Synthesis and Characterisation of Halogenated Vanillin Derivatives as Potential Antibacterial Agents

The escalating issue of antimicrobial resistance has become a pressing global challenge and poses a significant threat to public health. Thus, new potent drugs derived from natural product are in demand in the pharmaceutical sector as it offers a wide range of chemical structures and diverse bioacti...

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Main Author:	Mohamad Azmeer, Hissam
Format:	Thesis
Language:	English English English
Published:	2024
Subjects:	QD Chemistry QR Microbiology RS Pharmacy and materia medica
Online Access:	http://ir.unimas.my/id/eprint/44668/1/DSVA_Mohamad%20Azmeer.pdf http://ir.unimas.my/id/eprint/44668/2/24pgs%20Mohamad%20Azmeer.pdf http://ir.unimas.my/id/eprint/44668/7/PHD%20Thesis%20Mohamad%20Azmeer.pdf
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spelling	my-unimas-ir.446682024-06-14T09:07:30Z Synthesis and Characterisation of Halogenated Vanillin Derivatives as Potential Antibacterial Agents 2024-09-26 Mohamad Azmeer, Hissam QD Chemistry QR Microbiology RM Therapeutics. Pharmacology RS Pharmacy and materia medica The escalating issue of antimicrobial resistance has become a pressing global challenge and poses a significant threat to public health. Thus, new potent drugs derived from natural product are in demand in the pharmaceutical sector as it offers a wide range of chemical structures and diverse bioactive compounds. However, the extraction of secondary metabolites from natural resources are labour-intensive, time-consuming and frequently inefficient due to the mismatch between the active group and the target receptor. Chemical modification of a lead compound derived from natural resources such as vanillin has garnered increasing attention for pharmacological purposes. In this study, three different series of novel vanillin derivatives namely halogenated vanillin azo derivatives (43a-h) were successfully synthesised via diazo coupling reaction, while halogenated vanillin Schiff base derivatives were prepared via nucleophilic substitution reaction (44a-h). The hybrid molecules of vanillin azo-Schiff base derivatives bearing halogens (Br, Cl, F) (45a-h) were prepared from the reaction of 43a-h with aniline to give significant yields of 67-83% via microwave irradiation method compared to the conventional heating (38-53%). The antibacterial assay of all synthesised compounds at a concentration of 100 ppm was evaluated employing Kirby-Bauer disc diffusion assays against Escherichia coli (ATCC 25922) and Staphylococcus aureus (S48/81). All target compounds were active against both bacterial strains in comparison to the parent vanillin. Compounds 43a-h and 44a-h were active against S. aureus with inhibition zones of 7-10 mm and 8-13 mm, respectively, but less active against E. coli with inhibition zones of 7-9 mm and 7-8 mm, respectively. Notably, compounds 45a-h demonstrated good antibacterial activity (8-11mm) against both bacterial strains in comparison to the standard drug ampicillin (11 mm). Among the halogenated vanillin azo-Schiff base derivatives, compound bearing fluorine at meta position (45b) demonstrated excellent antibacterial efficacy against E. coli and S. aureus with both inhibition zones of 11 mm respectively, comparable to standard drug ampicillin. The successful synthesis of these hybrid vanillin azo-Schiff base derivatives implies their potential utility in drug design that will aid in the development of new, potent antibacterial drugs with excellent properties. Taylor & Francis 2024-09 Thesis http://ir.unimas.my/id/eprint/44668/ http://ir.unimas.my/id/eprint/44668/1/DSVA_Mohamad%20Azmeer.pdf text en staffonly http://ir.unimas.my/id/eprint/44668/2/24pgs%20Mohamad%20Azmeer.pdf text en public http://ir.unimas.my/id/eprint/44668/7/PHD%20Thesis%20Mohamad%20Azmeer.pdf text en validuser masters Universiti Malaysia Sarawak Faculty of Resource Science and Technology
institution	Universiti Malaysia Sarawak
collection	UNIMAS Institutional Repository
