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Medicinal Chemistry Research

, Volume 21, Issue 8, pp 2064–2071 | Cite as

Syntheses and evaluation of 2,5-disubstituted 4-thiazolidinone analogues as antimicrobial agents

  • Pooja Chawla
  • Ranjit Singh
  • Shailendra K. SarafEmail author
Original Research

Abstract

Two novel series of 4-thiazolidinone derivatives, bearing 2-nitrophenyl imino and 4-nitrophenyl imino groups at position-2 and substituted arylidene groups at position-5, have been synthesized and evaluated for antimicrobial activity against four bacterial and one fungal strain. The success of the synthesis of compounds was confirmed on the basis of spectral analysis. All the newly synthesized compounds were obtained in high yields and exhibited good antibacterial activity; however, the antifungal potential was limited to a few agents.

Keywords

4-Thiazolidinones Arylidene Spectral analysis Antimicrobial 

Notes

Acknowledgments

The authors are thankful to Central Drug Research Institute, Lucknow, India for the library facility and spectral characterization.

References

  1. Indian Pharmacopoeia (1996) Biological Assay, Govt. of India, Delhi 2:A100–A102Google Scholar
  2. Bruno G, Costantino L, Curinga V, Maccari R, Monforte F, Nicolo F, Ottana R, Vigorita MG (2002) Synthesis and aldose reductase inhibitory activity of 5-arylidene-2,4-thiazolidinediones. Bioorg Med Chem. 10:1077–1084PubMedCrossRefGoogle Scholar
  3. Chavan AA, Rai NR (2007) Synthesis and antimicrobial screening of 5-arylidene-2-imino-4-thiazolidinones. Arkivoc xvi:148–155Google Scholar
  4. Choudhari BR, Shinde DB, Shingare MS (1995) Synthesis of some 2-imino-N-(6′- substituted benzothio-2′-yl)-4- thiazolidinones and  their bis derivatives as antibacterial agents. Asian J Chem. 7:832–836Google Scholar
  5. Chugh TD (2008) Emerging and re-emerging bacterial diseases in India. J Biosci 33:549–555PubMedCrossRefGoogle Scholar
  6. Geronikaki AA, Lagunin AA, Hadjipavlou-Litina DI, Eleftheriou PT, Filimonov DA, Poroikov VV, Alam I, Saxena AK (2008) Computer aided discovery of potential anti-inflammatory thiazolidinones with dual 5-LOX/COX inhibition. J Med Chem 51:1601–1609PubMedCrossRefGoogle Scholar
  7. Goel B, Ram T, Tyagi R, Bansal E, Kumar A, Mukherjee D, Sinha JN (1999) 2-Substituted-3-(4-bromo-2-carboxyphenyl)-5-methyl-4-thiazolidinones as potential anti-inflammatory agents. Eur J Med Chem 34:265–269CrossRefGoogle Scholar
  8. Ispida T, In Y, Inoue M, Tanaka C, Hamanaka N (1990) Conformation of (Z)-3-carboxymethyl-[(2E)-2-methyl-3-phenylpropenylidene]rhodanine (epalrestat), a potent aldose reductase inhibitor: X-ray crystallographic, energy calculational, and nuclear magnetic resonance studies. J Chem Soc Perkin Trans. 2:1085–1091Google Scholar
  9. Khan MW, Alam MJ, Rashid MA, Chowdhary R (2005) A new structural alternative in benzo[b]furans for antimicrobial activity. Bioorg Med Chem. 13:4796–4805CrossRefGoogle Scholar
  10. Kukukguzel G, 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 37:197–206CrossRefGoogle Scholar
  11. Liu H-L, Li Z, Anthonsen T (2000) Synthesis, characterisation and biological activity of novel 4-thiazolidinones, 1,3,4-oxadiazoles and some related compounds. Molecules 5:1055–1061CrossRefGoogle Scholar
