Design and synthesis of novel heterocyclic acetamide derivatives for potential analgesic, anti-inflammatory, and antimicrobial activities

Abstract

A new series of heterocyclic amides were synthesized by the reaction of heterocyclic amines with substituted phenylacetic acids 1 in the presence of EDC.HCl as a coupling agent. The newly synthesized compounds were characterized by IR, NMR, mass spectral, and elemental analysis. All the synthesized compounds were evaluated for their in vivo analgesic, anti-inflammatory, and in vitro antimicrobial activities. Among the tested acetamides, the compounds 2a, 3b, 4d, 4e, and 4f showed potential anti-inflammatory and analgesic activities. The compounds which exhibited good anti-inflammatory activity were docked to mouse COX-1 (PDB ID: 2CZT) and COX-2 (PDB ID: 3LN1) enzymes to predict their putative interactions. The compound 2-(2-Bromophenyl)-N-(pyrazin-2-yl)acetamide (4f) emerged as most potent molecule with synergistic anti-inflammatory, analgesic, and antimicrobial properties.