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

Agnieszka Adamczyk-Woźniak , Jan Gozdalik , Dorota Wieczorek , Izabela Madura , Ewa Kaczorowska , Ewa Brzezińska , Andrzej Sporzyński , Jacek Lipok

Abstract

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.

Author Agnieszka Adamczyk-Woźniak (FC / DPC)
Agnieszka Adamczyk-Woźniak,,
- Department Of Physical Chemistry
, Jan Gozdalik (FC / DPC)
Jan Gozdalik,,
- Department Of Physical Chemistry
, Dorota Wieczorek
Dorota Wieczorek,,
-
, Izabela Madura (FC / CofIC)
Izabela Madura,,
- Chair Of Inorganic Chemistry
, Ewa Kaczorowska (FC / DPC)
Ewa Kaczorowska,,
- Department Of Physical Chemistry
, Ewa Brzezińska (WUT)
Ewa Brzezińska,,
- Warsaw University of Technology
, Andrzej Sporzyński (FC / DPC)
Andrzej Sporzyński,,
- Department Of Physical Chemistry
, Jacek Lipok
Jacek Lipok,,
-
Journal seriesMolecules, ISSN 1420-3049
Issue year2020
Vol25
ASJC Classification1605 Organic Chemistry
DOIDOI:10.3390/molecules25040799
Languageen angielski
Score (nominal)100
Score sourcejournalList
ScoreMinisterial score = 100.0, 05-08-2020, ArticleFromJournal
Publication indicators Scopus Citations = 1; Scopus SNIP (Source Normalised Impact per Paper): 2017 = 1.146; WoS Impact Factor: 2018 = 3.06 (2) - 2018=3.38 (5)
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