Synthesis, characteristic fragmentation patterns, and antibacterial activity of new azo compounds from the coupling reaction of diazobenzothiazole ions and acetaminophen

In this study, a series of azobenzothiazole dyes 4 were synthesized via diazotization of substituted benzothiazole derivatives followed by azo coupling with acetaminophen. The chemical structures of all synthesized compounds were confirmed using analytical data and spectroscopic techniques, includin...

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Autores principales:	Tsemeugne Joseph, Nangmo Pamela Kemda, Mkounga Pierre, Tamokou Jean De Dieu, Kengne Iréne Chinda, Edwards Giles, Sopbué Emmanuel Fondjo, Nkengfack Augustin Ephrem
Formato:	article
Lenguaje:	EN
Publicado:	De Gruyter 2021
Materias:	benzothiazole acetaminophen azo dyes fragmentations antibacterial studies Organic chemistry QD241-441
Acceso en línea:	https://doaj.org/article/a424b438e3fb4995b7554e74f2442895
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spelling	oai:doaj.org-article:a424b438e3fb4995b7554e74f24428952021-12-05T14:10:50ZSynthesis, characteristic fragmentation patterns, and antibacterial activity of new azo compounds from the coupling reaction of diazobenzothiazole ions and acetaminophen2191-019710.1515/hc-2020-0127https://doaj.org/article/a424b438e3fb4995b7554e74f24428952021-10-01T00:00:00Zhttps://doi.org/10.1515/hc-2020-0127https://doaj.org/toc/2191-0197In this study, a series of azobenzothiazole dyes 4 were synthesized via diazotization of substituted benzothiazole derivatives followed by azo coupling with acetaminophen. The chemical structures of all synthesized compounds were confirmed using analytical data and spectroscopic techniques, including UV-visible, IR, mass spectra, and 1H- and 13C-NMR. The in situ formed diazobenzothiazole ions regiospecifically react with acetaminophen derivatives in the Hollemann-guided electrophilic aromatic substitution mechanism. The regio-orientations were established, on the one hand, by a rigorous interpretation of 1H-NMR spectra and, on the other hand, by the characteristic fragmentation patterns observed on the electrospray mass spectra. In the cases of 4a and 4b, multisubstitutions occurred. The antimicrobial activity of compound 4, along with all the starting materials, was investigated on Pseudomonas aeruginosa PA01, Staphylococcus aureus 18, Escherichia coli 64R, and S. aureus ATCC 25923. The results showed that this skeletal framework exhibited marked potency as antibacterial agents. The most active antibacterial agent against both targeted organisms was compound 4a′.Tsemeugne JosephNangmo Pamela KemdaMkounga PierreTamokou Jean De DieuKengne Iréne ChindaEdwards GilesSopbué Emmanuel FondjoNkengfack Augustin EphremDe Gruyterarticlebenzothiazoleacetaminophenazo dyesfragmentationsantibacterial studiesOrganic chemistryQD241-441ENHeterocyclic Communications, Vol 27, Iss 1, Pp 79-89 (2021)
institution	DOAJ
collection	DOAJ
language	EN
topic	benzothiazole acetaminophen azo dyes fragmentations antibacterial studies Organic chemistry QD241-441
spellingShingle	benzothiazole acetaminophen azo dyes fragmentations antibacterial studies Organic chemistry QD241-441 Tsemeugne Joseph Nangmo Pamela Kemda Mkounga Pierre Tamokou Jean De Dieu Kengne Iréne Chinda Edwards Giles Sopbué Emmanuel Fondjo Nkengfack Augustin Ephrem Synthesis, characteristic fragmentation patterns, and antibacterial activity of new azo compounds from the coupling reaction of diazobenzothiazole ions and acetaminophen
description	In this study, a series of azobenzothiazole dyes 4 were synthesized via diazotization of substituted benzothiazole derivatives followed by azo coupling with acetaminophen. The chemical structures of all synthesized compounds were confirmed using analytical data and spectroscopic techniques, including UV-visible, IR, mass spectra, and 1H- and 13C-NMR. The in situ formed diazobenzothiazole ions regiospecifically react with acetaminophen derivatives in the Hollemann-guided electrophilic aromatic substitution mechanism. The regio-orientations were established, on the one hand, by a rigorous interpretation of 1H-NMR spectra and, on the other hand, by the characteristic fragmentation patterns observed on the electrospray mass spectra. In the cases of 4a and 4b, multisubstitutions occurred. The antimicrobial activity of compound 4, along with all the starting materials, was investigated on Pseudomonas aeruginosa PA01, Staphylococcus aureus 18, Escherichia coli 64R, and S. aureus ATCC 25923. The results showed that this skeletal framework exhibited marked potency as antibacterial agents. The most active antibacterial agent against both targeted organisms was compound 4a′.
format	article
author	Tsemeugne Joseph Nangmo Pamela Kemda Mkounga Pierre Tamokou Jean De Dieu Kengne Iréne Chinda Edwards Giles Sopbué Emmanuel Fondjo Nkengfack Augustin Ephrem
author_facet	Tsemeugne Joseph Nangmo Pamela Kemda Mkounga Pierre Tamokou Jean De Dieu Kengne Iréne Chinda Edwards Giles Sopbué Emmanuel Fondjo Nkengfack Augustin Ephrem
author_sort	Tsemeugne Joseph
title	Synthesis, characteristic fragmentation patterns, and antibacterial activity of new azo compounds from the coupling reaction of diazobenzothiazole ions and acetaminophen
title_short	Synthesis, characteristic fragmentation patterns, and antibacterial activity of new azo compounds from the coupling reaction of diazobenzothiazole ions and acetaminophen
title_full	Synthesis, characteristic fragmentation patterns, and antibacterial activity of new azo compounds from the coupling reaction of diazobenzothiazole ions and acetaminophen
title_fullStr	Synthesis, characteristic fragmentation patterns, and antibacterial activity of new azo compounds from the coupling reaction of diazobenzothiazole ions and acetaminophen
title_full_unstemmed	Synthesis, characteristic fragmentation patterns, and antibacterial activity of new azo compounds from the coupling reaction of diazobenzothiazole ions and acetaminophen
title_sort	synthesis, characteristic fragmentation patterns, and antibacterial activity of new azo compounds from the coupling reaction of diazobenzothiazole ions and acetaminophen
publisher	De Gruyter
publishDate	2021
url	https://doaj.org/article/a424b438e3fb4995b7554e74f2442895
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Synthesis, characteristic fragmentation patterns, and antibacterial activity of new azo compounds from the coupling reaction of diazobenzothiazole ions and acetaminophen

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