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)
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 w...
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my.unimas.ir.447672024-05-16T04:26:23Z http://ir.unimas.my/id/eprint/44767/ 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 Zainab, Ngaini Q Science (General) QD Chemistry 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. Malaysian Analytical Sciences Society (ANALIS) 2023 Article PeerReviewed text en http://ir.unimas.my/id/eprint/44767/1/MICROWAVE-ASSISTED.pdf 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 https://mjas.analis.com.my/mjas/v27_n2/v27_n2.html |
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Q Science (General) QD Chemistry Nur Arif, Mortadza Zainab, Ngaini 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) |
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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. |
format |
Article |
author |
Nur Arif, Mortadza Zainab, Ngaini |
author_facet |
Nur Arif, Mortadza Zainab, Ngaini |
author_sort |
Nur Arif, Mortadza |
title |
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) |
title_short |
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) |
title_full |
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) |
title_fullStr |
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) |
title_full_unstemmed |
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) |
title_sort |
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) |
publisher |
Malaysian Analytical Sciences Society (ANALIS) |
publishDate |
2023 |
url |
http://ir.unimas.my/id/eprint/44767/1/MICROWAVE-ASSISTED.pdf http://ir.unimas.my/id/eprint/44767/ https://mjas.analis.com.my/mjas/v27_n2/v27_n2.html |
_version_ |
1800728098162868224 |
score |
13.18916 |