  12. Mehta PD, Sengar NPS, Subrahmanyam EVS, Satyanarayana D (2006) Synthesis and biological activity studies of some thiazolidinones and azetidinones. Indian J Pharm Sci. 68:103–106CrossRefGoogle Scholar
  13. Momose Y, Meguro K, Ikeda H, Hatanaka C, Oi S, Sohda T (1991) Studies on antidiabetic agents. X. synthesis and biological activities of pioglitazone and related compounds. Chem Pharm Bull 39:1440–1445PubMedCrossRefGoogle Scholar
  14. Omar K, Geronikaki A, Zoumpoulakis P, Camoutsis C, Sokovic M, Ciric A, Glamoclija J (2010) Novel 4-thiazolidinone derivatives as potential antifungal and antibacterial drugs. Bioorg Med Chem. 18:426–432PubMedCrossRefGoogle Scholar
  15. Ottana R, Maccari R, Barreca ML, Bruno G, Rotondo A, Rossi A, Chiricosta G, Di Paola R, Sautebin L, Cuzzocrea SE, Vigorita MG (2005) 5-Arylidene-2-imino-4-thiazolidinones: design and synthesis of novel anti-inflammatory agents. Bioorg Med Chem. 13:4243–4252PubMedCrossRefGoogle Scholar
  16. Ottana R, Maccari R, Ciurleo R, Vigorita MG, Panico AM, Caedile V, Garufi F, Ronsisvalle S (2007) Synthesis and in vitro evaluation of 5-arylidene-3-hydroxyalkyl-2-phenylimino-4-thiazolidinones with antidegenerative activity on human chondrocyte cultures. Bioorg Med Chem. 15:7618–7625PubMedCrossRefGoogle Scholar
  17. Ottana R, Maccari R, Ciurleo R, Paoli P, Jacomelli M, Manao G, Camici G, Laggner C, Langer T (2009) 5-Arylidene-2-phenylimino-4-thiazolidinones as PTP1B and LMW-PTP inhibitors. Bioorg Med Chem. 17:1928–1937PubMedCrossRefGoogle Scholar
  18. Ronad PM, Noolvi MN, Sapkal S, Dharbhamulla S, Maddi VS (2010) Synthesis and antimicrobial activity of 7-(2-substituted phenylthiazolidinyl)-benzopyran-2-one derivatives. Eur J Med Chem 45:85–89PubMedCrossRefGoogle Scholar
  19. Sattigeri VJ, Soni A, Singhal S, Khan S, Pandya M, Bhateja P, Mathur T, Rattan A, Khanna JM, Mehta A (2005) Synthesis and antimicrobial activity of novel thiazolidinones. Arkivoc ii:46–59Google Scholar
  20. Sharma RC, Kumar D (2000) Synthesis of some new thiazolidin-4-ones as possible antimicrobial agents. J Indian Chem Soc. 77:492–493Google Scholar
  21. Vicini P, Geronikaki AA, Anastsia K, Incerti M, Zani F (2006) Synthesis and antimicrobial activity of novel 2-thiazolylimino-5-arylidene-4-thiazolidinones. Bioorg Med Chem. 14:3859–3864PubMedCrossRefGoogle Scholar
  22. Vicini P, Geronikaki AA, Incerti M, Zani F, Dearden J, Hewitt M (2008) 2-Heteroarylimino-5-benzylidene-4-thiazolidinones analogues of 2-thiazolylimino-5-benzylidene-4-thiazolidinones with antimicrobial activity: synthesis and structure-activity relationship. Bioorg Med Chem. 16:3714–3724PubMedCrossRefGoogle Scholar
  23. Williams DH (1996) The glycopeptide story: how to kill the deadly ‘Superbugs’. Nat Prod Rep 13:469–477PubMedCrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media, LLC 2011

Authors and Affiliations

  • Pooja Chawla
    • 1
  • Ranjit Singh
    • 2
  • Shailendra K. Saraf
    • 3
    Email author
  1. 1.Faculty of PharmacyBabu Banarasi Das National Institute of Technology and ManagementLucknowIndia
  2. 2.School of Pharmaceutical SciencesShobhit UniversityMeerutIndia
  3. 3.Faculty of PharmacyNorthern India Engineering CollegeLucknowIndia

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