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Synthesis of 1-(4-aminosulfonylphenyl)-3,5-diarylpyrazoline derivatives as potent antiinflammatory and antimicrobial agents

Abstract

A new series of 1-(4-aminosulfonylphenyl)-3,5-diaryl pyrazolines (5) was synthesized by the reaction of appropriate chalcones 3 with 4-hydrazinobenzenesulfonamide hydrochloride (4) in ethanol in the presence of catalytic amount of acetic acid. All newly synthesized compounds were in vivo evaluated for their antiinflammatory activity using carrageenan-induced rat paw edema assay. Five of the newly synthesized compounds, 5d, 5g, 5h, 5i, and 5m displayed significant antiinflammatory activity, greater than 55% inhibition 3 h after the carrageenan injection. All the newly synthesized compounds were evaluated for their in vitro antimicrobial activity against two Gram-positive bacteria (Staphylococcus aureus and Bacillus subtilis); two Gram-negative bacteria (Escherichia coli and Pseudomonas aeruginosa), and two yeast (Candida albicans and Saccharomyces cerevisiae). Some of the newly synthesized compounds 5a, 5f, 5g, 5h, 5j, and 5k showed excellent antifungal activity, greater than the reference drug amphotericin B, against Saccharomyces cerevisiae.

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Acknowledgments

One of the authors (S.K.) is grateful to the University Grants Commission (UGC), New Delhi for the award of senior research fellowship. Defence Research and Development Organization (DRDO), New Delhi is acknowledged for financial support in the form of a research project.

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Correspondence to Pawan K. Sharma.

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Sharma, P.K., Kumar, S., Kumar, P. et al. Synthesis of 1-(4-aminosulfonylphenyl)-3,5-diarylpyrazoline derivatives as potent antiinflammatory and antimicrobial agents. Med Chem Res 21, 2945–2954 (2012). https://doi.org/10.1007/s00044-011-9823-x

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Keywords

  • Chalcones
  • 4-Hydrazinobenzenesulfonamide hydrochloride
  • 1-(4-aminosulfonylphenyl)-3
  • 5-Diaryl-2-pyrazoline
  • Antiinflammatory
  • Antimicrobial