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Synthesis and structural elucidation of 1,2-naphthoquinone derivatives, Schiff base complexes and ternary complexes with 8-hydroxyquinoline: comparative studies of their antimicrobial, anti-inflammatory and anti-diabetic activities

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Abstract

Herein, a new derivative of 1,2-naphthoquinone with semicarbazide and its Schiff base complexes and ternary complexes have been synthesized with some transition metals such as Ni(II), Co(II) and Zn(II) by using the conventional reflux method and 8-hydroxyquinoline (8-HQ) as a secondary ligand for ternary complexes. All the compounds were characterized using elemental analysis, molar conductance, melting point, Powder XRD, magnetic moment measurement and various spectral techniques such as FTIR, 13C NMR, 1H NMR, and Mass Spectra. The specific peak of the enolic proton in 1H NMR spectra of the tridentate ligand (L) explained the amido-iminol tautomerism in semicarbazone. In addition, powder XRD analysis and TGA confirmed the crystalline nature and the thermal study of metal chelates, respectively. In vitro, all the compounds were screened for antimicrobial (against bacterial strains: S. aureus and E. coli; Fungal strain: A. niger), anti-diabetic and anti-inflammatory activity with their obtained IC50 values and compared with Acarbose and Aspirin standard drugs. Bioactivities of azomethine containing free ligand (L), their Schiff base complexes and ternary metal chelates were compared to each other. Free Schiff base (L) was found most potent for all selective bioactivities compared to their all-metal complexes, except Ni (II) Schiff base complex showed excellent activity against C. albicans.

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Acknowledgement

Department of Chemistry, University of Rajasthan, Jaipur, is gratefully acknowledged by all authors for its assistance and provision of research facilities. Also, we appreciate the Microbiology laboratory, SMS Medical College Jaipur, for biological investigations and MNIT, Jaipur, for spectral techniques and PXRD.

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Authors and Affiliations

  1. Department of Chemistry, University of Rajasthan, Jaipur, Rajasthan, 302004, India

    Seema, Shobhana Sharma, Poonam Yadav, Suman Kumari & Mamta Ranka

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Author Seema wrote the main manuscript text and Shobhana Sharma, Poonam Yadav and Suman Kumari contributed to data interpretation. All authors including corresponding author reviewed the manuscript.

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Correspondence to Mamta Ranka.

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Seema, Sharma, S., Yadav, P. et al. Synthesis and structural elucidation of 1,2-naphthoquinone derivatives, Schiff base complexes and ternary complexes with 8-hydroxyquinoline: comparative studies of their antimicrobial, anti-inflammatory and anti-diabetic activities. Transit Met Chem 48, 389–400 (2023). https://doi.org/10.1007/s11243-023-00551-w

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