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<p>An efficient and eco-friendly method was developed for synthesizing coumarin–thiazolidinone hybrids using choline hydroxide as a green catalyst. A series of arylidene derivatives (<b>3a–i, 5</b>) were prepared and characterized. Antimicrobial screening against Gram-positive and Gram-negative bacteria, yeast, and fungi demonstrated significant activity, particularly for compound <b>3c</b>, which produced inhibition zones of up to 30.8 mm against <i>Staphylococcus aureus</i>, and compound <b>3i</b>, which showed a MIC of 6.25 µg/mL against <i>Escherichia coli</i>, comparable to standard antibiotics. Structure–activity relationship analysis revealed that electron-donating substituents (–OCH₃, indolyl) markedly enhanced potency, while halogen and nitro substituents reduced activity. DFT calculations supported these findings, with <b>3i</b> showing a low HOMO–LUMO gap (3.183 eV) indicating high reactivity. Molecular docking against Staphylococcus aureus dihydrofolate reductase (PDB: 2XCT) confirmed strong binding, with compound <b>3c</b> achieving a docking score of –8.6 kcal/mol. These results establish coumarin–thiazolidinone hybrids as promising scaffolds for antimicrobial drug development.</p>

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Choline hydroxide mediated eco-friendly synthesis of 5-arylidene thiazol-4(5H)-one clubbed coumarin: antimicrobial evaluation and in silico studies

  • 期刊论文

  • 发表日期：

    2025年10月1日

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  • Muneera S. M. Al-Saleem,
  • Jehan Y. Al-Humaidi,
  • Ahmed A. Elhenawy,
  • Sayed M. Riyadh,
  • Magdi E. A. Zaki,
  • Ohoud A. Jefri,
  • Sobhi M. Gomha

摘要

An efficient and eco-friendly method was developed for synthesizing coumarin–thiazolidinone hybrids using choline hydroxide as a green catalyst. A series of arylidene derivatives (3a–i, 5) were prepared and characterized. Antimicrobial screening against Gram-positive and Gram-negative bacteria, yeast, and fungi demonstrated significant activity, particularly for compound 3c, which produced inhibition zones of up to 30.8 mm against Staphylococcus aureus, and compound 3i, which showed a MIC of 6.25 µg/mL against Escherichia coli, comparable to standard antibiotics. Structure–activity relationship analysis revealed that electron-donating substituents (–OCH₃, indolyl) markedly enhanced potency, while halogen and nitro substituents reduced activity. DFT calculations supported these findings, with 3i showing a low HOMO–LUMO gap (3.183 eV) indicating high reactivity. Molecular docking against Staphylococcus aureus dihydrofolate reductase (PDB: 2XCT) confirmed strong binding, with compound 3c achieving a docking score of –8.6 kcal/mol. These results establish coumarin–thiazolidinone hybrids as promising scaffolds for antimicrobial drug development.