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Synthesis and characterization of hydrazones and their transition metal complexes: antimicrobial, antituberculosis and antioxidant activity

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Abstract

In the search of potential bioactive compounds, we have synthesized new Co(II), Ni(II), Cu(II) and Zn(II) metal complexes of hydrazone ligands derived by the condensation of benzyl carbazate with different derivatives of salicylaldehyde. Further, the synthesized compounds were precisely characterized by several physicochemical (TGA, powder XRD, SEM, EDAX) and spectroscopic techniques (FTIR, UV–Vis, NMR, mass spectrometry, ESR, fluorescence). Spectroscopic techniques proposed the octahedral geometry of the complexes coordinating via enolic oxygen atom, azomethine nitrogen atom, phenolic oxygen atom and oxygen atom of water molecules. The surface morphology of the ligands was distinct from metal complexes as revealed by SEM analysis. Further, serial dilution methodology was used to test the in vitro antimicrobial activity of the compounds (1–20) against four bacterial (E. coli, S. aureus, P. aeruginosa and B. subtilis) and two fungal (C. albicans and A. niger) pathogens and antituberculosis activity was assessed against M. tuberculosis H37RV (MTCC 200) strain using Lowenstein–Jensen (L. J.) slope technique while the DPPH assay was employed to examine the antioxidant activity of the synthesized compounds. The results of the pharmacological activities revealed that ligand H2L2 (2) and its Cu(II) and Zn(II) (11,12) complexes have potent antimicrobial and antitubercular activities while hydrazone ligand H2L4 (4) and its Cu(II) (19) complex show good efficiency for decolourizing purple colour of DPPH solution. In addition, in silico ADME study was conducted on the compounds which revealed that compounds have the potential to be administrated orally as active drugs.

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Acknowledgements

The author, Ms. Tanisha Arora (File no. 09/752(0118)/2020-EMR-I), is highly grateful to CSIR-Human Resource Development Group, New Delhi, for financial support and the author is also thankful to Dr. A.P.J. Abdul Kalam C.I.L and Department of Chemistry, Guru Jambheshwar University of Science & Technology, Hisar (Haryana), for providing research facilities.

Funding

The author, Ms. Tanisha Arora (File No. 09/752(0118)/2020-EMR-I), is highly grateful to CSIR-Human Resource Development Group, New Delhi, for financial support in the form of SRF (senior research fellowship).

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Authors and Affiliations

  1. Department of Chemistry, Guru Jambheshwar University of Science and Technology, Hisar, 125001, Haryana, India

    Tanisha Arora, Jai Devi, Ankit Boora, Bharti Taxak & Swati Rani

  2. ICAR-National Research Centre on Equines, Hisar, Haryana, 125001, India

    Swati Rani

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  1. Tanisha Arora
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Contributions

Tanisha Arora contributed to writing original draft, investigation, data curation and methodology. Jai Devi contributed to supervision, validation, data curation, and writing—review and editing. Ankit Boora, Bharti Taxak and Swati Rani contributed to formal analysis.

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Correspondence to Jai Devi.

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Arora, T., Devi, J., Boora, A. et al. Synthesis and characterization of hydrazones and their transition metal complexes: antimicrobial, antituberculosis and antioxidant activity. Res Chem Intermed 49, 4819–4843 (2023). https://doi.org/10.1007/s11164-023-05116-1

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