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<p>This study presents a two-step protocol for synthesizing 1,4-disubstituted 1,2,3-triazoles. Initially, 1,2,3-triazoles are prepared via a click reaction between phenacyl azide derivatives and aliphatic/aromatic propargyl alcohols, catalyzed by Cu(OAc)<sub>2</sub> in CH<sub>3</sub>CN at 80 °C. Subsequently, two compounds underwent coupling reactions with terminal alkynes or boronic acids, catalyzed by palladium, yielding new 1,4-disubstituted 1,2,3-triazoles. The antibacterial properties of all newly synthesized compounds were tested in vitro against the bacterial strains <i>Staphylococcus aureus</i> and <i>Pseudomonas aeruginosa</i>. One compound exhibited significantly greater activity against <i>S. aureus</i> with a minimum inhibitory concentration (MIC) of 3.12 mg/cm<sup>3</sup>, compared to the standard, which has an MIC of 12.5 mg/cm<sup>3</sup>. The other compounds displayed similar activity to the standard against <i>S. aureus</i> with an MIC of 12.5 mg/cm<sup>3</sup>. Additionally, most compounds demonstrated a MIC of 6.25 mg/cm<sup>3</sup> against <i>P. aeruginosa</i>, similar to the standard.</p> Graphical abstract <p></p>

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Click-coupling synthesis of new 1-phenacyl-4-substituted 1,2,3-triazoles

  • 期刊论文

  • 发表日期：

    2025年4月23日

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  • Saloomeh Maleki,
  • Mohammad Bakherad,
  • Hossein Nasr-Isfahani,
  • Esmaiel Dehghanibavani,
  • Leila Kamrani Tamardash

摘要

This study presents a two-step protocol for synthesizing 1,4-disubstituted 1,2,3-triazoles. Initially, 1,2,3-triazoles are prepared via a click reaction between phenacyl azide derivatives and aliphatic/aromatic propargyl alcohols, catalyzed by Cu(OAc)2 in CH3CN at 80 °C. Subsequently, two compounds underwent coupling reactions with terminal alkynes or boronic acids, catalyzed by palladium, yielding new 1,4-disubstituted 1,2,3-triazoles. The antibacterial properties of all newly synthesized compounds were tested in vitro against the bacterial strains Staphylococcus aureus and Pseudomonas aeruginosa. One compound exhibited significantly greater activity against S. aureus with a minimum inhibitory concentration (MIC) of 3.12 mg/cm3, compared to the standard, which has an MIC of 12.5 mg/cm3. The other compounds displayed similar activity to the standard against S. aureus with an MIC of 12.5 mg/cm3. Additionally, most compounds demonstrated a MIC of 6.25 mg/cm3 against P. aeruginosa, similar to the standard.

Graphical abstract