Synthesis of a new series of 2-(2-oxo-2 H -chromen-3-yl)-5 H -chromeno[4,3- b ]pyridin-5-ones by two facile methods and
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Med Chem Res (2013) 22:4745–4754 DOI 10.1007/s00044-013-0489-4
ORIGINAL RESEARCH
Synthesis of a new series of 2-(2-oxo-2H-chromen-3-yl)-5Hchromeno[4,3-b]pyridin-5-ones by two facile methods and evaluation of their antimicrobial activity Apoorva A. Patel • Hemali B. Lad • Kinnar R. Pandya • Chirag V. Patel Dinkar I. Brahmbhatt
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Received: 17 August 2012 / Accepted: 11 January 2013 / Published online: 22 January 2013 Ó Springer Science+Business Media New York 2013
Abstract A series of novel 2-(2-oxo-2H-chromen-3-yl)5H-chromeno[4,3-b]pyridin-5-ones 4a–4l have been synthesized using two methodologies (using Mannich base of 4-hydroxy coumarin and 4-chloro-3-formyl coumarin) (Patel et al., 2012) and assayed for their antibacterial activity against gram-positive bacteria viz. Bacillus subtilis (MTCC 441), Staphylococcus aureus (MTCC 96) and gram-negative bacteria viz. Escherichia coli (MTCC 443), Salmonella typhimurium (MTCC 98). The compounds 4a–4l were also assayed for their antifungal activity against Aspergillus niger (MTCC 282) and Candida albicans (MTCC 227). All the compounds 4a–4l exhibited potent inhibitory activity against gram-positive bacteria compared to standard drugs at the tested concentrations. The compounds also showed appreciable activity against gram-negative bacteria as well as fungi. The compounds 4e, 4f, 4i, 4k, and 4l are found to be the most proficient members of the series and emerged as potential molecules for further development. Keywords Krohnke’s reaction 3-[(Ethylamino)methyl]-4-hydroxy coumarin 4-Chloro-2-oxo-2H-chromene-3-carbaldehyde 1-[2-Oxo-2-(2-oxo-2H-chromen-3-yl)ethyl]pyridinium salt Antimicrobial activity
Apoorva A. Patel and Hemali B. Lad contributed equally to this study.
Electronic supplementary material The online version of this article (doi:10.1007/s00044-013-0489-4) contains supplementary material, which is available to authorized users. A. A. Patel H. B. Lad K. R. Pandya C. V. Patel D. I. Brahmbhatt (&) Department of Chemistry, Sardar Patel University, Vallabh Vidhyanagar 388120, Gujarat, India e-mail: [email protected]
Introduction The treatment of infectious diseases still remains an important and challenging problem because of a combination of factors including emerging infectious diseases and the increasing number of multi-drug resistant microbial pathogens with particular relevance for gram-positive bacteria (Tenover and McDonald, 2005; Pfeltz and Wilkinson, 2004; Roberts, 2004; Kratky et al., 2012; Muroi et al., 2004). On the other hand, a recent survey of novel small molecule therapeutics revealed that the majority of them result from an analog-based approach and that their market value represents two-thirds of all drug sales (Wermuth, 2006). 2H-Chromen2-ones (coumarins) are important oxygen containing heterocycles which possess variety of biological activities such as anti-inflammatory (Timonen et al., 2011), antibacterial (Song et al., 2012), antioxidant (Xiao et al., 2012), anticoagulant (Mladenovic et al., 2012), anti-HIV (Olmedo et al., 2
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