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Synthesis, characterization, COX1/2 inhibition and molecular modeling studies on novel 2-thio-diarylimidazoles. | LitMetric
Heterocyclic compounds with diaryl substituents have been a milestone approach for selective cyclooxygenase 2 (COX 2) inhibition by bioisosteric replacements and modifications. It is also known that thiazole derivatives have different pharmacological activities. In this study, nine novel 2-[(1,5-diphenyl-1-imidazole-2-yl)thio]-N-(thiazole-2-yl)acetamide derivatives (Compound ) were synthesized via the reaction of 1,5-disubstitued phenyl-imidazole-2-thiole and -thiazole acetamide. The inhibitory effects of COX-1 and COX-2 enzymes were tested for the synthesized compounds. Enzyme-ligand interactions of the most active compound on COX subtypes were elucidated by molecular modeling studies. The percent inhibitory effect for compound , which is the naked derivative among all the compounds, was found to be the most active on COX-2 at 10 μM concentration (: 88%, SC-560: 98.2%, : 60.9%); whereas compound showed the highest inhibitory effect and was found to be the most selective derivative on COX-1 isoenzyme (: 85%, DuP-697: 97.2%, : 57.9%).
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