Synthesis of new imidazothiazole derivatives and investigation of their anti-inflammatory and analgesic activities

Autor: Soyer Can, Okşan, Ünlü, Serdar, Ocak, Hale, Çöldür, Elif Çisem, Sipahi, Hande, Bilgin Eran, Belkıs
Zdroj: Journal of the Iranian Chemical Society; February 2022, Vol. 19 Issue: 2 p579-587, 9p
Abstrakt: In this study, new carboxamides derived from the imidazo[2,1-b]thiazole skeleton which are carrying the biologically active benzoxazole group and are terminated with polar group such as chloro/bromo/cyano as well as imidazothiazole-based methyl carboxylate derivative were synthesized in order to investigate anti-inflammatory and analgesic activities. The new molecules were characterized by FT-IR, 1H-NMR, 13C-NMR and ESI–MS spectrometry. New chloro-terminated imidazothiazole-based carboxamide (7a) and imidazothiazole-based methyl carboxylate derivative (8) showed, respectively, 75.88% and 77.05% cell viability on RAW 264.7 cell line at dose of 1.5 μM and 50 μM whereas trifluoroacetylamino-substituted thiazole carboxylate (1), trifluoroacetylamino-substituted thiazole carboxamides (2) and amino-substituted thiazole carboxamides (3) exhibited non-cytotoxicity by the cell viability value which is higher than 80% at dose of 100 μM except for their brominated derivatives 2band 3bwith highest cytotoxicity. Anti-inflammatory assay of the compounds on RAW 267.7 cells revealed that the compounds N-(4-chlorophenyl)-2-[(trifluoroacetyl)amino]-1,3-thiazole-5-carboxamide (2a) and 2-amino-N-(4-chlorophenyl)-1,3-thiazole-5-carboxamide (3a) which are starting materials in the synthetic route of 7asignificantly have similar nitrite reducing effect with indomethacin which is positive control compound. As regarding to analgesic activity, compound 3ashowed the highest reducing activity on PGE2level induced by LPS than trifluoroacetylamino-substituted carboxamides 2aand 2bas compared with control group.
Databáze: Supplemental Index
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