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<p>The compound 1-(piperazin-1-yl)-2-(thiophen-2-yl) ethan-1-one (<b>PT</b>) was comprehensively investigated through computational and molecular docking approaches to evaluate its structural, electronic, and pharmacological properties. Density functional theory (DFT) calculations at the B3LYP/cc-pVDZ level were employed to optimize molecular geometry and analyze electronic descriptors, including frontier molecular orbitals (FMOs), global reactivity parameters, and dipole moments in both gas and solvent phases. <b>PT</b> demonstrated moderate chemical stability, high nucleophilicity, and low electrophilicity, suggesting potential for biological activity. Non-linear optical (NLO) properties and UV-spectra computed via time-dependent DFT (TD-DFT) revealed strong solvent dependence and enhanced polarizability, particularly in polar environments. Molecular electrostatic potential (MEP), electron localization function (ELF), and localized orbital locator (LOL) analyses provided deeper insights into reactive sites and electron distribution. Furthermore, natural population analysis (NPA), Mulliken charge distribution, and natural bond orbital (NBO) analyses confirmed intramolecular charge delocalization and stabilizing donor–acceptor interactions. Finally, molecular docking simulations revealed favorable binding of <b>PT</b> to the human SGLT2-MAP17 protein complex (PDB ID: 8HEZ), with a binding energy of −6.93&#xa0;kcal/mol and multiple stabilizing noncovalent interactions. These findings suggest that <b>PT</b> could serve as a promising lead compound for SGLT2 inhibition and warrant further pharmacological evaluation.</p>

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Piperazine-thiophene hybrid as a promising SGLT2 inhibitor: insights from DFT and molecular docking studies

  • 期刊论文

  • 发表日期：

    2025年7月5日

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  • Özlem Gündoğdu Aytaç,
  • Abdurrahman Atalay,
  • Ebrar Nur Özkan,
  • Sertan Aytaç

摘要

The compound 1-(piperazin-1-yl)-2-(thiophen-2-yl) ethan-1-one (PT) was comprehensively investigated through computational and molecular docking approaches to evaluate its structural, electronic, and pharmacological properties. Density functional theory (DFT) calculations at the B3LYP/cc-pVDZ level were employed to optimize molecular geometry and analyze electronic descriptors, including frontier molecular orbitals (FMOs), global reactivity parameters, and dipole moments in both gas and solvent phases. PT demonstrated moderate chemical stability, high nucleophilicity, and low electrophilicity, suggesting potential for biological activity. Non-linear optical (NLO) properties and UV-spectra computed via time-dependent DFT (TD-DFT) revealed strong solvent dependence and enhanced polarizability, particularly in polar environments. Molecular electrostatic potential (MEP), electron localization function (ELF), and localized orbital locator (LOL) analyses provided deeper insights into reactive sites and electron distribution. Furthermore, natural population analysis (NPA), Mulliken charge distribution, and natural bond orbital (NBO) analyses confirmed intramolecular charge delocalization and stabilizing donor–acceptor interactions. Finally, molecular docking simulations revealed favorable binding of PT to the human SGLT2-MAP17 protein complex (PDB ID: 8HEZ), with a binding energy of −6.93 kcal/mol and multiple stabilizing noncovalent interactions. These findings suggest that PT could serve as a promising lead compound for SGLT2 inhibition and warrant further pharmacological evaluation.