甲酰基苯硼酸的抗真菌活性和互变异构平衡。

Antifungal activity and tautomeric cyclization equilibria of formylphenylboronic acids.

机构信息

Faculty of Chemistry, Warsaw University of Technology, Noakowskiego 3, 00-664 Warsaw, Poland.

Faculty of Chemistry, Opole University, Oleska 48, 45-052 Opole, Poland.

出版信息

Bioorg Chem. 2019 Oct;91:103081. doi: 10.1016/j.bioorg.2019.103081. Epub 2019 Jun 25.

DOI:10.1016/j.bioorg.2019.103081

PMID:31445482

Abstract

2-Formylphenylboronic acid and four isomeric fluoro-2-formylphenylboronic acids have been found active against a series of fungal strains: Aspergillus, Fusarium, Penicillium and Candida. The level of antifungal activity was evaluated by agar diffusion tests as well as the determination of minimum inhibitory concentrations (MICs) by serial dilution method. Among the tested compounds, 4-fluoro-2-formylphenylboronic acid - an analogue of the known antifungal drug Tavaborole (AN2690) - proved to be the most potent antifungal agent. The tautomeric equilibrium leading to the formation of 3-hydroxybenzoxaboroles as well as the position of the fluorine substituent were revealed to play a crucial role in the observed activity.

摘要

2-甲酰基苯硼酸和四种同分异构的氟-2-甲酰基苯硼酸已被发现对一系列真菌菌株具有活性：曲霉属、镰刀菌属、青霉属和念珠菌属。通过琼脂扩散试验评估抗真菌活性，以及通过连续稀释法测定最小抑菌浓度（MICs）。在所测试的化合物中，4-氟-2-甲酰基苯硼酸——一种已知抗真菌药物塔沃泊莱（AN2690）的类似物——被证明是最有效的抗真菌剂。导致形成 3-羟基苯并恶硼烷的互变异构平衡以及氟取代基的位置被揭示在观察到的活性中起着关键作用。