Synthesis and structure-antibacterial activity relationship studies of 4-substituted phenyl-4,5-dihydrobenzo[f][1,4]oxazepin-3(2H)-thiones

Agirbas H., Kemal B., BUDAK F.

MEDICINAL CHEMISTRY RESEARCH, vol.20, no.8, pp.1170-1180, 2011 (Journal Indexed in SCI) identifier identifier

  • Publication Type: Article / Article
  • Volume: 20 Issue: 8
  • Publication Date: 2011
  • Doi Number: 10.1007/s00044-010-9457-4
  • Page Numbers: pp.1170-1180


The synthesis and characterization of a series of 4-substituted phenyl-4,5-dihydrobenzo[f][1,4]oxazepin-3(2H)-thiones were presented. Preliminary in vitro antimicrobial activity of the compounds was assessed against a panel of microorganisms including S. aureus, E. faecalis, P. aeruginosa, E. coli, and C. albicans. Some of the compounds exhibited significantly in vitro antimicrobial activity. The pMIC values were correlated with physicochemical descriptors: Hammett substituent constants (sigma (m) and sigma (p) ) and the lipophilic constant (pi). One statistical significant 2D-QSAR model was obtained with para-substituted compounds. The pMIC values were also correlated with some theoretical descriptors as independent variables and four statistical significant 2D-QSAR models were also obtained with meta-substituted compounds.