Novel 2, 4-dichlorophenoxy acetic acid substituted thiazolidin-4-ones as anti-inflammatory agents: Design, synthesis and biological screening. Issue 4 (15th February 2017)

• Record Type: Journal Article
• Authors: Ali, Yakub; Alam, Mohammad Sarwar; Hamid, Hinna; Husain, Asif; Dhulap, Abhijeet; Bano, Sameena; Kharbanda, Chetna
• Is Part Of: Bioorganic & medicinal chemistry letters. Volume 27:Issue 4(2017)
• Page Start: 1017
• Page End: 1025
• Publication Date: 2017-02-15
• Subjects: 2-Imino-4-thiazolidinone -- Anti-inflammatory -- COX-2 -- TNF-α -- Anti-nociceptive -- Ulcerogenic; Bioorganic chemistry -- Periodicals; Pharmaceutical chemistry -- Periodicals; 572
• DOI: 10.1016/j.bmcl.2016.12.069
• Languages: English
• ISSNs: 0960-894X

Abstract

Graphical abstract: Abstract: 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. Compounds1k (5-(2, 4-dichloro-phenooxy)-acetic acid (3-benzyl-4-oxo-thiazolidin-2-ylidene)-hydrazide) and1m (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. Compound1k 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 compound1k was found to be 29.00 in comparison to indomethacin showing selectivity index of 0.476. Compounds1k and1m were also found to significantly suppress TNF-α concentration to 70.10% and 68.43% in comparison to indomethacin which exhibited 66.45% suppression.