MICROWAVE-ASSISTED AND CONVENTIONAL SYNTHESIS OF HALOGENATED COUMARIN-AZO DERIVATIVES AND STRUCTURALACTIVITY RELATIONSHIP STUDY FOR ANTIMICROBIAL POTENTIAL = (Sintesis Berbantukan Gelombang Mikro dan Konvensional Derivatif Coumarin-Azo Berhalogen dan Kajian Hubungan Struktur-Aktiviti untuk Potensi Antimikrob)

Nur Arif, Mortadza and Zainab, Ngaini (2023) MICROWAVE-ASSISTED AND CONVENTIONAL SYNTHESIS OF HALOGENATED COUMARIN-AZO DERIVATIVES AND STRUCTURALACTIVITY RELATIONSHIP STUDY FOR ANTIMICROBIAL POTENTIAL = (Sintesis Berbantukan Gelombang Mikro dan Konvensional Derivatif Coumarin-Azo Berhalogen dan Kajian Hubungan Struktur-Aktiviti untuk Potensi Antimikrob). Malaysian Journal of Analytical Sciences, 27 (2). pp. 342-352. ISSN 1394-2506

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Abstract

Untreatable bacterial infectious diseases have become a leading cause of mortality due to the emergence of drug-resistant bacteria. The search for a new effective pharmaceutical drug can be time-consuming and expensive. Therefore, structural chemical modification of natural product-based compounds with known biological properties for potential drug candidates has gained a great interest among researchers. Microwave-assisted synthesis is quickly becoming the method of choice in modern organic synthesis for drug discovery due to benefits such as higher yield and shorter reaction time. In this study, a series of coumarin derivatives have been synthesized by incorporating halogenated azo moieties in the molecular network via diazo-coupling, Knoevenagel condensation, and hydrolysis reactions. Microwave-assisted organic synthesis reaction has produced overall higher yields of products (74-94 %) in 6-17 mins compared to the conventional reflux method (56-85 %) in 6-18 h. The structural activity relationship of all compounds was initially evaluated via in silico (molecular docking) for potential antimicrobial properties against Escherichia coli and Staphylococcus aureus. The synthesized compound gave a higher binding affinity (-6.3 to -8.9 kcal/mol) compared to ampicillin (-6.7 to -7.3 kcal/mol) and coumarin (-6.0 to -6.2 kcal/mol). In vitro evaluation (agar well diffusion), nevertheless, gave weak to no bacterial inhibition activity. This study is significant in searching for potential drug precursors to benefit mankind.

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