Medicinal Chemistry Research

, Volume 21, Issue 10, pp 3263–3271

Effect of chloro and fluoro groups on the antimicrobial activity of 2,5-disubstituted 4-thiazolidinones: a comparative study

Original Research

DOI: 10.1007/s00044-011-9864-1

Cite this article as:
Chawla, P., Singh, R. & Saraf, S.K. Med Chem Res (2012) 21: 3263. doi:10.1007/s00044-011-9864-1

Abstract

The article reports the synthesis of a series comprising of twenty-one 2,5-disubstituted-4-thiazolidinone derivatives, bearing 3-chloro-4-fluorophenyl imino, 4-chlorophenyl imino and 3-chlorophenyl imino groups at position-2 and substituted arylidene groups at position-5. The title compounds were obtained in high yields through Knoevenagel condensation and evaluated for antimicrobial activity against B. subtilis, S. aureus, P. aeruginosa, E. coli, and C. albicans. Success of the synthesis was confirmed through spectral analysis. The newly synthesized compounds exhibited promising antibacterial activity but no antifungal activity. SAR studies revealed that the presence of a fluoro group in addition to a chloro group had a marked influence on the antibacterial activity.

Keywords

4-Thiazolidinones Arylidene Spectral analysis Imino Knoevenagel condensation Antimicrobial 

Copyright information

© Springer Science+Business Media, LLC 2011

Authors and Affiliations

  • Pooja Chawla
    • 1
  • Ranjit Singh
    • 2
  • Shailendra K. Saraf
    • 3
  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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