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Synthesis and pharmacological evaluation of pyrazole derivatives containing sulfonamide moiety

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Abstract

A new series of N-[4-[N-[4-[5-[4-(benzyloxy)phenyl]-1-(substituted phenyl)-1H-pyrazol-3-yl]phenyl]sulfamoyl]phenyl]acetamide derivatives were synthesized and elucidated by spectral data. All the compounds were subjected to in vitro evaluation for anti-inflammatory (BSA anti-denaturation assay), antioxidant (DPPH radical scavenging assay) and in vivo screening for anti-inflammatory (carrageenan induced rat paw edema inhibition) activities. Selected active compounds were evaluated for ulcerogenic, lipid peroxidation, and LPS induced TNF-α production inhibition potential. The most active compound in the series showed an in vivo anti-inflammatory efficacy of 83.1 % when compared to diclofenac sodium (81.6 %). Evaluation of ulcer index and biochemical estimation for oxidative stress also revealed that this compound was safe on gastric mucosa and did not induce oxidative stress in tissues. When further tested for LPS induced TNF-α production inhibition in mice, it showed a better inhibition (ID50 = 6.23 mg/kg) when compared to standard inhibitor, SB 203580 (ID50 = 28.40 mg/kg). The p38α MAP kinase docking score of this active compound was also found to be better than that of SB 203580.

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Acknowledgments

The authors are grateful to Jamia Hamdard for providing infrastructure and other facilities. The author (Kanagasabai Somakala) is thankful to Department of Science and Technology Women Scientists Scheme-A (File No.: SR/WOS-A/CS-84/2013), New Delhi for providing financial assistance.

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Authors and Affiliations

  1. Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Hamdard University, New Delhi, 110062, India

    Kanagasabai Somakala & Mohammad Amir

  2. Department of Pharmaceutical Chemistry, University of Delhi (Delhi Institute of Pharmaceutical Sciences and Research), New Delhi, 110017, India

    Vidushi Sharma & Sharad Wakode

Authors
  1. Kanagasabai Somakala
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  2. Mohammad Amir
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  3. Vidushi Sharma
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  4. Sharad Wakode
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Corresponding author

Correspondence to Mohammad Amir.

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Somakala, K., Amir, M., Sharma, V. et al. Synthesis and pharmacological evaluation of pyrazole derivatives containing sulfonamide moiety. Monatsh Chem 147, 2017–2029 (2016). https://doi.org/10.1007/s00706-016-1694-x

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  • DOI: https://doi.org/10.1007/s00706-016-1694-x

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