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Biological evaluation and in silico molecular docking study of a new series of thiazol-2-yl-hydrazone conglomerates

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Abstract

A new series of hybridized thiazol-2-yl-hydrazone derivatives having diverse substituents were designed, synthesized, and screened for their anti-inflammatory property by a carrageenan-induced paw edema method. The compounds 11a, 11b, 11c, 11d, 11e, 11g, 11m and 11p revealed significant inhibition when compared to Diclofenac sodium. Subsequently, two highly potent compounds (11d and 11e) were evaluated for their cytotoxic effect on the tumor cell line. The binding interactions of thiazol-2-yl-hydrazones with the cyclooxygenase-2 (COX-2) protein (PDB: 3LN1) displayed effective interactions with Arg-120, Tyr-385 and Tyr-355 amino acids, the main criteria of the COX-2 inhibitor. In addition, all the compounds showed moderate to good in vitro antibacterial activity. Most active benzyloxy derivatives were also tested to understand the radical scavenging efficacy by the 2,2-diphenyl-1-picrylhydrazyl method.

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Acknowledgements

The authors are obliged to Mangalore University for providing the facility and also grateful to Mysore University and SAIF Cochin for providing spectral data. The authors are also grateful to Vaishali M. Rai (Department of Microbiology, Mangalore University, Mangaluru), for the needful help.

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Authors and Affiliations

  1. Department of Chemistry, Mangalore University, Mangalagangothri, Mangaluru, Karnataka, 574199, India

    Mahima Bhat & Boja Poojary

  2. Medicinal Chemistry Research Laboratory, Acharya and B. M. Reddy College of Pharmacy, Bangalore, Karnataka, 560090, India

    P. M. Gurubasavaraja Swamy

  3. Department of Pharmaceutical Chemistry, NGSM Institute of Pharmaceutical Sciences Nitte University, Mangaluru, Karnataka, India

    B. C. Revanasiddappa & M. Vijay Kumar

  4. Department of Chemistry, SDM College (Autonomus), Ujire, Karnataka, 574240, India

    Vasantha Kumar

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  1. Mahima Bhat
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Correspondence to Boja Poojary.

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This article contains the studies performed on animals (mice). The appropriate care and use of animals were performed according to the international, national, and institutional guidelines. The study on mice was in accordance with the ethical standards of the institutional and national research committee. This study does not include any human participants. Ethical No. SCSCP/IAEC/08/2016-2017.

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Bhat, M., Gurubasavaraja Swamy, P.M., Poojary, B. et al. Biological evaluation and in silico molecular docking study of a new series of thiazol-2-yl-hydrazone conglomerates. Res Chem Intermed 44, 2779–2805 (2018). https://doi.org/10.1007/s11164-018-3261-z

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