemistry Letters
• 出版年：2017
• 出版时间：15 February 2017
• 年：2017
• 卷：27
• 期：4
• 页码：1017-1025
• 全文大小：2556 K
• 卷排序：27

文摘

A library of fourteen 2-imino-4-thiazolidinone derivatives (1a-1n) has been synthesized and evaluated for in vivo anti-inflammatory activity and effect on ex-vivo COX-2 and TNF–α expression. Compounds 1k (5-(2,4-dichloro-phenooxy)-acetic acid (3-benzyl-4-oxo-thiazolidin-2-ylidene)-hydrazide) and 1m (5-(2,4-dichloro-phenooxy)-acetic acid (3-cyclohexyl-4-oxo-thiazolidin-2-ylidene)-hydrazide) exhibited in vivo inhibition of 81.14% and 78.80% respectively after 5 h in comparison to indomethacin which showed 76.36% inhibition of inflammation without causing any damage to the stomach. Compound 1k showed a reduction of 68.32% in the level of COX-2 as compared to the indomethacin which exhibited 66.23% inhibition of COX-2. The selectivity index of compound 1k was found to be 29.00 in comparison to indomethacin showing selectivity index of 0.476. Compounds 1k and 1m were also found to significantly suppress TNF-α concentration to 70.10% and 68.43% in comparison to indomethacin which exhibited 66.45% suppression.