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Molecules 2014, 19(8), 11077-11095; doi:10.3390/molecules190811077
Article

Activity of Antifungal Organobismuth(III) Compounds Derived from Alkyl Aryl Ketones against S. cerevisiae: Comparison with a Heterocyclic Bismuth Scaffold Consisting of a Diphenyl Sulfone

1,* , 1, 2 and 2
1 Graduate School of Medicine, Yamaguchi University, Yamaguchi 753-8512, Japan 2 Graduate School of Science and Engineering, Yamaguchi University, Yamaguchi 753-8512, Japan
* Author to whom correspondence should be addressed.
Received: 27 May 2014 / Revised: 19 July 2014 / Accepted: 21 July 2014 / Published: 29 July 2014
(This article belongs to the Special Issue Heterocyclic and Medicinal Chemistry)
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Abstract

A series of hypervalent organobismuth(III) compounds derived from alkyl aryl ketones [XBi(5-R'C6H3-2-COR)(Ar)] was synthesized to investigate the effect of the compounds’ structural features on their antifungal activity against the yeast Saccharomyces cerevisiae. In contrast to bismuth heterocycles [XBi(5-RC6H3-2-SO2C6H4-1'-)] derived from diphenyl sulfones, a systematic quantitative structure-activity relationship study was possible. The activity depended on the Ar group and increased for heavier X atoms, whereas lengthening the alkyl chain (R) or introducing a substituent (R') reduced the activity. IBi(C6H4-2-COCH3)(4-FC6H4) was the most active. Its activity was superior to that of the related acyclic analogues ClBi[C6H4-2-CH2N(CH3)2](Ar) and ClBi(C6H4-2-SO2 tert-Bu)(Ar) and also comparable to that of heterocyclic ClBi(C6H4-2-SO2C6H4-1'-), which was the most active compound in our previous studies. Density function theory calculations suggested that hypervalent bismuthanes undergo nucleophilic addition with a biomolecule at the bismuth atom to give an intermediate ate complex. For higher antifungal activity, adjusting the lipophilicity-hydrophilicity balance, modeling the three-dimensional molecular structure around the bismuth atom, and stabilizing the ate complex appear to be more important than tuning the Lewis acidity at the bismuth atom.
Keywords: bismuth; Lewis acidity; hypervalent; S. cerevisiae; antifungal activity; acetophenone bismuth; Lewis acidity; hypervalent; S. cerevisiae; antifungal activity; acetophenone
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).
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Murafuji, T.; Tomura, M.; Ishiguro, K.; Miyakawa, I. Activity of Antifungal Organobismuth(III) Compounds Derived from Alkyl Aryl Ketones against S. cerevisiae: Comparison with a Heterocyclic Bismuth Scaffold Consisting of a Diphenyl Sulfone. Molecules 2014, 19, 11077-11095.

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