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New pentacoordinated diorganotin(IV) complexes of o-aminophenol based Schiff base ligands: Synthesis, characterization, antioxidant, antimicrobial and molecular docking studies

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Abstract

In the present study, sixteen new diorganotin(IV) complexes of the general formula R2SnL1−4 where, R = methyl, ethyl, butyl phenyl and L1 = 4-chloro-2-(((2-hydroxy-5-(tert-pentyl)phenyl)imino)methyl)phenol; L2 = 3-ethoxy-2-(((2-hydroxy-5-(tert-pentyl)phenyl)imino)methyl)phenol; L3 = 4-bromo-2-(((2-hydroxy-5-(tert-pentyl)phenyl)imino)methyl)phenol; L4 = 4-nitro-2-(((2-hydroxy-5-(tert-pentyl)phenyl)imino)methyl)phenol) were synthesized and characterized by elemental analysis, molar conductance measurements, FT-IR, mass spectrometry, NMR (1H, 13C, and 119Sn), powder XRD, TGA, SEM and EDAX. Spectroscopic data elucidated that Schiff base ligands coordinate to the tin metal via ONO donor atoms in a tridentate manner. The synthesized compounds were explored for their antioxidant potential by performing DPPH assay and the data obtained demonstrated that complex 12 (IC50 = 2.57 µM) showed good antioxidant potential. The prepared compounds were also assessed for antimicrobial potential against bacterial and fungal strains and especially complex 20 being most effective against Escherichia coli (MIC = 0.0026 µmol/mL) and Candida albicans (MIC = 0.0052 µmol/mL). Further, molecular docking studies of the most potent complex 20 was performed to investigate the preferred binding modes in the active site of enzymes E. coli DNA Gyrase and C. albicans sterol 14-alpha demethylase. Additionally, in silico studies were conducted to assess the drug-like properties of the compounds (1–20), and the results indicated that the compounds have the potential to be utilized as orally active drugs.

Graphical abstract

New o-aminophenol based ligands and their diorganotin(IV) complexes were synthesized, and successfully characterized. The synthesized compounds were examined for their in vitro antioxidant and antimicrobial activities. Additionally, molecular docking studies were conducted specifically on the most promising compounds identified in the antimicrobial assay.

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Funding

The research received financial support from the Council of Scientific and Industrial Research (CSIR), New Delhi, in the form of a JRF-SRF fellowship with reference number 09/752(0120)/2021-EMR-I.

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Authors and Affiliations

  1. Department of Chemistry, Guru Jambheshwar University of Science and Technology (GJUS&T), Hisar, Haryana, 125001, India

    Pinki Barwa, Sonika Asija, Yogesh Deswal, Naresh Kumar & Jai Devi

  2. Department of Pharmaceutical Sciences, Guru Jambheshwar University of Science and Technology, Hisar, Haryana, 125001, India

    Ashwani Kumar

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  1. Pinki Barwa
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Contributions

PB: Writing-original draft, Conceptualization, Methodology, Data curation, Investigation. SA: Supervision, Formal analysis, Validation. YD: Writing-original draft, Writing-review and editing, Software, Data curation, Validation. NK: Formal analysis. AK: Software. JD: Investigation.

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Correspondence to Sonika Asija.

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Barwa, P., Asija, S., Deswal, Y. et al. New pentacoordinated diorganotin(IV) complexes of o-aminophenol based Schiff base ligands: Synthesis, characterization, antioxidant, antimicrobial and molecular docking studies. Res Chem Intermed 49, 3411–3440 (2023). https://doi.org/10.1007/s11164-023-05053-z

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