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New organosulfur metallic compounds as potent drugs: synthesis, molecular modeling, spectral, antimicrobial, drug likeness and DFT analysis

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Abstract

During the present investigation, two new sulfonamide-based Schiff base ligands, 4-{[(2-hydroxy-3-methoxyphenyl)methylidene]amino}-N-(1,3-thiazol-2-yl)benzene-1-sulfonamide (L1) and 4-{[1-(2-hydroxyphenyl)ethylidene]amino}-N-(1,3-thiazol-2-yl)benzene-1-sulfonamide (L2), have been synthesized and coordinated with the transition metals (V, Fe, Co, Ni, Cu and Zn). The ligands were characterized by their physical (color, melting point, yield and solubility), spectral (UV–Vis, FT-IR, LC–MS, 1H NMR and 13C NMR) and elemental data. The structures of the metal complexes (1)–(12) were evaluated through their physical (magnetic and conductance), spectral (UV–Vis, FT-IR and LC–MS) and elemental data. The molecular geometries of ligands and their selected metal complexes were optimized at their ground state energies by B3LYP level of density functional theory (DFT) utilizing 6-311+G (d, p) and LanL2DZ basis set. The first principle study has been discussed for the electronic properties, the molecular electrostatic possibilities as well as the quantum chemical identifiers. An obvious transition of intramolecular charge had been ascertained from the occupied to the unoccupied molecular orbitals. The UV–Vis analysis was performed through time-dependent density functional theory (TD-DFT) by CAM-B3LYP/6-311+G (d, p) function. The in vitro antimicrobial activity was studied against two fungal (Aspergillus niger and Aspergillus flavus) and four bacterial (Staphylococcus aureus, Klebsiela pneumoniae, Escherichia coli and Bacillus subtilis) species. The antioxidant activity was executed as antiradical DPPH scavenging activity (%), total iron reducing power (%) and total phenolic contents (mg GAE g−1). Additionally, enzyme inhibition activity was done against four enzymes (Protease, α-Amylase, Acetylcholinesterase and Butyrylcholinesterase). All the synthetic products exhibited significant bioactivity which were found to enhance upon chelation due to phenomenon of charge transfer from metal to ligand.

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Funding

This research work had the financial support from the Higher Education Commission (HEC), Islamabad, Pakistan in the form of their NRPU Project # 7800.

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Authors and Affiliations

  1. Department of Chemistry, University of Gujrat, Gujrat, 50700, Pakistan

    Abrar Ul Hassan, Sajjad Hussain Sumrra, Muhammad Nadeem Zafar, Muhammad Faizan Nazar & Ehsan Ullah Mughal

  2. Department of Chemistry, Division of Science and Technology, University of Education, Lahore, Multan Campus, Pakistan

    Muhammad Faizan Nazar

  3. Department of Chemistry, Quaid-i-Azam University, Islamabad, 45320, Pakistan

    Muhammad Naveed Zafar

  4. Health Biotechnology Division, National Institute for Biotechnology and Genetic Engineering (NIBGE), Faisalabad, Pakistan

    Mazhar Iqbal

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  1. Abrar Ul Hassan
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Hassan, A.U., Sumrra, S.H., Zafar, M.N. et al. New organosulfur metallic compounds as potent drugs: synthesis, molecular modeling, spectral, antimicrobial, drug likeness and DFT analysis. Mol Divers 26, 51–72 (2022). https://doi.org/10.1007/s11030-020-10157-4

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