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Synthesis and biological evaluation of pyrazole chalcones and derived bipyrazoles as anti-inflammatory and antioxidant agents

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Abstract

A series of bipyrazoles functionalized with sulfonamide, N1,N3-disubstituted sulfonylurea, sulfonylthiourea pharmacophores, and some derived thiazolidinone and thiazoline ring systems were synthesized. The structures of the newly synthesized compounds were substantiated by analytical and diverse spectroscopic data. The anti-inflammatory and antioxidant activity of some of the newly synthesized compounds were tested and the results reveled that compounds 14, 16, 20, 24 and 25 proved to be the most active anti-inflammatory agents according to the Carrageenan-induced rat paw edema bioassay. Whereas, the analogs 14, 16 and 24 were able to exhibit good to moderate antioxidant activity in the DPPH radical-scavenging assay. Hence, compounds 14, 16 and 24 can be considered as lead structures for dual anti-inflammatory and antioxidant activities.

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Acknowledgments

This project was funded by Saudi Basic Industries Corporation (SABIC) and the Deanship of Scientific Research (DSR), King Abdulaziz University, Jeddah, under grant no. (MS/14/117/1433). The authors, therefore, acknowledge with thanks SABIC and DSR technical and financial support. Extendable thanks are conveyed to I. F. Mahmoud (Pharmacist) for his valuable assistance during carrying out the biological assays. The authors have no conflict of interest.

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Authors and Affiliations

  1. Department of Chemistry, Faculty of Science, King Abdulaziz University, P.O. Box 80203, Jeddah, 21589, Saudi Arabia

    Hassan M. Faidallah & Khalid A. Khan

  2. Department of Pharmaceutical Chemistry, Faculty of Pharmacy, King Abdulaziz University, P.O. Box 80260, Jeddah, 21589, Saudi Arabia

    Sherif A. F. Rostom

  3. Department of Pharmaceutical Chemistry, Faculty of Pharmacy, University of Alexandria, Alexandria, 21521, Egypt

    Sherif A. F. Rostom

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  1. Hassan M. Faidallah
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  2. Sherif A. F. Rostom
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  3. Khalid A. Khan
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Correspondence to Hassan M. Faidallah.

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Faidallah, H.M., Rostom, S.A.F. & Khan, K.A. Synthesis and biological evaluation of pyrazole chalcones and derived bipyrazoles as anti-inflammatory and antioxidant agents. Arch. Pharm. Res. 38, 203–215 (2015). https://doi.org/10.1007/s12272-014-0392-7

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  • DOI: https://doi.org/10.1007/s12272-014-0392-7

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