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Mol Divers. 2015 Nov;19(4):653-67. doi: 10.1007/s11030-015-9600-8. Epub 2015 Apr 28.

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.

Author information

1
Faculty of Technology & Engineering, Kalabhavan, The M. S. University of Baroda, Vadodara, 390001, Gujarat, India.
2
Faculty of Technology & Engineering, Kalabhavan, The M. S. University of Baroda, Vadodara, 390001, Gujarat, India. mryadav11@yahoo.co.in.

Abstract

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.

KEYWORDS:

3-Benzazepine; Anti-obesity agents; Phenethyl fragment; Regioselective alkylation; Selective agonists

PMID:
25916735
DOI:
10.1007/s11030-015-9600-8
[Indexed for MEDLINE]

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