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Synthesis and Biological Activities of Mono Aspirinate Thiourea-Azo Derivatives

The emergence of bacterial resistance diseases has triggered researchers to search for a precursor derived from natural product-based molecules. Modification of natural product-based molecules such as aspirin has been extensively studied for pharmacological purposes. In this study, a series of new h...

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Main Author: Ferlicia, Rasin
Format: Thesis
Language:English
Published: Universiti Malaysia Sarawak (UNIMAS) 2021
Subjects:
Q Science (General)
QD Chemistry
Online Access:http://ir.unimas.my/id/eprint/36831/5/Ferlicia.pdf
http://ir.unimas.my/id/eprint/36831/
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spelling my.unimas.ir-368312024-11-11T02:25:54Z http://ir.unimas.my/id/eprint/36831/ Synthesis and Biological Activities of Mono Aspirinate Thiourea-Azo Derivatives Ferlicia, Rasin Q Science (General) QD Chemistry The emergence of bacterial resistance diseases has triggered researchers to search for a precursor derived from natural product-based molecules. Modification of natural product-based molecules such as aspirin has been extensively studied for pharmacological purposes. In this study, a series of new halogenated azo derivatives (55a-i, 56a-i) and mono aspirinate thiourea-azo derivatives (57a-i) have been successfully synthesised using aspirin as a precursor. Halogenated azo derivatives precursors (55a-i) were prepared via coupling reaction of 4-acetamidophenol with commercially available halogenated aniline derivatives with 14-37% yield while aspirinate thiourea-azo derivatives (57a-i) were synthesised via nucleophilic substitution reaction of acetoxybenzoyl isothiocyanate intermediate with synthesised halogenated amine derivatives (56a-i) with 70-90% yield. The structures of all the synthesised compounds were analysed using elemental analysis (CHNS) and characterised via Nuclear Magnetic Resonance (1H and 13C NMR) and Fourier Transform Infrared (FTIR) spectroscopy which correspond to the synthesised compounds. All compounds with concentration of 10 mg/mL were evaluated for antibacterial activities against Escherichia coli (ATCC 25922) and Staphylococcus aureus (S48/81) via disc diffusion assay. Halogenated azo derivatives series (55a-i, 56a-i) showed no inhibition against both bacteria strains. Interestingly, the aspirinate thiourea-azo derivatives (57a-i) showed good antibacterial activity against S. aureus and no inhibition against E. coli. Among all the aspirinate thiourea-azo derivatives (57a-i), only 2-(((3-((2-bromophenyl)diazenyl)-4-hydroxyphenyl)carbamothioyl) carbamoyl)phenyl acetate (57g) showed excellent antibacterial activity with a larger zone of inhibition (10 mm) and comparable to the standard drug, ampicillin. The synthesised hybrid aspirinate thiourea-azo derivatives has the potential in pharmaceutical industries as new drugs with the bacteriostatic property. Universiti Malaysia Sarawak (UNIMAS) 2021 Thesis NonPeerReviewed text en http://ir.unimas.my/id/eprint/36831/5/Ferlicia.pdf Ferlicia, Rasin (2021) Synthesis and Biological Activities of Mono Aspirinate Thiourea-Azo Derivatives. Masters thesis, Universiti Malaysia Sarawak.
institution Universiti Malaysia Sarawak
building Centre for Academic Information Services (CAIS)
collection Institutional Repository
continent Asia
country Malaysia
content_provider Universiti Malaysia Sarawak
content_source UNIMAS Institutional Repository
url_provider http://ir.unimas.my/
language English
topic Q Science (General)
QD Chemistry
spellingShingle Q Science (General)
QD Chemistry
Ferlicia, Rasin
Synthesis and Biological Activities of Mono Aspirinate Thiourea-Azo Derivatives
description The emergence of bacterial resistance diseases has triggered researchers to search for a precursor derived from natural product-based molecules. Modification of natural product-based molecules such as aspirin has been extensively studied for pharmacological purposes. In this study, a series of new halogenated azo derivatives (55a-i, 56a-i) and mono aspirinate thiourea-azo derivatives (57a-i) have been successfully synthesised using aspirin as a precursor. Halogenated azo derivatives precursors (55a-i) were prepared via coupling reaction of 4-acetamidophenol with commercially available halogenated aniline derivatives with 14-37% yield while aspirinate thiourea-azo derivatives (57a-i) were synthesised via nucleophilic substitution reaction of acetoxybenzoyl isothiocyanate intermediate with synthesised halogenated amine derivatives (56a-i) with 70-90% yield. The structures of all the synthesised compounds were analysed using elemental analysis (CHNS) and characterised via Nuclear Magnetic Resonance (1H and 13C NMR) and Fourier Transform Infrared (FTIR) spectroscopy which correspond to the synthesised compounds. All compounds with concentration of 10 mg/mL were evaluated for antibacterial activities against Escherichia coli (ATCC 25922) and Staphylococcus aureus (S48/81) via disc diffusion assay. Halogenated azo derivatives series (55a-i, 56a-i) showed no inhibition against both bacteria strains. Interestingly, the aspirinate thiourea-azo derivatives (57a-i) showed good antibacterial activity against S. aureus and no inhibition against E. coli. Among all the aspirinate thiourea-azo derivatives (57a-i), only 2-(((3-((2-bromophenyl)diazenyl)-4-hydroxyphenyl)carbamothioyl) carbamoyl)phenyl acetate (57g) showed excellent antibacterial activity with a larger zone of inhibition (10 mm) and comparable to the standard drug, ampicillin. The synthesised hybrid aspirinate thiourea-azo derivatives has the potential in pharmaceutical industries as new drugs with the bacteriostatic property.
format Thesis
author Ferlicia, Rasin
author_facet Ferlicia, Rasin
author_sort Ferlicia, Rasin
title Synthesis and Biological Activities of Mono Aspirinate Thiourea-Azo Derivatives
title_short Synthesis and Biological Activities of Mono Aspirinate Thiourea-Azo Derivatives
title_full Synthesis and Biological Activities of Mono Aspirinate Thiourea-Azo Derivatives
title_fullStr Synthesis and Biological Activities of Mono Aspirinate Thiourea-Azo Derivatives
title_full_unstemmed Synthesis and Biological Activities of Mono Aspirinate Thiourea-Azo Derivatives
title_sort synthesis and biological activities of mono aspirinate thiourea-azo derivatives
publisher Universiti Malaysia Sarawak (UNIMAS)
publishDate 2021
url http://ir.unimas.my/id/eprint/36831/5/Ferlicia.pdf
http://ir.unimas.my/id/eprint/36831/
_version_ 1817848720006316032
score 13.222552

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