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Synthesis and antimicrobial activity of 5-((3-aryl-1-phenyl-1H-pyrazol-4-yl)methylene)thiazolidine-2,4-diones

Abstract

A series of 5-((3-aryl-1-phenyl-1H-pyrazol-4-yl)methylene)thiazolidine-2,4-diones was synthesized by Knoevenagel condensation of various 3-aryl-1-phenyl-1H-pyrazole-4-carbaldehydes (1ah) with thiazolidine-2,4-dione (2) in ethanol in the presence of piperidine. All compounds were screened for their in vitro antibacterial (Staphylococcus aureus, Bacillus subtilis, Pseudomonas aeruginosa and Escherichia coli) activity and compared with the commercially available antibiotic, ciprofloxacin. All compounds showed good activity against gram-positive bacteria, however, none of the compounds were found to be effective against gram-negative bacteria. Compound 3g was found to be most potent member among all the compounds showing MIC of 16 μg/ml against S. aureus and 32 μg/ml against B. subtilis. All the synthesized compounds were also tested for their in vitro antifungal (Aspergillus niger and A. flavus) activity and compared with commercially available fluconazole. They showed excellent antifungal activity. Compounds 3b, 3e, 3f and 3g were active against both fungi showing more than 60% inhibition. Compound 3e was found to be superior to the reference drug.

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Acknowledgments

The authors are thankful to Council of Scientific & Industrial Research (CSIR 01(2186)/07/EMR-II), New Delhi, India for providing financial assistance to carry out this study. One of the authors Deepak K. Aneja is grateful to the UGC, New Delhi, India for providing JRF. Thanks are due to CDRI, Lucknow for carrying out elemental analysis.

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Correspondence to Om Prakash.

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Prakash, O., Aneja, D.K., Lohan, P. et al. Synthesis and antimicrobial activity of 5-((3-aryl-1-phenyl-1H-pyrazol-4-yl)methylene)thiazolidine-2,4-diones. Med Chem Res 21, 2961–2968 (2012). https://doi.org/10.1007/s00044-011-9829-4

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Keywords

  • Pyrazole
  • Thiazolidine-2,4-dione
  • Antibacterial activity
  • Antifungal activity