Scholarlink

<p>The cycloaddition reaction between cyclopenta-1,3-diene and a mixture of 3-oxo-1-phenylbut-1-en-1-ylium and 4,4,4-trifluoro-3-oxo-1-phenylbut-1-en-1-ylium was investigated using Molecular Electron Density Theory (MEDT), both in the absence and presence of a BF₃ catalyst. This theoretical approach enabled an in-depth examination of the reaction mechanisms, free energy profiles, and stereoselectivity. The reactions favored the formation of specific stereoisomers depending on the catalytic conditions: Product P-2 predominates in the absence of BF₃, while the presence of BF₃ shifts the selectivity toward product P-1. Complementary Electron Localization Function (ELF) and Bonding Evolution Theory (BET) analyses confirmed that both reactions proceed through a non-concerted and asynchronous mechanism, with the formation of the C2–C10 bond preceding that of C3–C12. The presence of the BF₃ catalyst was found to promote a more efficient electron density reorganization, as reflected by earlier and faster development of key bonding interactions. Molecular docking analysis revealed that the incorporation of a CF₃ group significantly enhances the binding affinity of the ligands (P-1 and P-2) to viral proteins, underscoring their potential as antiviral drug candidates. Furthermore, ADMET analysis revealed full compliance with Lipinski’s Rule of Five, favorable molecular weights, excellent predicted gastrointestinal absorption, absence of mutagenic or cardiotoxic effects, and reasonable synthetic accessibility, collectively supporting their suitability as promising oral drug candidates. An adsorption study on silica gel also demonstrated stronger interaction with P-2 due to the CF₃ group, enabling efficient chromatographic separation from P-1.</p>

错误：搜索内容不能为空，请输入英文关键词
错误：关键词超出字数限制，请精简
高级检索

Molecular docking, toxicity assessment and theoretical analysis of the cycloaddition of cyclopenta-1,3-diene with fluorescent enones: catalytic effect and stereoselective implications

  • 期刊论文

  • 发表日期：

    2025年6月28日

查看全文
  • Khadija El Idrissi,
  • Abdellah Zeroual,
  • Ali H. Bahkali,
  • Shifa Wang,
  • Asad Syed,
  • Hocine Garmes

摘要

The cycloaddition reaction between cyclopenta-1,3-diene and a mixture of 3-oxo-1-phenylbut-1-en-1-ylium and 4,4,4-trifluoro-3-oxo-1-phenylbut-1-en-1-ylium was investigated using Molecular Electron Density Theory (MEDT), both in the absence and presence of a BF₃ catalyst. This theoretical approach enabled an in-depth examination of the reaction mechanisms, free energy profiles, and stereoselectivity. The reactions favored the formation of specific stereoisomers depending on the catalytic conditions: Product P-2 predominates in the absence of BF₃, while the presence of BF₃ shifts the selectivity toward product P-1. Complementary Electron Localization Function (ELF) and Bonding Evolution Theory (BET) analyses confirmed that both reactions proceed through a non-concerted and asynchronous mechanism, with the formation of the C2–C10 bond preceding that of C3–C12. The presence of the BF₃ catalyst was found to promote a more efficient electron density reorganization, as reflected by earlier and faster development of key bonding interactions. Molecular docking analysis revealed that the incorporation of a CF₃ group significantly enhances the binding affinity of the ligands (P-1 and P-2) to viral proteins, underscoring their potential as antiviral drug candidates. Furthermore, ADMET analysis revealed full compliance with Lipinski’s Rule of Five, favorable molecular weights, excellent predicted gastrointestinal absorption, absence of mutagenic or cardiotoxic effects, and reasonable synthetic accessibility, collectively supporting their suitability as promising oral drug candidates. An adsorption study on silica gel also demonstrated stronger interaction with P-2 due to the CF₃ group, enabling efficient chromatographic separation from P-1.