Substituent activity relationship studies on new azolo benzoxazepinyl oxazolidinones

Abstract In an effort to discover potent antibacterials based on the entropically favored ‘bioactive conformation’ approach, a series of novel tricyclic molecules mimicking the conformationally constrained structure of Linezolid is reported. Based on the initial tricyclic molecule 1 , the benzazepine derivative 2 was designed where the tricyclic structure had more flexibility around C–N bond compared to 1 . While, the molecule 2 was less active, the molecule 3 showed promising antibacterial activity presumably after having obtained rigidity due to pyrrole ring. The syntheses, SAR studies, and evaluation of 3 as a lead compound are reported.