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

Ertaş M., Biltekin S. N., Berk B., YURTTAŞ L., Demirayak Ş.

Phosphorus, Sulfur and Silicon and the Related Elements, vol.197, no.11, pp.1123-1135, 2022 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Review
  • Volume: 197 Issue: 11
  • Publication Date: 2022
  • Doi Number: 10.1080/10426507.2022.2062756
  • Journal Name: Phosphorus, Sulfur and Silicon and the Related Elements
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Academic Search Premier, Chemical Abstracts Core
  • Page Numbers: pp.1123-1135
  • Keywords: 1, 2, 4-Triazine, diaryl heterocylics, thiazole, cyclooxygenase inhibition, COX-2 inhibitor, anti-inflammatory, molecular docking
  • Istanbul Medipol University Affiliated: Yes

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.