title: Heterocyclic bismuth carboxylates based on a diphenyl sulfone scaffold: synthesis and antifungal activity against Saccharomyces cerevisiae.
abstract: A series of heterocyclic organobismuth(III) carboxylates 4 and 5 [RCO2Bi(C6H4-2-SO2C6H4-1'-)] derived from diphenyl sulfone was synthesized to determine the influence of the carboxylate ligand structure on the lipophilicity and antifungal activity against the yeast Saccharomyces cerevisiae. In contrast to the clear structure-activity relationship between the size of the inhibition zone and the value of ClogP for specific substitution on diphenyl sulfone scaffold 1 [ClBi(5-RC6H3-2-SO2C6H4-1'-)], scaffolds 4 and 5 showed similar inhibition activities irrespective of the ClogP value. This suggests that these molecules function inside the yeast cell by separating into the cationic heterocyclic bismuth scaffold and the anionic carboxylate moiety, and that the bismuth scaffold plays an important role in the inhibition activity.
authors.affiliation: Graduate School of Medicine, Yamaguchi University, Yamaguchi City 753-8512, Japan. murafuji@yamaguchi-u.ac.jp
authors.forename: Toshihiro
authors.initials: T
authors.lastname: Murafuji
authors.forename: Kunito
authors.initials: K
authors.lastname: Kitagawa
authors.forename: Daisuke
authors.initials: D
authors.lastname: Yoshimatsu
authors.forename: Kei
authors.initials: K
authors.lastname: Kondo
authors.forename: Katsuya
authors.initials: K
authors.lastname: Ishiguro
authors.forename: Ryo
authors.initials: R
authors.lastname: Tsunashima
authors.forename: Isamu
authors.initials: I
authors.lastname: Miyakawa
authors.forename: Yuji
authors.initials: Y
authors.lastname: Mikata
mesh_terms: D000935:Antifungal Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D001713:Biphenyl Compounds / Q000737:chemistry; D001729:Bismuth / Q000737:chemistry*; D002264:Carboxylic Acids / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D006571:Heterocyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D008055:Lipids / Q000737:chemistry; D008826:Microbial Sensitivity Tests; D008956:Models, Chemical; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D012441:Saccharomyces cerevisiae / Q000187:drug effects; D013329:Structure-Activity Relationship; D013450:Sulfones / Q000737:chemistry*
chemical_list: D000935:Antifungal Agents; D001713:Biphenyl Compounds; D001729:Bismuth; D002264:Carboxylic Acids; D006571:Heterocyclic Compounds; D008055:Lipids; D009942:Organometallic Compounds; D013450:Sulfones; C010574:biphenyl