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, [Formula: see text] and/or [Formula: see text]-alkylated benzazepin-2-one derivatives and their reduced analogs have been prepared as potential [Formula: see text] receptor agonists. The selective alkylation at the [Formula: see text] and/or [Formula: see text] 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 [Formula: see text] agonists using a classic pharmacological approach. Three derivatives (15, 17, and 20) have shown promising [Formula: see text] agonistic activity which can be further optimized as anti-obesity agents for the treatment of male sexual dysfunction. Further, a homology model for [Formula: see text] receptor was generated using MODELLER, and ligand-receptor interactions for these potential molecules were studied.
Faculty of Technology & Engineering, Kalabhavan, The M. S. University of Baroda, Vadodara, 390001, Gujarat, India.
Navnit
N
Prajapati
Faculty of Technology & Engineering, Kalabhavan, The M. S. University of Baroda, Vadodara, 390001, Gujarat, India.
Rajani
R
Giridhar
Faculty of Technology & Engineering, Kalabhavan, The M. S. University of Baroda, Vadodara, 390001, Gujarat, India.
Anshuman
A
Sinha
Faculty of Technology & Engineering, Kalabhavan, The M. S. University of Baroda, Vadodara, 390001, Gujarat, India.
Ashish M
AM
Kanhed
Faculty of Technology & Engineering, Kalabhavan, The M. S. University of Baroda, Vadodara, 390001, Gujarat, India. mryadav11@yahoo.co.in.
Mange Ram
MR
Yadav
D000818:Animals; D001552:Benzazepines / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D008297:Male; D008958:Models, Molecular; D015394:Molecular Structure; D010410:Penile Erection; D010413:Penis / Q000187:drug effects*; D051381:Rats; D017207:Rats, Sprague-Dawley; D012702:Serotonin Antagonists / Q000138:chemical synthesis* / Q000737:chemistry; D040681:Structural Homology, Protein
D001552:Benzazepines; D012702:Serotonin Antagonists
3-Benzazepine; Anti-obesity agents; Phenethyl fragment; Regioselective alkylation; Selective agonists