Faculty of Chemistry, Warsaw University of Technology, Noakowskiego 3, Warsaw 00-664 , Poland.
Faculty of Chemistry, Warsaw University of Technology, Noakowskiego 3, Warsaw 00-664 , Poland.
Bioorg Chem. 2022 Feb;119:105560. doi: 10.1016/j.bioorg.2021.105560. Epub 2021 Dec 13.
The [2-formyl-4-(trifluoromethyl)phenyl]boronic acid as well as its benzoxaborole and bis(benzoxaborole) derivatives were obtained and their properties studied. The 2-formyl compound displays an unusual structure in the crystalline state, with a significant twist of the boronic group, whereas in DMSO solution it tautomerizes with formation of a cyclic isomer. All the studied compounds exhibit relatively high acidity as well as a reasonable antimicrobial activity. Docking studies showed interactions of all the investigated compounds with the binding pocket of Candida albicans LeuRS. High activity against Bacillus cereus was determined for the 2-formyl compound as well as for the novel bis(benzoxaborole), whereas the studied benzoxaborole shows high antifungal action with MIC values equal to 7.8and 3.9 μg/mL against C. albicans and A. niger respectively. None of the studied compounds exhibits reasonable activity against E. coli.
[2- 醛基-4-(三氟甲基)苯基]硼酸及其苯并恶硼唑和双(苯并恶硼唑)衍生物已被获得并研究了其性质。在结晶状态下，2- 醛基化合物表现出异常的结构，硼酸基团发生显著扭曲，而在 DMSO 溶液中，它通过形成环状互变异构体而互变异构。所有研究的化合物均表现出相对较高的酸度和合理的抗菌活性。对接研究表明，所有研究的化合物都与白色念珠菌 LeuRS 的结合口袋相互作用。新型双(苯并恶硼唑)以及 2- 醛基化合物对蜡状芽孢杆菌表现出高活性，而研究的苯并恶硼唑对白色念珠菌和黑曲霉的 MIC 值分别为 7.8 和 3.9μg/mL，表现出较高的抗真菌活性。研究的化合物均对大肠杆菌无合理的活性。
