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Synthesis, biological evaluation and molecular docking studies of N-acylheteroaryl hydrazone derivatives as antioxidant and anti-inflammatory agents

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Abstract

In search of new therapeutics with greater potency, three new series of 3-methyl-1-phenyl-1H-thieno[2,3-c]pyrazole-5-carbohydrazide derivatives have been synthesized and evaluated for their in vitro antioxidant and anti-inflammatory activities. The hydrazones bearing a core pyrazole, chromone and tetrazolo[1,5-a]quinoline scaffold showed promising activities. Interestingly, compounds 3a (EC50 = 06.00 ± 2.36) and 5c (EC50 = 07.21 ± 0.67) showed the most potent antioxidant activity, while compounds 3a (EC50 = 10.25 ± 1.08), 7b (EC50 = 10.50 ± 0.99) and 7c (EC50 = 11.18 ± 0.15) showed significant anti-inflammatory activity. Furthermore, molecular docking studies also revealed a significant correlation between the binding score and biological activity for these compounds to describe the molecular basis for the structure activity relationship (SAR) results. As these compounds are good cyclooxygenase inhibitors, isoenzyme inhibitory potency studies are warranted.

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Acknowledgments

The author P. S. M. thanks the University Grants Commission, New Delhi, India, and M. D. N. thanks the Council of Scientific and Industrial Research, New Delhi, India for providing a senior research fellowship, and also thanks the Department Head of the Department of Chemistry, Dr. Babasaheb Ambedkar Marathwada University, Aurangabad, Maharashtra for providing laboratory facilities. We are also thankful to the Haffkine Research Institute, Mumbai for providing biological activities.

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Authors and Affiliations

  1. Department of Chemistry, Dr. Babasaheb Ambedkar Marathwada University, Aurangabad, Maharashtra, 431 004, India

    Pravin S. Mahajan, Mukesh D. Nikam & Charansingh H. Gill

  2. Combi-Chem Resource Centre, CSIR-National Chemical Laboratory, Pune, 411008, India

    Vijay M. Khedkar & Dhiman Sarkar

  3. School of Chemical Sciences, Central University of Gujarat, Sector-30, Gandhinagar, 38200, Gujarat, India

    Prakash C. Jha

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  1. Pravin S. Mahajan
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Correspondence to Charansingh H. Gill.

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Mahajan, P.S., Nikam, M.D., Khedkar, V.M. et al. Synthesis, biological evaluation and molecular docking studies of N-acylheteroaryl hydrazone derivatives as antioxidant and anti-inflammatory agents. Res Chem Intermed 42, 2707–2729 (2016). https://doi.org/10.1007/s11164-015-2176-1

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