Heterocycles p. 1037 - 1052 (2018)
Update date:2022-08-29
Topics:
Hafizur Rahman
Murafuji, Toshihiro
Yamashita, Kazuki
Narita, Masahiro
Miyakawa, Isamu
Mikata, Yuji
Ishiguro, Katsuya
Kamijo, Shin
– Heterocyclic iodobismuthanes 7–9 [IBi(C6H4-2-SO2C5H3N-1′-)] derived from phenyl pyridinyl sulfones were synthesized. Their antifungal activities against the yeast Saccharomyces cerevisiae were compared with those of halobismuthanes [XBi(RC6H3-2-SO2C6H4-1′-)] (1: X=Cl; 2: X=I, R=H) derived from diphenyl sulfone derivatives to determine how the bioisosteric replacement of the benzene ring in 2 with the pyridine ring in 7–9 affects their activities. The antifungal activities of 7–9 were higher or comparable to those of 1 and 2. The DFT calculations suggested that the generation of the antifungal activity of the bismuthanes was well understood by the nucleophilic addition of methanethiolate anion as a model biomolecule at the bismuth atom to give an intermediate ate complex.
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