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Paper | Regular issue | Vol 96, No. 6, 2018, pp.1037-1052
Published online, 16th May, 2018
DOI: 10.3987/COM-18-13876
Synthesis and Antifungal Activities of Pyridine Bioisosteres of a Bismuth Heterocycle Derived from Diphenyl Sulfone

A. F. M. Hafizur Rahman, Toshihiro Murafuji,* Kazuki Yamashita, Masahiro Narita, Isamu Miyakawa, Yuji Mikata, Katsuya Ishiguro, and Shin Kamijo

*Graduate School of Medicine, Yamaguchi University, 1677-1 Yoshida, Yamaguchi 753-8512, Japan

Abstract

Heterocyclic iodobismuthanes 79 [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 79 affects their activities. The antifungal activities of 79 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.