Antimicrobial activity of thiazolyl benzenesulfonamide-condensed 2,4-thiazolidinediones derivatives
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Med Chem Res DOI 10.1007/s00044-012-0273-x
ORIGINAL RESEARCH
Antimicrobial activity of thiazolyl benzenesulfonamide-condensed 2,4-thiazolidinediones derivatives Nikhil M. Parekh • Krunal V. Juddhawala Bhaskar M. Rawal
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Received: 6 April 2012 / Accepted: 6 October 2012 Ó Springer Science+Business Media New York 2012
Abstract A new series of benzoyl chloride-substituted 2,4-thiazolidinedione derivatives have been synthesized by the condensation of 2-amino-4-aryl-thiazole and 40 -chlorosulfonyl benzylidine-2,4-thiazolidinedione. New compounds were evaluated for their in vitro antibacterial activity against Staphylococcus aureus, Bacillus subtilis, Escherichia coli, and Pseudomonas aeruginosa. Furthermore, new products were tested for in vitro antituberculosis activity against Mycobacterium tuberculosis using isoniazid and rifampicin as control drugs. The results of bioassay demonstrated that some of the newly synthesized 2,4thiazolidinedione derivatives emerged as lead molecules with excellent MIC (mg/mL) values against mentioned organisms compared to standard drugs. The structure of the final analogs has been confirmed on the basis of IR, 1H NMR, mass spectral, and elemental analysis. Keywords Thiazole 2,4-Thiazolidinedione Synthesis Antibacterial Antituberculosis
Introduction Small-ring heterocycles holding nitrogen and sulfur have been under investigation for a long time because of their synthetic diversity and therapeutic relevance. Among the N. M. Parekh (&) Department of Applied Chemistry, S. V. National Institute of Technology, Surat 395 007, Gujarat, India e-mail: [email protected] K. V. Juddhawala B. M. Rawal Department of Chemistry, Narmada College of Science and Commerce, Zadeshwar, Bharuch 392 001, Gujarat, India e-mail: [email protected]
wide range of heterocycles explored to develop privileged candidates in drug discovery, thiazoles have been indentified to play an essential role in medicinal chemistry. Thiazolidinone are the derivatives of thiazolidine which belong to prenominal group of heterocyclic compounds bearing sulfur and nitrogen in a five-member ring (Patel et al., 2011; Desai et al., 2011a, b). Countless research work on thiazolidinones has been accomplished in recent years (Malik et al., 2011; Rekha et al., 2011; Aneja et al., 2011). The nucleus is also well known as wonder nucleus because it gives out different derivatives expressing newer leads for multiple biological activities (Chawla et al., 2011). Over the years, 4-thiazolidinones skeleton has been a fertile source of biopotent heterocycles possessing diverse chemotherapeutic activities (Bhargava and Chaurasia, 1969). In the recent past, 4-thiazolidinone scaffold and its derivatives have fascinated significant interest of medicinal chemists and have become an important class of heterocyclic compounds because of their utility for miscellaneous biological activities such as anti-inflammatory (Deep et al., 2011; Kumar and Rajput, 2009; Ottana et al., 2005; Geronikaki et al., 2008), analgesic (Tandon et al
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