167771-87-1Relevant academic research and scientific papers
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
Murafuji, Toshihiro,Tomura, Mai,Ishiguro, Katsuya,Miyakawa, Isamu
, p. 11077 - 11095 (2014/10/15)
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-SO 2C6H4-1′-)] 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-COCH 3)(4-FC6H4) was the most active. Its activity was superior to that of the related acyclic analogues ClBi[C6H 4-2-CH2N(CH3)2](Ar) and ClBi(C 6H4-2-SO2 tert-Bu)(Ar) and also comparable to that of heterocyclic ClBi(C6H4-2-SO2C 6H4-1′-), 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.
Structure and spectroscopic characteristics of 2'-diethylboryl-4''- dimethylaminochalcone bearing an intramolecular boron-oxygen coordinate bond
Murafuji,Sugihara,Moriya,Mikata,Yano
, p. 683 - 685 (2008/10/08)
How formation of an intramolecular coordinate bond affects the molecular structure was examined in the structural comparison of 2'-diethylboryl-4''- dimethylaminochalcone (1) and 2'-ethylenedioxyboryl-4''-dimethylaminochalcone (2) with chloro-{2-[(4-dimethylaminostyryl) carbonyl] phenyl} (4-methyl- phenyl)] bismuthane (3) and 4''-dimethylaminochalcone (4).
Hypervalent bond formation in halogeno(2-acylphenyl)bismuthanes
Murafuji, Toshihiro,Mutoh, Takanori,Satoh, Kohichi,Tsunenari, Kazumi,Azuma, Nagao,Suzuki, Hitomi
, p. 3848 - 3854 (2008/10/09)
Hypervalent bond formation has been found to occur at bismuth as the hypervalent center. The transformation of (2-acetylphenyl)bis(4-methylphenyl)bismuthane (2b) to (2-acetylphenyl)bromo(4-methylphenyl)bismuthane (3b) brings about a noticeable change in the electronic nature of the carbonyl function in the 2-acetylphenyl group, which is sensitively reflected in the IR, 1H, and 13C NMR spectra of compound 3b. These spectral changes may be rationalized in terms of the formation of a hypervalent O-Bi-Br bond through intramolecular coordination of the carbonyl oxygen atom to the bismuth center. X-ray crystallography of 3b has confirmed this interpretation.
