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Open AccessArticle

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

1
Faculty of Chemistry, Warsaw University of Technology, ul. Noakowskiego 3, 00-664 Warsaw, Poland
2
Faculty of Chemistry, University of Opole, ul. Oleska 48, 45-042 Opole, Poland
*
Author to whom correspondence should be addressed.
Molecules 2020, 25(4), 799; https://doi.org/10.3390/molecules25040799 (registering DOI)
Received: 3 December 2019 / Revised: 5 February 2020 / Accepted: 6 February 2020 / Published: 12 February 2020
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. View Full-Text
Keywords: acidity; antimicrobial; benzoxaborole; crystal; docking; equilibrium; formyl; Kerydin; phenylboronic; Tavaborole; trifluoromethyl acidity; antimicrobial; benzoxaborole; crystal; docking; equilibrium; formyl; Kerydin; phenylboronic; Tavaborole; trifluoromethyl
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MDPI and ACS Style

Adamczyk-Woźniak, A.; Gozdalik, J.T.; Wieczorek, D.; Madura, I.D.; Kaczorowska, E.; Brzezińska, E.; Sporzyński, A.; Lipok, J. Synthesis, Properties and Antimicrobial Activity of 5-Trifluoromethyl-2-formylphenylboronic Acid. Molecules 2020, 25, 799.

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