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<p>A novel series of disubstituted 1,2,3-triazolo-benzimidazole derivatives (8a-8&#xa0;g) was efficiently synthesized via copper-catalyzed azide-alkyne cycloaddition (CuAAC) under ultrasonic irradiation, achieving up to 95% yields in 55&#xa0;min at room temperature. This green sonochemical protocol significantly outperformed conventional methods, yielding high-purity products, as confirmed by FT-IR, <sup>1</sup>H/<sup>13</sup>C NMR, and Mass spectrometry. In vitro antimicrobial assays revealed potent activity against Gram-positive (<i>S. aureus</i>,<i> B. cereus</i>) and Gram-negative (<i>S. typhimurium</i>,<i> E. coli</i>) strains, with compounds <b>8a</b>, <b>8c</b> and <b>8d</b> outperforming tetracycline in several cases (zones up to 29&#xa0;mm). Molecular docking against the Cro repressor (PDB: 1LMB) showed strong binding affinities (-5.07 to -5.67&#xa0;kcal/mol), with <b>8a</b> forming key H-bonds to DC29 and hydrophobic contacts to DG14. In silico ADME profiling confirmed drug-likeness (no Lipinski violations, bioavailability score 0.55) and low toxicity, whereas DFT analysis highlighted the high reactivity of <b>8c</b> (ΔE<sub>gap</sub> = 1.998&#xa0;eV). SAR studies underscored the role of 2,4-dimethyl/dinitro substitutions in enhancing broad-spectrum potency, positioning these hybrids as promising antimicrobial leads.</p> Graphical Abstract <p></p>

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Computational design and sonochemical synthesis of triazolo benzimidazole derivatives as an antimicrobial agent

  • 期刊论文

  • 出版模式：

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  • 发表日期：

    2026年5月11日

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  • Priyank M. Shah,
  • Anjalee R. Khoyanee,
  • Kalpna Rakholiya,
  • Mital Kaneria,
  • Ranjan C. Khunt

摘要

A novel series of disubstituted 1,2,3-triazolo-benzimidazole derivatives (8a-8 g) was efficiently synthesized via copper-catalyzed azide-alkyne cycloaddition (CuAAC) under ultrasonic irradiation, achieving up to 95% yields in 55 min at room temperature. This green sonochemical protocol significantly outperformed conventional methods, yielding high-purity products, as confirmed by FT-IR, 1H/13C NMR, and Mass spectrometry. In vitro antimicrobial assays revealed potent activity against Gram-positive (S. aureus, B. cereus) and Gram-negative (S. typhimurium, E. coli) strains, with compounds 8a, 8c and 8d outperforming tetracycline in several cases (zones up to 29 mm). Molecular docking against the Cro repressor (PDB: 1LMB) showed strong binding affinities (-5.07 to -5.67 kcal/mol), with 8a forming key H-bonds to DC29 and hydrophobic contacts to DG14. In silico ADME profiling confirmed drug-likeness (no Lipinski violations, bioavailability score 0.55) and low toxicity, whereas DFT analysis highlighted the high reactivity of 8c (ΔEgap = 1.998 eV). SAR studies underscored the role of 2,4-dimethyl/dinitro substitutions in enhancing broad-spectrum potency, positioning these hybrids as promising antimicrobial leads.

Graphical Abstract