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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
Received: 27 May 2014; in revised form: 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 which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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MDPI and ACS Style

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.

AMA Style

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(8):11077-11095.

Chicago/Turabian Style

Murafuji, Toshihiro; Tomura, Mai; Ishiguro, Katsuya; Miyakawa, Isamu. 2014. "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 19, no. 8: 11077-11095.


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