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

摘要

The benzazepine ring system has offered interesting CNS-active medicinal agents. Taking this privileged structure as the basic scaffold, and/or -alkylated benzazepin-2-one derivatives and their reduced analogs have been prepared as potential receptor agonists. The selective alkylation at the and/or 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 agonists using a classic pharmacological approach. Three derivatives (15, 17, and 20) have shown promising agonistic activity which can be further optimized as anti-obesity agents for the treatment of male sexual dysfunction. Further, a homology model for receptor was generated using MODELLER, and ligand-receptor interactions for these potential molecules were studied.