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<p>Imidazole derivatives are important heterocyclic compounds known for their broad pharmacological activities, including antimicrobial, anti-inflammatory, antitumor, analgesic, anti-HIV, and antituberculosis effects. In this study, the chemical reactivity, electronic, and structural properties of an imidazole-based compound, (E)-4-((2-butyl-5-(2-carboxy-3-(thiophen-2-yl)prop-1-en-1-yl)-1<i>H</i>-imidazol-1-yl)methyl)benzoic acid (Eprosartan), were investigated using DFT methods (PBEPBE and B3LYP) with the 6-31G(d, p) basis set. The most stable molecular conformation was determined through geometry optimization. Key electronic descriptors, including HOMO, LUMO, energy gap, chemical hardness (η), softness (S), ionization potential (I), electron affinity (A), electronegativity (χ), and electrophilicity index (ω) were calculated to assess the molecule’s reactivity. Natural Bond Orbital (NBO) analysis was used to explore intramolecular charge transfer and bonding interactions, while reactive regions were visualized using Molecular Electrostatic Potential (MEP) maps. Nonlinear optical (NLO) properties were evaluated to assess the compound’s potential optoelectronic applications. Mulliken charge analysis provided insights into charge distribution and possible reaction mechanisms. The compound’s low HOMO-LUMO energy gap (0.235&#xa0;eV for PBEPBE and 0.389&#xa0;eV for B3LYP) indicates high reactivity and potential biological activity. Molecular docking studies revealed strong binding affinities with diabetes-related enzymes, namely Protein Tyrosine Phosphatase 1B (4IBM, – 8.30&#xa0;kcal/mol) and Dipeptidyl Peptidase-4 (6FEQ, – 8.70&#xa0;kcal/mol), suggesting potential inhibitory activity. ADMET analyses confirmed favorable drug-likeness and pharmacokinetic properties. These findings collectively indicate that Eprosartan exhibits versatile chemical and biological properties and may serve as a promising candidate for therapeutic development, particularly in the diabetes treatment.</p>

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Chemical reactivity, molecular docking and ADMET profile of (E)-4-((2-butyl-5-(2-carboxy-3-(thiophen-2-yl)prop-1-en-1-yl)-1H-imidazol-1-yl)methyl)benzoic acid molecule: evaluation as a diabetes drug candidate

  • 期刊论文

  • 发表日期：

    2026年1月27日

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  • Efdal Çimen,
  • Kenan Gören,
  • Veysel Tahiroğlu,
  • Mehmet Bağlan

摘要

Imidazole derivatives are important heterocyclic compounds known for their broad pharmacological activities, including antimicrobial, anti-inflammatory, antitumor, analgesic, anti-HIV, and antituberculosis effects. In this study, the chemical reactivity, electronic, and structural properties of an imidazole-based compound, (E)-4-((2-butyl-5-(2-carboxy-3-(thiophen-2-yl)prop-1-en-1-yl)-1H-imidazol-1-yl)methyl)benzoic acid (Eprosartan), were investigated using DFT methods (PBEPBE and B3LYP) with the 6-31G(d, p) basis set. The most stable molecular conformation was determined through geometry optimization. Key electronic descriptors, including HOMO, LUMO, energy gap, chemical hardness (η), softness (S), ionization potential (I), electron affinity (A), electronegativity (χ), and electrophilicity index (ω) were calculated to assess the molecule’s reactivity. Natural Bond Orbital (NBO) analysis was used to explore intramolecular charge transfer and bonding interactions, while reactive regions were visualized using Molecular Electrostatic Potential (MEP) maps. Nonlinear optical (NLO) properties were evaluated to assess the compound’s potential optoelectronic applications. Mulliken charge analysis provided insights into charge distribution and possible reaction mechanisms. The compound’s low HOMO-LUMO energy gap (0.235 eV for PBEPBE and 0.389 eV for B3LYP) indicates high reactivity and potential biological activity. Molecular docking studies revealed strong binding affinities with diabetes-related enzymes, namely Protein Tyrosine Phosphatase 1B (4IBM, – 8.30 kcal/mol) and Dipeptidyl Peptidase-4 (6FEQ, – 8.70 kcal/mol), suggesting potential inhibitory activity. ADMET analyses confirmed favorable drug-likeness and pharmacokinetic properties. These findings collectively indicate that Eprosartan exhibits versatile chemical and biological properties and may serve as a promising candidate for therapeutic development, particularly in the diabetes treatment.