Regioselective alkylation of 1,3,4,5-tetrahydrobenzo[d]azepin-2-one and biological evaluation of the resulting alkylated products as potentially selective 5-HT2C agonists

The benzazepine ring system has offered interesting CNS-active medicinal agents. Taking this privileged structure as the basic scaffold, C 1 and/or N 3 -alkylated benzazepin-2-one derivatives and their reduced analogs have been prepared as potential 5-HT 2 C receptor agonists. The selective alkylation at the C 1 and/or N 3 positions of this seven-membered lactam ring is here reported for the first time under different reaction conditions. The synthesized compounds were evaluated for their biological profile as potential 5-HT 2 C agonists using a classic pharmacological approach. Three derivatives ( 15, 17, and 20 ) have shown promising 5-HT 2 C agonistic activity which can be further optimized as anti-obesity agents for the treatment of male sexual dysfunction. Further, a homology model for 5-HT 2 C receptor was generated using MODELLER, and ligand–receptor interactions for these potential molecules were studied.