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<p>In this study, benzoyl isothiocyanate was first obtained by the reaction of benzoyl chloride with ammonium thiocyanate. The ligand N-(2-amino-5-methylpyridine)-N′-benzoylthiourea (HL) was then synthesized by condensing benzoyl isothiocyanate with 2-amino-5-methylpyridine. Subsequently, mixed-ligand metal(II) complexes were prepared by reacting HL with L-phenylalanine or L-alanine in the presence of copper(II) or zinc(II) acetate dihydrate salts. The HL ligand was characterized by elemental analysis, FT-IR, <sup>1</sup>H and <sup>13</sup>C NMR spectroscopy. The metal complexes were characterized by elemental analysis, FT-IR, molar conductivity, magnetic susceptibility, and thermal analysis, supported by DFT calculations. Among the complexes, complex [ZnL(phe)(H<sub>2</sub>O)<sub>2</sub>](2) stood out due to its high stability, low toxicity (LD<sub>50</sub>=3200&#xa0;mg/kg, toxicity class 5), and favorable ADMET profile. Molecular docking studies against lipoteichoic acid synthase (2W5T, Gram-positive) revealed that complex [ZnL(phe)(H<sub>2</sub>O)<sub>2</sub>](2) exhibited a strong binding affinity, with a docking score of -9.7&#xa0;kcal/mol. This in silico finding was consistent with the in vitro antibacterial results, where complex [ZnL(phe)(H<sub>2</sub>O)<sub>2</sub>](2) showed the highest zone of inhibition (16&#xa0;mm) against Staphylococcus aureus. Complex [CuL(phe)(H<sub>2</sub>O)<sub>2</sub>](1) demonstrated superior antioxidant activity, with an IC₅₀ value of 6.91&#xa0;µg/mL in the ABTS assay, outperforming the reference antioxidants. Complexes [CuL(Ala)(H<sub>2</sub>O)<sub>2</sub>](3) and [CuL<sub>2</sub>(H<sub>2</sub>O)<sub>2</sub>](4) exhibited potent antibacterial activity against Pseudomonas aeruginosa, with MIC values of 256&#xa0;µg/mL. These results demonstrate that varying the metal center and co-ligand in mixed-ligand complexes can yield distinct bioactivity profiles, from potent antioxidant effects to targeted antibacterial action.</p>

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A novel benzoylthiourea derivative and its ternary complexes: Experimental, theoretical, antibacterial, antioxidant, and docking studies

  • 期刊论文

  • 出版模式：

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  • 发表日期：

    2026年5月25日

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  • Tagina Jalili Qebchaq,
  • İskender Muz,
  • Bahar Tuba Fındık,
  • Fatma Karipcin

摘要

In this study, benzoyl isothiocyanate was first obtained by the reaction of benzoyl chloride with ammonium thiocyanate. The ligand N-(2-amino-5-methylpyridine)-N′-benzoylthiourea (HL) was then synthesized by condensing benzoyl isothiocyanate with 2-amino-5-methylpyridine. Subsequently, mixed-ligand metal(II) complexes were prepared by reacting HL with L-phenylalanine or L-alanine in the presence of copper(II) or zinc(II) acetate dihydrate salts. The HL ligand was characterized by elemental analysis, FT-IR, 1H and 13C NMR spectroscopy. The metal complexes were characterized by elemental analysis, FT-IR, molar conductivity, magnetic susceptibility, and thermal analysis, supported by DFT calculations. Among the complexes, complex [ZnL(phe)(H2O)2](2) stood out due to its high stability, low toxicity (LD50=3200 mg/kg, toxicity class 5), and favorable ADMET profile. Molecular docking studies against lipoteichoic acid synthase (2W5T, Gram-positive) revealed that complex [ZnL(phe)(H2O)2](2) exhibited a strong binding affinity, with a docking score of -9.7 kcal/mol. This in silico finding was consistent with the in vitro antibacterial results, where complex [ZnL(phe)(H2O)2](2) showed the highest zone of inhibition (16 mm) against Staphylococcus aureus. Complex [CuL(phe)(H2O)2](1) demonstrated superior antioxidant activity, with an IC₅₀ value of 6.91 µg/mL in the ABTS assay, outperforming the reference antioxidants. Complexes [CuL(Ala)(H2O)2](3) and [CuL2(H2O)2](4) exhibited potent antibacterial activity against Pseudomonas aeruginosa, with MIC values of 256 µg/mL. These results demonstrate that varying the metal center and co-ligand in mixed-ligand complexes can yield distinct bioactivity profiles, from potent antioxidant effects to targeted antibacterial action.