Synthesis and Characterization of Triazene and Thiourea Derivatives as Potential Antibacterial Agents

Two different series of triazene 43a-i and thiourea derivatives 45a-i bearing acetanilide moiety with a total of 18 compounds have been successfully synthesized from 4’-aminoacetanilide as the core structure through azo coupling and nucleophilic substitution reaction, respectively. The structures we...

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Main Author:	AINA SYAKIRAH, MOHAMMAD HUSSIN
Format:	Thesis
Language:	English
Published:	2024
Subjects:	QD Chemistry
Online Access:	http://ir.unimas.my/id/eprint/46137/3/Thesis%20Master_Aina%20Syakirah.restricted_restricted.pdf
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spelling	my-unimas-ir.461372024-11-12T00:43:57Z Synthesis and Characterization of Triazene and Thiourea Derivatives as Potential Antibacterial Agents 2024-06-27 AINA SYAKIRAH, MOHAMMAD HUSSIN QD Chemistry Two different series of triazene 43a-i and thiourea derivatives 45a-i bearing acetanilide moiety with a total of 18 compounds have been successfully synthesized from 4’-aminoacetanilide as the core structure through azo coupling and nucleophilic substitution reaction, respectively. The structures were characterized by using Fourier-transform infrared (FTIR) spectroscopy, 1H and 13C nuclear magnetic resonance (NMR) analysis. The unexpected structural formation of 43a-i instead of the initially proposed azo derivatives 42a-i was confirmed by employing correlation spectroscopy (COSY). The antibacterial activity of 43a-i and 45a-i was tested against two types of bacteria which were Staphylococcus aureus (ATCC 25923), a Gram-positive bacterium and Escherichia coli (ATCC 25922), a Gram-negative bacterium. The antibacterial potential was utilized via turbidimetric kinetic method for 43a-i and Kirby-Bauer disc diffusion method for 45a-i. The study revealed that among the triazene series 43a-i, 43c bearing fluorine at para position was the most potent inhibitor against both bacteria with minimum inhibitory concentration (MIC) values of 68 ppm (S. aureus) and 84 ppm (E. coli), surpassing the standard ampicillin with the MIC values of 85 ppm (S. aureus) and 86 ppm (E. coli). The more nitrogen atoms on the triazene bridge along with the fluorine substituent were envisaged to promote greater hydrogen bond interactions with the bacterial receptors. On the other hand, another derivative of the 4’-aminoacetanilide called thiourea derivatives 45a-i showed susceptible inhibition against those bacteria, particularly 45a and 45f with 7-8 mm of inhibition zone, comparable to the standard ampicillin. The similar aspect these compounds possessed was the low molecular weight which resulted in better bacterial membrane penetration. Universiti Malaysia Sarawak 2024-06 Thesis http://ir.unimas.my/id/eprint/46137/ http://ir.unimas.my/id/eprint/46137/3/Thesis%20Master_Aina%20Syakirah.restricted_restricted.pdf text en validuser masters Universiti Malaysia Sarawak Chemistry
institution	Universiti Malaysia Sarawak
collection	UNIMAS Institutional Repository
language	English
topic	QD Chemistry
spellingShingle	QD Chemistry AINA SYAKIRAH, MOHAMMAD HUSSIN Synthesis and Characterization of Triazene and Thiourea Derivatives as Potential Antibacterial Agents
description	Two different series of triazene 43a-i and thiourea derivatives 45a-i bearing acetanilide moiety with a total of 18 compounds have been successfully synthesized from 4’-aminoacetanilide as the core structure through azo coupling and nucleophilic substitution reaction, respectively. The structures were characterized by using Fourier-transform infrared (FTIR) spectroscopy, 1H and 13C nuclear magnetic resonance (NMR) analysis. The unexpected structural formation of 43a-i instead of the initially proposed azo derivatives 42a-i was confirmed by employing correlation spectroscopy (COSY). The antibacterial activity of 43a-i and 45a-i was tested against two types of bacteria which were Staphylococcus aureus (ATCC 25923), a Gram-positive bacterium and Escherichia coli (ATCC 25922), a Gram-negative bacterium. The antibacterial potential was utilized via turbidimetric kinetic method for 43a-i and Kirby-Bauer disc diffusion method for 45a-i. The study revealed that among the triazene series 43a-i, 43c bearing fluorine at para position was the most potent inhibitor against both bacteria with minimum inhibitory concentration (MIC) values of 68 ppm (S. aureus) and 84 ppm (E. coli), surpassing the standard ampicillin with the MIC values of 85 ppm (S. aureus) and 86 ppm (E. coli). The more nitrogen atoms on the triazene bridge along with the fluorine substituent were envisaged to promote greater hydrogen bond interactions with the bacterial receptors. On the other hand, another derivative of the 4’-aminoacetanilide called thiourea derivatives 45a-i showed susceptible inhibition against those bacteria, particularly 45a and 45f with 7-8 mm of inhibition zone, comparable to the standard ampicillin. The similar aspect these compounds possessed was the low molecular weight which resulted in better bacterial membrane penetration.
format	Thesis
qualification_level	Master's degree
author	AINA SYAKIRAH, MOHAMMAD HUSSIN
author_facet	AINA SYAKIRAH, MOHAMMAD HUSSIN
author_sort	AINA SYAKIRAH, MOHAMMAD HUSSIN
title	Synthesis and Characterization of Triazene and Thiourea Derivatives as Potential Antibacterial Agents
title_short	Synthesis and Characterization of Triazene and Thiourea Derivatives as Potential Antibacterial Agents
title_full	Synthesis and Characterization of Triazene and Thiourea Derivatives as Potential Antibacterial Agents
title_fullStr	Synthesis and Characterization of Triazene and Thiourea Derivatives as Potential Antibacterial Agents
title_full_unstemmed	Synthesis and Characterization of Triazene and Thiourea Derivatives as Potential Antibacterial Agents
title_sort	synthesis and characterization of triazene and thiourea derivatives as potential antibacterial agents
granting_institution	Universiti Malaysia Sarawak
granting_department	Chemistry
publishDate	2024
url	http://ir.unimas.my/id/eprint/46137/3/Thesis%20Master_Aina%20Syakirah.restricted_restricted.pdf
_version_	1818611689348661248

Synthesis and Characterization of Triazene and Thiourea Derivatives as Potential Antibacterial Agents

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