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<p>In this study, a previously synthesized Schiff base derivative, 3-phenyl-4-(2-acetoxy-3-methoxybenzylideneamino)-4,5-dihydro-1<i>H</i>-1,2,4-triazol-5-one (PAMT), was synthesized and its structural, electronic, and pharmacokinetic properties were comprehensively investigated using density functional theory (DFT). The molecular structure of the PAMT was further characterized by FT-IR, <sup>1</sup>H-NMR, and <sup>13</sup>C-NMR spectroscopic techniques. Theoretical IR and NMR spectra were computed using the Gaussian 09&#xa0;W program with the GIAO method, and the calculated results were systematically compared with the experimental data. Geometric optimizations were performed using the 6-311G+(d, p) basis set with the B3LYP and B3PW91 methods via Gaussian 09&#xa0;W software. Molecular Electrostatic Potential (MEP) maps were generated to determine the reactive sites and electrostatic surface properties of the molecule. As a result of frontier molecular orbital (FMO) analysis, the HOMO energy values were calculated as − 6.7040&#xa0;eV (B3LYP), − 7.0264&#xa0;eV (B3PW91), and LUMO energy values as 0.0708&#xa0;eV (B3LYP), 0.0321&#xa0;eV (B3PW91), respectively. These values provided important information about the chemical stability and reaction potential of the compound. Natural bonding orbital (NBO) analysis revealed that intramolecular charge transfer and hyperconjugative interactions in the compound contribute positively to the stability. In addition, electrophilic and nucleophilic centers were determined by Mulliken atomic charge distribution analyses. The nonlinear optical (NLO) properties of the compound were evaluated considering the dipole moment, polarizability, and first hyperpolarizability values, and PAMT was shown to be a potential candidate for NLO applications. Pharmacokinetic and drug-like property analyses using ADMETlab 2.0 demonstrated the compound’s suitability for drug development. Finally, to assess the compound’s potential effects on breast cancer targets, molecular docking studies were performed using proteins PDB ID: 3ERT and PDB ID: 5TOA. The binding energies obtained were − 8.30&#xa0;kcal/mol and − 8.90&#xa0;kcal/mol, respectively, indicating that PAMT exhibits high affinity for the target proteins. Considering all the data obtained, PAMT is considered a promising candidate in both pharmaceutical and advanced materials design.</p> Graphical abstract <p></p>

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Synthesis, in-silico molecular docking, ADMET profiling and DFT-based characterization of 3-phenyl-4-(2-acetoxy-3-methoxybenzylideneamino)-4,5-dihydro-1H-1,2,4-triazol-5-one

  • 期刊论文

  • 发表日期：

    2026年7月7日

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  • Kenan Gören,
  • Gül Kotan,
  • Muzaffer Alkan,
  • Abdurrahman Gürbüz,
  • Sevda Manap,
  • Haydar Yüksek

摘要

In this study, a previously synthesized Schiff base derivative, 3-phenyl-4-(2-acetoxy-3-methoxybenzylideneamino)-4,5-dihydro-1H-1,2,4-triazol-5-one (PAMT), was synthesized and its structural, electronic, and pharmacokinetic properties were comprehensively investigated using density functional theory (DFT). The molecular structure of the PAMT was further characterized by FT-IR, 1H-NMR, and 13C-NMR spectroscopic techniques. Theoretical IR and NMR spectra were computed using the Gaussian 09 W program with the GIAO method, and the calculated results were systematically compared with the experimental data. Geometric optimizations were performed using the 6-311G+(d, p) basis set with the B3LYP and B3PW91 methods via Gaussian 09 W software. Molecular Electrostatic Potential (MEP) maps were generated to determine the reactive sites and electrostatic surface properties of the molecule. As a result of frontier molecular orbital (FMO) analysis, the HOMO energy values were calculated as − 6.7040 eV (B3LYP), − 7.0264 eV (B3PW91), and LUMO energy values as 0.0708 eV (B3LYP), 0.0321 eV (B3PW91), respectively. These values provided important information about the chemical stability and reaction potential of the compound. Natural bonding orbital (NBO) analysis revealed that intramolecular charge transfer and hyperconjugative interactions in the compound contribute positively to the stability. In addition, electrophilic and nucleophilic centers were determined by Mulliken atomic charge distribution analyses. The nonlinear optical (NLO) properties of the compound were evaluated considering the dipole moment, polarizability, and first hyperpolarizability values, and PAMT was shown to be a potential candidate for NLO applications. Pharmacokinetic and drug-like property analyses using ADMETlab 2.0 demonstrated the compound’s suitability for drug development. Finally, to assess the compound’s potential effects on breast cancer targets, molecular docking studies were performed using proteins PDB ID: 3ERT and PDB ID: 5TOA. The binding energies obtained were − 8.30 kcal/mol and − 8.90 kcal/mol, respectively, indicating that PAMT exhibits high affinity for the target proteins. Considering all the data obtained, PAMT is considered a promising candidate in both pharmaceutical and advanced materials design.

Graphical abstract