Faculty of Chemistry, Warsaw University of Technology, ul. Noakowskiego 3, 00-664 Warsaw, Poland.
Faculty of Chemistry, University of Opole, ul. Oleska 48, 45-042 Opole, Poland.
Molecules. 2020 Feb 12;25(4):799. doi: 10.3390/molecules25040799.
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 3hydroxybenzoxaborole. 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 LeuRS, similar to that of the recently approved benzoxaborole antifungal drug (, Tavaborole, Kerydin). In case of 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 , showing moderate action against . The compound reveals higher activity against as well as bacteria such as and . In case of , the determined Minimum Inhibitory Concentration (MIC) value is lower than that of (Tavaborole). The results confirm potential of 2-formylphenylboronic acids as antibacterial agents and give a hint of their possible mechanism of action.
2-甲酰基苯硼酸具有许多有趣的特性，不仅在合成方面，而且在应用和结构方面也是如此。5-三氟甲基-2-甲酰基苯硼酸已被合成并从其结构和性质方面进行了表征。与类似物相比，吸电子取代基的存在导致酸度显著升高。在某些溶液中，标题化合物会异构化形成相应的 3-羟基苯并恶硼烷。考虑到苯并恶硼烷可能的抗真菌作用机制，它可以阻断微生物细胞质亮氨酰-tRNA 合成酶（LeuRS），因此对酶的活性位点进行了对接研究。结果表明，环状异构体可能与最近批准的苯并恶硼烷抗真菌药物（Tavaborole，Kerydin）一样结合到 LeuRS 的结合口袋中。对于 LeuRS，开环异构体的抑制常数明显高于环状异构体。还研究了标题化合物的抗菌活性，显示出对的中等抑制作用。该化合物对 和 等细菌的活性更高，如 和 。对于 ，确定的最小抑菌浓度（MIC）值低于 （Tavaborole）。结果证实了 2-甲酰基苯硼酸作为抗菌剂的潜力，并提示了其可能的作用机制。