language	English English English
topic	QD Chemistry QR Microbiology QD Chemistry RS Pharmacy and materia medica
spellingShingle	QD Chemistry QR Microbiology QD Chemistry RS Pharmacy and materia medica Mohamad Azmeer, Hissam Synthesis and Characterisation of Halogenated Vanillin Derivatives as Potential Antibacterial Agents
description	The escalating issue of antimicrobial resistance has become a pressing global challenge and poses a significant threat to public health. Thus, new potent drugs derived from natural product are in demand in the pharmaceutical sector as it offers a wide range of chemical structures and diverse bioactive compounds. However, the extraction of secondary metabolites from natural resources are labour-intensive, time-consuming and frequently inefficient due to the mismatch between the active group and the target receptor. Chemical modification of a lead compound derived from natural resources such as vanillin has garnered increasing attention for pharmacological purposes. In this study, three different series of novel vanillin derivatives namely halogenated vanillin azo derivatives (43a-h) were successfully synthesised via diazo coupling reaction, while halogenated vanillin Schiff base derivatives were prepared via nucleophilic substitution reaction (44a-h). The hybrid molecules of vanillin azo-Schiff base derivatives bearing halogens (Br, Cl, F) (45a-h) were prepared from the reaction of 43a-h with aniline to give significant yields of 67-83% via microwave irradiation method compared to the conventional heating (38-53%). The antibacterial assay of all synthesised compounds at a concentration of 100 ppm was evaluated employing Kirby-Bauer disc diffusion assays against Escherichia coli (ATCC 25922) and Staphylococcus aureus (S48/81). All target compounds were active against both bacterial strains in comparison to the parent vanillin. Compounds 43a-h and 44a-h were active against S. aureus with inhibition zones of 7-10 mm and 8-13 mm, respectively, but less active against E. coli with inhibition zones of 7-9 mm and 7-8 mm, respectively. Notably, compounds 45a-h demonstrated good antibacterial activity (8-11mm) against both bacterial strains in comparison to the standard drug ampicillin (11 mm). Among the halogenated vanillin azo-Schiff base derivatives, compound bearing fluorine at meta position (45b) demonstrated excellent antibacterial efficacy against E. coli and S. aureus with both inhibition zones of 11 mm respectively, comparable to standard drug ampicillin. The successful synthesis of these hybrid vanillin azo-Schiff base derivatives implies their potential utility in drug design that will aid in the development of new, potent antibacterial drugs with excellent properties.
format	Thesis
qualification_level	Master's degree
author	Mohamad Azmeer, Hissam
author_facet	Mohamad Azmeer, Hissam
author_sort	Mohamad Azmeer, Hissam
title	Synthesis and Characterisation of Halogenated Vanillin Derivatives as Potential Antibacterial Agents
title_short	Synthesis and Characterisation of Halogenated Vanillin Derivatives as Potential Antibacterial Agents
title_full	Synthesis and Characterisation of Halogenated Vanillin Derivatives as Potential Antibacterial Agents
title_fullStr	Synthesis and Characterisation of Halogenated Vanillin Derivatives as Potential Antibacterial Agents
title_full_unstemmed	Synthesis and Characterisation of Halogenated Vanillin Derivatives as Potential Antibacterial Agents
title_sort	synthesis and characterisation of halogenated vanillin derivatives as potential antibacterial agents
granting_institution	Universiti Malaysia Sarawak
granting_department	Faculty of Resource Science and Technology
publishDate	2024
url	http://ir.unimas.my/id/eprint/44668/1/DSVA_Mohamad%20Azmeer.pdf http://ir.unimas.my/id/eprint/44668/2/24pgs%20Mohamad%20Azmeer.pdf http://ir.unimas.my/id/eprint/44668/7/PHD%20Thesis%20Mohamad%20Azmeer.pdf
_version_	1804888432330145792

Synthesis and Characterisation of Halogenated Vanillin Derivatives as Potential Antibacterial Agents

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