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Synthesis and molecular docking study of pyrazole clubbed oxazole as antibacterial agents

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Abstract

We have developed a simple synthetic protocol for the preparation of novel 3-(3-(4-fluorophenyl)-1-phenyl-1H-pyrazol-4-yl)-5-arylisoxazoles. The structure of synthesized compounds was elucidated by spectral techniques like FT-IR, 1H-NMR, 13C-NMR, and mass. The novel bioactive compounds 3a-t were evaluated for in vitro antibacterial activity on several bacterial species. Compounds 3c (–4–NO2), 3o (–4–F), and 3r (–3,4–Cl2) exhibited good in vitro antibacterial activity. Furthermore, molecular docking on DNA gyrase subunit b could shed some light on the mechanism of action which can serve as a guide for lead optimization.

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Acknowledgement

One of the authors Prof. Nisheeth C Desai is thankful to UGC for awarding BSR faculty fellowship-2019 (No. F 18-1/2011 (BSR)) and financial assistant. The authors are grateful to the UGC, New Delhi, and Department of Science and Technology, New Delhi (DST-FIST-SR/FST/CSI-212/2010), for financial support under the NON-SAP and DST-FIST programs, respectively. The authors are also thankful to Schrödinger Inc. for providing the GLIDE program to carry out the molecular docking. Authors are also thankful to Priyanka Desai, founder of iScribblers for the English editing portion of the manuscript.

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Authors and Affiliations

  1. Division of Medicinal Chemistry, Department of Chemistry (DST-FIST Sponsored & UGC NON-SAP), Maharaja Krishnakumarsinhji Bhavnagar University, Mahatma Gandhi Campus, Bhavnagar, 364002, India

    Nisheeth C. Desai, Darshita V. Vaja & Surbhi B. Joshi

  2. Department of Pharmaceutical Chemistry, School of Pharmacy, Vishwakarma University, Pune, Maharashtra, 411 048, India

    Vijay M. Khedkar

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  1. Nisheeth C. Desai
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  2. Darshita V. Vaja
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Correspondence to Nisheeth C. Desai.

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11164_2020_4286_MOESM1_ESM.docx

Full experimental detail, IR, 1H and 13C NMR, Mass spectra, elemental analysis and molecular docking procedure have been provided in supplementary information. (DOCX 20230 kb)

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Desai, N.C., Vaja, D.V., Joshi, S.B. et al. Synthesis and molecular docking study of pyrazole clubbed oxazole as antibacterial agents. Res Chem Intermed 47, 573–587 (2021). https://doi.org/10.1007/s11164-020-04286-6

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