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Synthesis, Properties and Antimicrobial Activity of 5-Trifluoromethyl-2-formylphenylboronic Acid

2-Formylphenylboronic acids display many interesting features, not only from synthetic but also from an application as well as structural points of view. 5-Trifluoromethyl-2-formyl phenylboronic acid has been synthesized and characterized in terms of its structure and properties. The presence of an...

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Autores principales: Adamczyk-Woźniak, Agnieszka, Gozdalik, Jan T., Wieczorek, Dorota, Madura, Izabela D., Kaczorowska, Ewa, Brzezińska, Ewa, Sporzyński, Andrzej, Lipok, Jacek
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2020
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7070739/
https://www.ncbi.nlm.nih.gov/pubmed/32059517
http://dx.doi.org/10.3390/molecules25040799
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author Adamczyk-Woźniak, Agnieszka
Gozdalik, Jan T.
Wieczorek, Dorota
Madura, Izabela D.
Kaczorowska, Ewa
Brzezińska, Ewa
Sporzyński, Andrzej
Lipok, Jacek
author_facet Adamczyk-Woźniak, Agnieszka
Gozdalik, Jan T.
Wieczorek, Dorota
Madura, Izabela D.
Kaczorowska, Ewa
Brzezińska, Ewa
Sporzyński, Andrzej
Lipok, Jacek
author_sort Adamczyk-Woźniak, Agnieszka
collection PubMed
description 2-Formylphenylboronic acids display many interesting features, not only from synthetic but also from an application as well as structural points of view. 5-Trifluoromethyl-2-formyl phenylboronic acid has been synthesized and characterized in terms of its structure and properties. The presence of an electron-withdrawing substituent results in a considerable rise in the acidity in comparison with its analogues. In some solutions, the title compound isomerizes with formation of the corresponding 3-hydroxybenzoxaborole. Taking into account the probable mechanism of antifungal action of benzoxaboroles, which blocks the cytoplasmic leucyl-tRNA synthetase (LeuRS) of the microorganism, docking studies with the active site of the enzymes have been carried out. It showed possible binding of the cyclic isomer into the binding pocket of Candida albicans LeuRS, similar to that of the recently approved benzoxaborole antifungal drug (AN2690, Tavaborole, Kerydin). In case of Escherichia coli LeuRS, the opened isomer displays a much higher inhibition constant in comparison with the cyclic one. The antimicrobial activity of the title compound was also investigated in vitro, showing moderate action against Candida albicans. The compound reveals higher activity against Aspergillus niger as well as bacteria such as Escherichia coli and Bacillus cereus. In case of Bacillus cereus, the determined Minimum Inhibitory Concentration (MIC) value is lower than that of AN2690 (Tavaborole). The results confirm potential of 2-formylphenylboronic acids as antibacterial agents and give a hint of their possible mechanism of action.
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spelling pubmed-70707392020-03-19 Synthesis, Properties and Antimicrobial Activity of 5-Trifluoromethyl-2-formylphenylboronic Acid Adamczyk-Woźniak, Agnieszka Gozdalik, Jan T. Wieczorek, Dorota Madura, Izabela D. Kaczorowska, Ewa Brzezińska, Ewa Sporzyński, Andrzej Lipok, Jacek Molecules Article 2-Formylphenylboronic acids display many interesting features, not only from synthetic but also from an application as well as structural points of view. 5-Trifluoromethyl-2-formyl phenylboronic acid has been synthesized and characterized in terms of its structure and properties. The presence of an electron-withdrawing substituent results in a considerable rise in the acidity in comparison with its analogues. In some solutions, the title compound isomerizes with formation of the corresponding 3-hydroxybenzoxaborole. Taking into account the probable mechanism of antifungal action of benzoxaboroles, which blocks the cytoplasmic leucyl-tRNA synthetase (LeuRS) of the microorganism, docking studies with the active site of the enzymes have been carried out. It showed possible binding of the cyclic isomer into the binding pocket of Candida albicans LeuRS, similar to that of the recently approved benzoxaborole antifungal drug (AN2690, Tavaborole, Kerydin). In case of Escherichia coli LeuRS, the opened isomer displays a much higher inhibition constant in comparison with the cyclic one. The antimicrobial activity of the title compound was also investigated in vitro, showing moderate action against Candida albicans. The compound reveals higher activity against Aspergillus niger as well as bacteria such as Escherichia coli and Bacillus cereus. In case of Bacillus cereus, the determined Minimum Inhibitory Concentration (MIC) value is lower than that of AN2690 (Tavaborole). The results confirm potential of 2-formylphenylboronic acids as antibacterial agents and give a hint of their possible mechanism of action. MDPI 2020-02-12 /pmc/articles/PMC7070739/ /pubmed/32059517 http://dx.doi.org/10.3390/molecules25040799 Text en © 2020 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (http://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Adamczyk-Woźniak, Agnieszka
Gozdalik, Jan T.
Wieczorek, Dorota
Madura, Izabela D.
Kaczorowska, Ewa
Brzezińska, Ewa
Sporzyński, Andrzej
Lipok, Jacek
Synthesis, Properties and Antimicrobial Activity of 5-Trifluoromethyl-2-formylphenylboronic Acid
title Synthesis, Properties and Antimicrobial Activity of 5-Trifluoromethyl-2-formylphenylboronic Acid
title_full Synthesis, Properties and Antimicrobial Activity of 5-Trifluoromethyl-2-formylphenylboronic Acid
title_fullStr Synthesis, Properties and Antimicrobial Activity of 5-Trifluoromethyl-2-formylphenylboronic Acid
title_full_unstemmed Synthesis, Properties and Antimicrobial Activity of 5-Trifluoromethyl-2-formylphenylboronic Acid
title_short Synthesis, Properties and Antimicrobial Activity of 5-Trifluoromethyl-2-formylphenylboronic Acid
title_sort synthesis, properties and antimicrobial activity of 5-trifluoromethyl-2-formylphenylboronic acid
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7070739/
https://www.ncbi.nlm.nih.gov/pubmed/32059517
http://dx.doi.org/10.3390/molecules25040799
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