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

Nur Arif, Mortadza and Eswaran, Madiahlagan and Zainab, Ngaini (2025) Synthesis of Coumarin–Triazene–Alkoxyphenyl Derivatives and In Silico Simulation for Potential Antimicrobial Activity. Russian Journal of Organic Chemistry, 61 (1). pp. 124-132. ISSN 1608-3393

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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

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