Medicinal Chemistry Research

, Volume 22, Issue 6, pp 2737–2745 | Cite as

Antimicrobial activity of thiazolyl benzenesulfonamide-condensed 2,4-thiazolidinediones derivatives

  • Nikhil M. Parekh
  • Krunal V. Juddhawala
  • Bhaskar M. Rawal
Original Research


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.


Thiazole 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.


  1. Alegaon SG, Alagawadi KR (2011) New thiazolidinedione-5-acetic acid amide derivatives: synthesis, characterization and investigation of antimicrobial and cytotoxic properties. Med Chem Res. doi: 10.1007/s00044-011-9598-0 Google Scholar
  2. Amr A, Sabrry NM, Abdalla MM, Abdel BF (2009) Synthesis, antiarrhythmic and anticoagulant activities of novel thiazolo derivatives from methyl 2-(thiazol-2-ylcarbamoyl)acetate. Eur J Med Chem 44:25–735. doi: 10.1016/j.ejmech.2008.05.004 CrossRefGoogle Scholar
  3. 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
  4. 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
  5. Bhargava PN, Chaurasia MR (1969) New local anesthetics: derivatives of 5-diethylaminoacetamido-2-arylimino-3-aryl-4-thiazolidones. J Pharm Sci 58(7):896–898PubMedCrossRefGoogle Scholar
  6. Bondock S, Khalifa W, Fadda AA (2007) Synthesis and antimicrobial evaluation of some new thiazole, thiazolidinone and thiazoline derivatives starting from 1-chloro-3,4-dihydronaphthalene-2-carboxaldehyde. Eur J Med Chem 42:948–954. doi: 10.1016/j.ejmech.2006.12.025 PubMedCrossRefGoogle Scholar
  7. Chawla P, Singh R, Saraf SK (2011) Syntheses and evaluation of 2,5-disubstituted 4-thiazolidinone analogues as antimicrobial agents. Med Chem Res. doi: 10.1007/s00044-011-9730-1 Google Scholar
  8. Deep A, Jain S, Sharma PC, Phogat P, Malhotra M (2011) Synthesis of 2-(aryl)-5-(arylidene)-4-thiazolidinone derivatives with potential analgesic and anti-inflammatory activity. Med Chem Res. doi: 10.1007/s00044-011-9679-0 Google Scholar
  9. Desai NC, Dodiya AM, Makwana AH (2011a) Antimicrobial screening of novel synthesized benzimidazole nucleus containing 4-oxo-thiazolidine derivatives. Med Chem Res. doi: 10.1007/s00044-011-9752-8 Google Scholar
  10. Desai NC, Dodiya AM, Shihora PN (2011b) A clubbed quinazolinone and 4-thiazolidinone as potential antimicrobial agents. Med Chem Res. doi: 10.1007/s00044-011-9674-5 Google Scholar
  11. Fuloria NK, Singh V, Shaharyar M, Ali M (2009) Synthesis, characterization andantimicrobial evaluation of novel imines and thiazolidinones. Acta Pol Pharm 66:141–146PubMedGoogle Scholar
  12. 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
  13. 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
  14. Kucukguzel SG, Oruc EE, Rollas S, Sahin F, Ozbek A (2002) Synthesis, characterisation and biological activity of novel 4-thiazolidinones, 1,3,4-oxadiazoles and some related compounds. Eur J Med Chem 37:197–206. doi: 10.1016/S0223-5234(01)01326-5 PubMedCrossRefGoogle Scholar
  15. Kucukguzel G, Kocatepe AE, Clercg D, Sahin F, Gulluce M (2006) Synthesis and biological activity of 4-thiazolidinones, thiosemicarbazides derived from diflunisal hydrazide. Eur J Med Chem 41:353–359. doi: 10.1016/j.ejmech.2005.11.005 PubMedCrossRefGoogle Scholar
  16. Kumar A, Rajput CS (2009) Synthesis and anti-inflammatory activity of newer quinazolin-4-one derivatives. Eur J Med Chem 44:83–90. doi: 10.1016/j.ejmech.2008.03.018 PubMedCrossRefGoogle Scholar
  17. 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
  18. Malik S, Upadhyaya P, Miglani S (2011) Thiazolidinediones: a plethro of biological load. Int J Pharmtech Res 3(1):62–75Google Scholar
  19. 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
  20. Ozkirimli S, Kazan F, Tunali Y (2009) Synthesis, antibacterial and antifungal activities of 3-(1,2,4 triazole-3-yl)-4-thiazolidinones. J Enzyme Inhib Med Chem 24:447–452PubMedCrossRefGoogle Scholar
  21. Patel NB, Patel SD (2010) Synthesis and antimicrobial study of fluoroquinolonebased 4-thiazolidinones. Med Chem Res 19:757–770CrossRefGoogle Scholar
  22. Patel D, Kumari P, Patel N (2011) Synthesis of 3-{4-[4-dimethylamino-6-(4-methyl-2-oxo-2Hchromen-7-yloxy)-[1,3,5]triazin-2-ylamino]-phenyl}-2-phenyl-5-(4-pyridin-2-yl piperazin-1-ylmethyl)-thiazolidin-4-one and their biological evaluation. Med Chem Res. doi: 10.1007/s00044-011-9822-y Google Scholar
  23. 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
  24. 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
  25. 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
  26. Tandon M, Kumar P, Pande K, Bhalla TN, Barthwal JP (1985) Novel thiazolidinones as potent anti-inflammatory and analgesic agents. Pharmacology 31(5):260–267. doi: 10.1159/000138130 PubMedCrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media New York 2012

Authors and Affiliations

  • Nikhil M. Parekh
    • 1
  • Krunal V. Juddhawala
    • 2
  • Bhaskar M. Rawal
    • 2
  1. 1.Department of Applied ChemistryS. V. National Institute of TechnologySuratIndia
  2. 2.Department of ChemistryNarmada College of Science and CommerceZadeshwar, BharuchIndia

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