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Synthesis of some novel isatin-thiazole conjugates and their computational and biological studies

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Abstract

The present work describes the synthesis of novel 3-[2-(5-phenyl-1,3-thiazol-2-yl)hydrazinyl]-1,3-dihydro-2H-indol-2-one derivatives 4(a-h) and the characterization of synthesized hybrids has been done using various spectroscopic techniques like FT-IR, NMR, and HRMS. Through computational study, some global parameters and molecular electrostatic potential (MEP) were analyzed. The solvatochromic UV–Vis absorption study was performed using various solvents and the optical bandgap of the synthesized compounds was determined by using Kubelka–Munk theory. The antimycobacterial activity of the synthesized compounds was evaluated against Mycobacterium tuberculosis and the results suggested that compounds 4d and 4e are effective inhibitors of Mycobacterium tuberculosis. The anti-inflammatory activity against MMP-2 and MMP-9 was determined using gelatin zymography; from the results, it was evaluated that the synthesized derivatives act as good anti-inflammatory agents.

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Acknowledgements

The authors are thankful to the Chairman, Department of Chemistry, Kuvempu University, Shankaraghatta, for providing the laboratory facilities and to the University of Mysore for providing spectra.

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Authors and Affiliations

  1. Department of P.G. Studies and Research in Chemistry, Jnana Sahyadri, Kuvempu University Shankaraghatta-577451, Shivamogga, Karnataka, India

    Navaneethgowda P. Veeranna, Yadav D. Bodke & Manjunatha Basavaraju

  2. Department of P.G. Studies and Research in Chemistry/Industrial Chemistry, Vijayanagara Sri Krishnadevaraya University, Ballari, -583105, Karnataka, India

    Kuntewale Mohiyouddin Mussuvir Pasha

Authors
  1. Navaneethgowda P. Veeranna
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  2. Yadav D. Bodke
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  3. Manjunatha Basavaraju
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  4. Kuntewale Mohiyouddin Mussuvir Pasha
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Contributions

Navaneethgowda P Veeranna: methodology, investigation, writing-original draft. Yadav D. Bodke: investigation, supervision, writing-review and editing. Manjunatha Basavaraju: writing and analysis. Kuntewale Mohiyouddin Mussuvir Pasha: DFT study and analysis.

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Correspondence to Yadav D. Bodke.

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DFT studies were performed by using B3LYP level with a basic set 6–31 G(d.p).

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The authors declare no competing interests.

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Veeranna, N.P., Bodke, Y.D., Basavaraju, M. et al. Synthesis of some novel isatin-thiazole conjugates and their computational and biological studies. Struct Chem 33, 897–906 (2022). https://doi.org/10.1007/s11224-022-01892-5

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  • DOI: https://doi.org/10.1007/s11224-022-01892-5

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