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Abstract <p>A new pyrazolone-condensed azo&#xa0;ligand with a 4-(2-hydroxyethylsulfonyl)phenyl group was designed and coordinated with Cu(II), Mn(II), Fe(II), Co(II), and Ni(II) transition-metal ions to produce a series of metal complexes with a 1:2 stoichiometry. The ligand was characterized by <sup>1</sup>H and <sup>13</sup>C NMR, HRMS, FT-IR, UV–visible spectroscopy, and elemental analysis, whereas the complexes were characterized by FT-IR, UV–visible spectroscopy, ESI–MS, magnetic susceptibility evaluation, and elemental analysis. The octahedral geometry of the complexes was anticipated by the integrated magnetic, spectroscopic, and computational results. In line with the experimental findings, Density Functional Theory (DFT) simulations confirmed the decreased HOMO–LUMO energy gaps, improved electronic delocalization, effective ligand-to-metal charge transfer, and partial covalent character inside the coordination sphere. The compounds' biological efficacy was investigated using in vitro antibacterial and anticancer studies. The in vitro anticancer activity of all compounds was assessed against the A549 human lung adenocarcinoma cell line, with doxorubicin serving as the standard reference medicine. The ligand (IC<sub>50</sub> = 52.38&#xa0;μM) and its Cu(II) complex (IC<sub>50</sub> = 58.12&#xa0;μM) showed substantial cytotoxicity against A549 cells compared to other synthesized compounds. Both compounds demonstrated promising in vitro cytotoxicity, as seen by their reduced IC<sub>50</sub> values compared to the reference drug&#xa0;doxorubicin (IC<sub>50</sub> = 169.3&#xa0;μM). The antibacterial evaluation showed that while the Fe(II), Mn(II), and Cu(II) complexes showed intermediate activity against fungal strains, the Ni(II) and Co(II) complexes showed higher efficacy against bacterial strains. With an emphasis on their importance as multifunctional scaffolds for the development of coordination compounds with medicinal potential, this comprehensive theoretical and experimental study demonstrated that pyrazolone-based transition metal complexes have tunable electronic properties and promising medicinal activities.</p> Graphical abstract <p></p>

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Sulfonyl-substituted pyrazolone-based metal complexes as anticancer and antimicrobial scaffolds: design, synthesis, spectral characterization, and DFT investigations

  • 期刊论文

  • 发表日期：

    2026年7月20日

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  • Parth H. Gajiwala,
  • Mitesh B. Solanki,
  • Pooja A. Chauhan,
  • Tarulata N. Chhowala

摘要

Abstract

A new pyrazolone-condensed azo ligand with a 4-(2-hydroxyethylsulfonyl)phenyl group was designed and coordinated with Cu(II), Mn(II), Fe(II), Co(II), and Ni(II) transition-metal ions to produce a series of metal complexes with a 1:2 stoichiometry. The ligand was characterized by 1H and 13C NMR, HRMS, FT-IR, UV–visible spectroscopy, and elemental analysis, whereas the complexes were characterized by FT-IR, UV–visible spectroscopy, ESI–MS, magnetic susceptibility evaluation, and elemental analysis. The octahedral geometry of the complexes was anticipated by the integrated magnetic, spectroscopic, and computational results. In line with the experimental findings, Density Functional Theory (DFT) simulations confirmed the decreased HOMO–LUMO energy gaps, improved electronic delocalization, effective ligand-to-metal charge transfer, and partial covalent character inside the coordination sphere. The compounds' biological efficacy was investigated using in vitro antibacterial and anticancer studies. The in vitro anticancer activity of all compounds was assessed against the A549 human lung adenocarcinoma cell line, with doxorubicin serving as the standard reference medicine. The ligand (IC50 = 52.38 μM) and its Cu(II) complex (IC50 = 58.12 μM) showed substantial cytotoxicity against A549 cells compared to other synthesized compounds. Both compounds demonstrated promising in vitro cytotoxicity, as seen by their reduced IC50 values compared to the reference drug doxorubicin (IC50 = 169.3 μM). The antibacterial evaluation showed that while the Fe(II), Mn(II), and Cu(II) complexes showed intermediate activity against fungal strains, the Ni(II) and Co(II) complexes showed higher efficacy against bacterial strains. With an emphasis on their importance as multifunctional scaffolds for the development of coordination compounds with medicinal potential, this comprehensive theoretical and experimental study demonstrated that pyrazolone-based transition metal complexes have tunable electronic properties and promising medicinal activities.

Graphical abstract