Synthesis and biological evaluation of 1-(3-chloro-2-oxo-4-phenylazetidin-1-yl)-3-(2-oxo-2-(10 H -phenothiazin-10-yl)eth
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Med Chem Res (2013) 22:2578–2588 DOI 10.1007/s00044-012-0255-z
ORIGINAL RESEARCH
Synthesis and biological evaluation of 1-(3-chloro-2-oxo-4phenylazetidin-1-yl)-3-(2-oxo-2-(10H-phenothiazin-10yl)ethyl)urea derivatives A. Rajasekaran • K. Sheeja Devi
Received: 27 February 2012 / Accepted: 21 September 2012 / Published online: 4 October 2012 Ó Springer Science+Business Media New York 2012
Abstract A new series of eleven novel 1-(3-chloro-2-oxo-4phenylazetidin-1yl)-3-(2-oxo-2-(10H-phenothiazin-10-yl)ethyl) urea derivatives were synthesized by cyclocondensation of various Schiff bases of phenothiazine with chloroacetyl chloride in the presence of triethylamine. Various Schiff bases of pheno thiazine were synthesized by condensation of 4-(2-oxo-2-(10H -phenothiazin-10-yl)ethyl semicarbazide with various aryl aldehydes. The synthesized compounds were characterized by IR, MASS and 1H NMR spectral data and evaluated for in vitro antimicrobial, antitubercular, antioxidant and anticancer activities by disc diffusion method, MIC method, REMA, DPPH, FRAP and MTT assay method, respectively. All synthesized compounds showed moderate-to-significant anti-bacterial and anti-fungal activity and compound 4d, 4g, 4h and 4k showed good antioxidant activity with EC50 value of 55, 57, 56 and 47 lg/ml tested by DPPH method. The compounds 4j at a concentration of 10 lg/ml showed inhibition against the growth of Mycobacterium tuberculosis and 4f showed significant activity against human cervical cancer cell line with IC50 values of 18.26 lM.
more popular as an area of research and provides a most valuable molecular template for the development of agents that are able to interact with a wide variety of biological processes. They have been shown to possess a broad spectrum of biological activities as antinociceptive (Gildasio et al., 2004), antimicrobial (Gautam et al., 2011; Wainwright et al., 2011; Radadiya et al., 2005), anti-tumour (Krsti et al., 2011; Plutal et al., 2010), antimalarial (Martha et al., 2002) and anti-tubercular (Aaron et al., 2007) agents. The cyclic 2-azetidinone skeleton has been extensively used as a template to build the heterocyclic structure fused to the fourmembered ring (Srivastava et al., 2010). The activity of the famous antibiotics such as penicillins, cephalosporins and carbapenems are attributed to the presence of 2-azetidinone ring in them. In continuation of our research in the synthesis of new congeners by incorporating phenothiazine and azetidinone moieties in a single molecular frame work (Rajasekaran et al., 2010), herein, we report the synthesis and biological evaluation of some new 1-(3-chloro-2-oxo-4-phenylazetidin-1-yl)3-(2-oxo-2-(10H-phenothiazin-10-yl)ethyl)urea derivatives.
Keywords Phenothiazines 2-Azetidinones MTT assay REMA Materials and methods Introduction The chemistry of nitrogen–sulphur heteroatom containing aromatic compounds particularly phenothiazine is becoming
A. Rajasekaran (&) K. S. Devi Department of Pharmaceutical Chemistry, KMCH College of Pharmacy, Kalapatti Road,
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