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Abstract <p>The rational design of bioactive molecules is greatly accelerated by computational approaches such as molecular docking, which provide crucial predictions of binding affinity and chemical reactivity. This study aligns with this approach by exploiting these methods to predict the key properties of a novel biphenyl derivative. A combined structural characterization and theoretical investigation using density functional theory (DFT) and molecular docking were performed to predict the structural parameters, chemical reactivity, and biological activity of the compound 4,4'-dibromo-2,5-dimethoxy-[1,1-biphenyl]-2,5-dione. In terms of chemical reactivity, the lower energetic gap and higher electrophilicity index indicate that the studied compound is more chemically reactive and possesses significant electrophilic power. The <i>in-silico</i> study conducted using AutoDock Vina showed strong binding affinity between the compound and two proteins: dihydroxyacetanilide epoxidase (PDB ID: 2BNM) and dehydrogenase (PDB ID: 4XD2)<b>,</b> with binding energies of –7.4 and –7.3 kcal/mol, respectively. Hirshfeld surface analysis was performed to evaluate the intermolecular interactions stabilizing the crystal structure. The results revealed that the primary contributors were O···H/H···O (27.7%), Br···H/H···Br (23.2%), and H···H (13.9%) interactions. These findings establish the compound as a promising candidate for the targeted enzymes and reveal key structural features governing its reactivity and binding. This provides a clear rationale for future medicinal chemistry efforts aimed at developing more potent inhibitors, demonstrating the practical value of combined DFT and docking studies in rational drug design.</p>

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Computational and Crystallographic Insights into 4,4'-Dibromo-2,5-dimethoxy-[1,1'-biphenyl]-2,5'-dione: DFT, Hirshfeld Surface, and Molecular Docking Studies

  • 期刊论文

  • 发表日期：

    2025年12月1日

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  • Khayra Hammou,
  • Mohammed Cherif Terkhi,
  • Mansour Azayez,
  • Zohra Douaa Benyahlou,
  • Nourdine Boukabcha,
  • Youcef Megrouss,
  • Mohammed Hadj Mortada Belhachemi,
  • Abdelkader Chouaih

摘要

Abstract

The rational design of bioactive molecules is greatly accelerated by computational approaches such as molecular docking, which provide crucial predictions of binding affinity and chemical reactivity. This study aligns with this approach by exploiting these methods to predict the key properties of a novel biphenyl derivative. A combined structural characterization and theoretical investigation using density functional theory (DFT) and molecular docking were performed to predict the structural parameters, chemical reactivity, and biological activity of the compound 4,4'-dibromo-2,5-dimethoxy-[1,1-biphenyl]-2,5-dione. In terms of chemical reactivity, the lower energetic gap and higher electrophilicity index indicate that the studied compound is more chemically reactive and possesses significant electrophilic power. The in-silico study conducted using AutoDock Vina showed strong binding affinity between the compound and two proteins: dihydroxyacetanilide epoxidase (PDB ID: 2BNM) and dehydrogenase (PDB ID: 4XD2), with binding energies of –7.4 and –7.3 kcal/mol, respectively. Hirshfeld surface analysis was performed to evaluate the intermolecular interactions stabilizing the crystal structure. The results revealed that the primary contributors were O···H/H···O (27.7%), Br···H/H···Br (23.2%), and H···H (13.9%) interactions. These findings establish the compound as a promising candidate for the targeted enzymes and reveal key structural features governing its reactivity and binding. This provides a clear rationale for future medicinal chemistry efforts aimed at developing more potent inhibitors, demonstrating the practical value of combined DFT and docking studies in rational drug design.