The influence of fluorine position on the properties of fluorobenzoxaboroles

The influence of fluorine position on the properties of fluorobenzoxaboroles

[Display omitted] •Four isomers of fluoro-substituted benzoxaboroles: synthesis, multinuclear NMR, pKa.•Activity against several fungi.•6-Fluorobenzoxaborole: molecular and crystal structure compared with AN2690. 5-Fluoro-2,1-benzoxaborol-1(3H)-ol, a potent antifungal drug also known as Tavaborole o...

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Veröffentlicht in:Bioorganic chemistry 2015-06, Vol.60, p.130-135
Hauptverfasser: Adamczyk-Woźniak, Agnieszka, Cabaj, Małgorzata K., Dominiak, Paulina M., Gajowiec, Patrycja, Gierczyk, Błażej, Lipok, Jacek, Popenda, Łukasz, Schroeder, Grzegorz, Tomecka, Ewelina, Urbański, Piotr, Wieczorek, Dorota, Sporzyński, Andrzej
Format: Artikel
Sprache:eng
Schlagworte:
Antifungal activity
Antifungal Agents - chemistry
Antifungal Agents - pharmacology
Benzoxaboroles
Boron Compounds - chemistry
Boron Compounds - pharmacology
Bridged Bicyclo Compounds, Heterocyclic - chemistry
Bridged Bicyclo Compounds, Heterocyclic - pharmacology
Crystal structure
Crystallography, X-Ray
Fluorine - chemistry
Fluorine - pharmacology
Fungi - drug effects
Halogenation
Humans
Isomerism
Magnetic Resonance Spectroscopy
Models, Molecular
Mycoses - drug therapy
Tavaborole
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Zusammenfassung:[Display omitted] •Four isomers of fluoro-substituted benzoxaboroles: synthesis, multinuclear NMR, pKa.•Activity against several fungi.•6-Fluorobenzoxaborole: molecular and crystal structure compared with AN2690. 5-Fluoro-2,1-benzoxaborol-1(3H)-ol, a potent antifungal drug also known as Tavaborole or AN2690, has been compared with its three isomers in terms of its activity against several fungi as well as pKa and multinuclear NMR characterization. The molecular and crystal structure of 6-fluoro-2,1-benzoxaborol-1(3H)-ol was determined and compared with that of AN2690.
ISSN:0045-2068
1090-2120
DOI:10.1016/j.bioorg.2015.05.004