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Design and synthesis of butenolide-based amide derivatives as anti-inflammatory agents

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Abstract

Butenolide-based eighteen new amide derivatives (1–18) have been synthesized and evaluated for anti-inflammatory activity. The compounds 9, 17 and 4 exhibited significant in vivo inhibition of 84.69, 76.52 and 76.22 % inflammation, respectively, after 5 h without causing any damage to stomach and liver in comparison with the standard drug indomethacin which showed 79.04 % inhibition. The compounds showing potent anti-inflammatory activity were further evaluated for ex vivo TNF-α suppression. Compounds 9, 17 and 4 significantly suppressed TNF-α concentration to 74.83, 71.74 and 67.11 % as compared to indomethacin which exhibited a suppression of 69.01 %. Compounds 9 and 17 were also found to suppress the expression of COX-2 and NF-κB in the paw tissue. Moreover, compound 9 showed significant analgesic activity (57.03 %) which was comparable to indomethacin (61.03 %).

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Acknowledgments

The authors thank Vice Chancellor, Dr. G. N. Qazi for providing necessary facilities to the Department of Chemistry. Yakub Ali acknowledges Hamdard National Fellowship (HNF) for providing financial assistance.

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Authors and Affiliations

  1. Department of Chemistry, Faculty of Science, Jamia Hamdard (Hamdard University), New Delhi, 110 062, India

    Yakub Ali, Mohammad Sarwar Alam, Hinna Hamid, Sameena Bano, Chetna Kharbanda, Syed Nazreen & Saqlain Haider

  2. Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Jamia Hamdard (Hamdard University), New Delhi, 110 062, India

    Asif Husain

  3. CSIR Unit for Research and Development of Information Products, Pune, 411038, India

    Abhijeet Dhulap

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  1. Yakub Ali
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Correspondence to Mohammad Sarwar Alam.

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Ali, Y., Alam, M.S., Hamid, H. et al. Design and synthesis of butenolide-based amide derivatives as anti-inflammatory agents. Med Chem Res 24, 3775–3784 (2015). https://doi.org/10.1007/s00044-015-1404-y

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  • DOI: https://doi.org/10.1007/s00044-015-1404-y

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