Synthesis of some 5,6-diaryl-1,2,4-triazine derivatives and investigation of their cyclooxygenase (COX) inhibitory activity

Abstract

Within this study, 20 2-[(5,6-diaryl-1,2,4-triazin-3-yl)thio]-N-(benzo/thiazol-2-yl)acetamide derivatives (4a-4t) were synthesized and COX inhibitory activities of the compounds were investigated. Compounds 4k-4o, which have a 4-methoxyphenyl group within their structures, showed strong inhibitory activity on COX-2 enzyme, even compound 4k, namely 2-{[5,6-bis(4-methoxyphenyl)-1,2,4-triazin-3-yl]thio}-N-(thiazol-2-yl)acetamide exhibited higher selectivity on this enzyme (IC₅₀:3.06 µM). Molecular docking studies were performed for compound 4k on COX-1 and COX-2 enzymes and the results were found to support the molecule’s COX-2 selectivity.

Graphical Abstract

Keywords:

• 1,2,4-Triazine
• diaryl heterocylics
• thiazole
• cyclooxygenase inhibition
• COX-2 inhibitor
• anti-inflammatory
• molecular docking

Acknowledgment

This study was supported by the Anadolu University Scientific Research Project, Eskisehir, Turkey (Project no. 1805S113).

Disclosure statement

The authors report no conflict of interests.