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Abstract <p>The use of antibiotics is causing rapid growth of antibiotic-resistant bacteria. This can result in significant challenges for controlling pathogenic diseases in the future. The search for new potential antimicrobial compounds is critical, and natural-based scaffolds such as coumarin offer promising lead compounds for the development of new antibacterial compounds through structural hybridization. This study aims to synthesize coumarin–triazene–alkoxyphenyl hybrids <b>4a</b>–<b>4c</b> bearing a long alkoxy chain and evaluate their antimicrobial potential via docking simulation. The synthesis started with the preparation of alkoxyanilines <b>2a</b>–<b>2c</b> and cyanocoumarin <b>3</b> as precursors under microwave irradiation, resulting in a better yield (68–82 and 61%, respectively) in a few minutes. Diazo coupling reaction of <b>2a–2c</b> and <b>3</b> produced coumarin–triazene hybrids <b>4a</b>–<b>4c</b> with 47–63% yield. In silico simulation showed that compound <b>4a</b> had a binding affinity (–6.7 kcal/mol) toward bacterial DNA gyrase similar to clorobiocin as reference compound, which indicates its potential to influence and inhibit the activity of the bacterial enzyme. These preliminary findings could establish a useful basis for discovering new antimicrobial compounds through derivatization or modification of the coumarin scaffold.</p>

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Synthesis of Coumarin–Triazene–Alkoxyphenyl Derivatives and In Silico Simulation for Potential Antimicrobial Activity

  • 期刊论文

  • 发表日期：

    2025年1月1日

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  • N. A. Mortadza,
  • E. Madiahlagan,
  • Z. Ngaini

摘要

Abstract

The use of antibiotics is causing rapid growth of antibiotic-resistant bacteria. This can result in significant challenges for controlling pathogenic diseases in the future. The search for new potential antimicrobial compounds is critical, and natural-based scaffolds such as coumarin offer promising lead compounds for the development of new antibacterial compounds through structural hybridization. This study aims to synthesize coumarin–triazene–alkoxyphenyl hybrids 4a–4c bearing a long alkoxy chain and evaluate their antimicrobial potential via docking simulation. The synthesis started with the preparation of alkoxyanilines 2a–2c and cyanocoumarin 3 as precursors under microwave irradiation, resulting in a better yield (68–82 and 61%, respectively) in a few minutes. Diazo coupling reaction of 2a–2c and 3 produced coumarin–triazene hybrids 4a–4c with 47–63% yield. In silico simulation showed that compound 4a had a binding affinity (–6.7 kcal/mol) toward bacterial DNA gyrase similar to clorobiocin as reference compound, which indicates its potential to influence and inhibit the activity of the bacterial enzyme. These preliminary findings could establish a useful basis for discovering new antimicrobial compounds through derivatization or modification of the coumarin scaffold.