Synthesis, Antibacterial Activity and Molecular Docking Study of a Series of 1,3-Oxazole-Quinoxaline Amine Hybrids

Abstract

A series of 1,3-oxazole-quinoxaline amine hybrids were prepared successfully through a copper-free Sonogashira coupling followed by heteroannulation in a one-pot process. The reaction of benzoyl chlorides, prop-2-yn-1-amine, and 2-amine-substituted 3-chloroquinoxalines catalyzed by Pd(Ph₃P)₂Cl₂ in the presence of tris(benzyltriazolylmethyl)amine (TBTA) as an efficient ligand in EtOH produced 1,3-oxazole-quinoxaline amine hybrids in high yields. All synthesized 1,3-oxazole-quinoxaline amine hybrids were screened for antibacterial properties and were exposed to molecular docking studies. Molecular docking study manifested the possible binding mode of compounds with its bacterial target protein. The consequences of biological activity and docking study disclosed that the increase of lipophilic and extra hydrogen bond characters are essential for suitable antibacterial activity.

Graphical Abstract

Keywords:

• 1,3-oxazole
• quinoxaline
• Sonogashira coupling
• copper-free
• antibacterial activity
• molecular docking

Disclosure statement

No potential conflict of interest was reported by the author(s).