Synthesis and antimicrobial screening of 5-(benzylidene)-3-phenylthiazolidin-4-one derivatives incorporating thiazole ri
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Med Chem Res DOI 10.1007/s00044-013-0512-9
ORIGINAL RESEARCH
Synthesis and antimicrobial screening of 5-(benzylidene)-3phenylthiazolidin-4-one derivatives incorporating thiazole ring N. C. Desai • K. M. Rajpara • V. V. Joshi
Received: 26 August 2012 / Accepted: 24 January 2013 Ó Springer Science+Business Media New York 2013
Abstract The present article deals with the synthesis and antimicrobial screening of a series of N-(5-(2-(5-(arylidene)-4-oxo-3-phenylthiazolidin-2-ylidene)hydrazinecarbonyl)-4-methylthiazol-2-yl)-4-methoxybenzamides (6a–o). The structures of these compounds have been elucidated by spectra (IR, 1H NMR, 13C NMR, mass spectra). All the synthesized compounds were screened for in vitro antibacterial activity against Gram-positive (Staphylococcus aureus, Streptococcus pyogenes) and Gram-negative (Escherichia coli, Pseudomonas aeruginosa) bacteria. These compounds were also tested for their inhibitory action against three strains of fungi (Candida albicans, Aspergillus niger, Aspergillus clavatus). The thiazole derivatives discovered in this study may provide valuable therapeutic intervention for the treatment of microbial diseases, especially against bacterial and fungal infections. Keywords Antibacterial activity Antifungal activity MIC Thiazole Thiazolidinone
Introduction The search for new antimicrobial drugs is an area characterized by active investigation with the goal of overcoming the phenomenon of multiple drug resistance. Azoles constitute immensely important members of the aromatic heterocycle family due to their presence in a myriad of bioactive
N. C. Desai (&) K. M. Rajpara V. V. Joshi Division of Medicinal Chemistry, Department of Chemistry (DST-FIST Sponsored Department), Mahatma Gandhi Campus, Maharaja Krishnakumarsinhji Bhavnagar University, Bhavnagar 364 002, India e-mail: [email protected]
natural products as privileged pharmacophores. The thiazolyl group is also of great importance as it appears frequently in the structures of various natural products and biologically active compounds like thiamine (vitamin-B) and also in some antibiotic drugs like penicillin and micrococcin (Oncu et al., 2004). Several thiazole-containing drugs are available such as; nizatidine is a histamine H2-receptor antagonist that inhibits stomach acid production, and commonly used in the treatment of peptic ulcer disease (PUD) and gastroesophageal reflux disease (GERD), nitazoxanide as antiprotozal, sulfathiazole as antibiotic and abafungin as antifungal. The thiazolidinone nucleus also appears frequently in the structure of various natural products, notably thiamine, compounds possessing cardiac and glycemic benefits such as troglitazone (Ghazzi et al., 1997) and many metabolic products of fungi and primitive marine animals, including 2-(aminoalkyl)-thiazole-4-carboxylic acids (Ulrich et al., 1987). Numerous thiazolidinone derivatives have shown significant bioactivities such as antidiarrhoeal (Diurno et al., 1997), anticonvulsant (Ragab et al., 1997), antimicrobial (Sattigeri et
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