Antimicrobial activity of thiazolyl benzenesulfonamide-condensed 2,4-thiazolidinediones derivatives
- 829 Downloads
A new series of benzoyl chloride-substituted 2,4-thiazolidinedione derivatives have been synthesized by the condensation of 2-amino-4-aryl-thiazole and 4′-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 2,4-thiazolidinedione 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.
KeywordsThiazole 2,4-Thiazolidinedione Synthesis Antibacterial Antituberculosis
The authors are thankful to the Department of Chemistry, Narmada College of Commerce and Science, Bharuch for providing research facility. The authors are also thankful to Prof. Dr. Bhaskar M. Rawal and Nikhil M. Parekh for their help during the research work.
- Aneja DK, Lohan P, Arora S, Sharma C, Aneja KR, Prakash Om (2011) Synthesis of new pyrazolyl-2,4-thiazolidinediones as antibacterial and antifungal agents. Org Med Chem Lett 15:1–11Google Scholar
- Barreca ML, Chimirri A, De Luca L, Monforte AM, Monforte P, Rao A, Zappala` M, Balzarini J, De Clercq E, Pannecouque C, Witvrouw M (2001) Discovery of 2,3-diaryl-1,3-thiazolidin-4-ones as potent anti-HIV-1 agents. Bioorg Med Chem Lett 11:1793–1796. doi: 10.1016/S0960-894X(01)00304-3 PubMedCrossRefGoogle Scholar
- Geronikaki AA, Lagunin AA, Hadjipablou-Litina DI, Eleftheriou ET, Filimonov DA, Poroikov VV, Alam I, Saxena AA (2008) Computer-aided discovery of anti-inflammatory thiazolidinones with dual cyclooxygenase/lipoxygenase inhibition. J Med Chem 51:1601–1609. doi: 10.1021/jm701496h PubMedCrossRefGoogle Scholar
- Knutsen LJS, Hobbs CJ, Earnshaw CG, Fiumana A, Gilbert J, Mellor SL, Radford F, Ward SDC, James IF (2007) Synthesis and SAR of novel 2-arylthiazolidinones as selective analgesic N-type calcium channel blockers. Bioorg Med Chem Lett 17:662–667. doi: 10.1016/j.bmcl.2006.10.098 PubMedCrossRefGoogle Scholar
- Madhukar A, Kannapan N, Deep A, Kumar P, Kumar M, Verma P (2009) Synthesis and antimicrobial studies of biphenyl-4-carboxylic acid 5-(arylidine)2-(aryl)-4-oxothiazolidin-3yl amides. Int J Chem Tech Res 1:1376–1380Google Scholar
- Malik S, Upadhyaya P, Miglani S (2011) Thiazolidinediones: a plethro of biological load. Int J Pharmtech Res 3(1):62–75Google Scholar
- Ottana R, Maccari R, Barreca ML, Bruno G, Rotondo A, Rossi A, Chiricosta G, Paola R, Sautebin DL, Cuzzocre S, Vigorit MG (2005) 5-Arylidene-2-imino-4-thiazolidinones: design and synthesis of novel anti-inflammatory agents. Bioorg Med Chem 13:4243–4252. doi: 10.1016/j.bmc.2005.04.058 PubMedCrossRefGoogle Scholar
- Rekha S, Shantharam U, Chandy V (2011) Synthesis and evaluation of novel thiazolidinediones for anti inflammatory activity. Int Res J Pharm 2(9):81–84Google Scholar
- Shiradkar MR, Ghodake M, Bothara KG, Bhandari SV, Nikalje A, Akula KC, Desai NC, Burangeb PJ (2007) Synthesis and anticonvulsant activity of clubbed thiazolidinone–barbituric acid and thiazolidinone–triazole derivatives. Arkivoc (xiv): 58–74Google Scholar
- Srivastav T, Gaikwad AK, Haq W, Sinha S, Katti SB (2005) Synthesis and biological evaluation of 4-thiazolidinone derivatives as potential antimycobacterial agents. Arkivok (ii):120–130Google Scholar