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Microwave-Assisted Synthesis, Characterization, Docking Studies and Molecular Dynamic of Some Novel Phenyl Thiazole Analogs as Xanthine Oxidase Inhibitor

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Abstract

A series of novel substituted 2-(4-bromophenyl)-4-phenylthiazole compounds 5a–h were synthesized by a simplified two-step process. First, the selective and effective α-bromination of substituted acetophenone moieties with N-bromo succinamide was done followed by treating of substituted 2-bromo-1-phenylethan-1-one with 4-bromobenzothiamide under microwave irradiation. The structures of the newly synthesized compounds were confirmed by IR, 1H NMR, 13C NMR, mass spectra and C, H, N analysis. Further, all the synthesized compounds 5a–h were evaluated for xanthine oxidase inhibition. Among all the tested compounds, 5f was found to be highly potent (IC50 = 0.100 ± 0.08 µM) followed by 5e (IC50 = 0.145 ± 1.42 µM), compared to the standard allopurinol (IC50 = 0.150 ± 0.07 µM), which is evident from in vitro and in silico analysis.

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Acknowledgements

All authors thank the University of Mysore, Mysuru, and JSS Academy of Higher Education and Research, Mysuru, for providing facilities to carry out the biological activity. Shaukath Ara Khanum thankfully acknowledges the financial support provided by VGST, Bangalore, under CISEE Programme [Project sanction order: No. VGST/CISEE/282].

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Authors and Affiliations

  1. Department of Chemistry, Yuvaraja’s College (Autonomous), University of Mysore, Mysuru, Karnataka, 570005, India

    Mahima Jyothi & Shaukath Ara Khanum

  2. Department of Medical Science, Community College-Abs, Abs, Yemen

    Hussien Ahmed Khamees

  3. Department of Biotechnology and Bioinformatics, JSS Academy of Higher Education and Research, Mysuru, Karnataka, 570015, India

    Shashank M. Patil & Ramith Ramu

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  1. Mahima Jyothi
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  2. Hussien Ahmed Khamees
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Correspondence to Shaukath Ara Khanum.

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Jyothi, M., Khamees, H.A., Patil, S.M. et al. Microwave-Assisted Synthesis, Characterization, Docking Studies and Molecular Dynamic of Some Novel Phenyl Thiazole Analogs as Xanthine Oxidase Inhibitor. J IRAN CHEM SOC 19, 3919–3933 (2022). https://doi.org/10.1007/s13738-022-02574-z

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