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1995 Fiscal Year Final Research Report Summary

Development of Antifungal Hypervalent Iodonium Salts

Research Project

Project/Area Number 05557098
Research Category

Grant-in-Aid for Developmental Scientific Research (B)

Allocation TypeSingle-year Grants
Research Field Chemical pharmacy
Research InstitutionTokushima University

Principal Investigator

OCHIAI Masahito  Tokushima University, Pharmaceutical Sciences, Professor, 薬学部, 教授 (50127065)

Co-Investigator(Kenkyū-buntansha) NAKAIKE Shiro  Taishou Pharmaceutical Co.Ltd., Research Center, Senior Scientist, 薬理研究部, 主任研究員
Project Period (FY) 1993 – 1995
Keywordsiodonium salt / antifungal activity / iodine / hypervalent
Research Abstract

A variety of alkenyl- and alkynyl (phenyl) iodonium tetrafluoroborates were prepared from organosilanes. The in vitro and in vivo antifungal activity of the iodonium salts were studied and compared with that of amphotericin B,5-fluorocytosine, clotrimazole, and ketoconazole. The following results were obtained :
1) (E)-1-Decenyl (phenyl) iodonium, 3-cyclopentyl-2-methylpropenyl (phenyl)-iodonium, and 2-methyl-3-phenylpropenyl (phenyl) iodonium tetrafluoroborates showedthe weak in vitro antifungal activity.
2) n-Octynyl-, n-nonynyl, and n-undecynyl (phenyl) iodonium tetrafluoroborates were found to have a broad in vitro antifungal activity at low drug concentrations, inhibiting growth of Candida albicans, Candida albicans, Candida kursei, Candida tropicalis, Cryptococcous neoformans, Cryptococcous neoformans, Aspergillus fumigatus, Microsporum canis, Trichophyton mentagrophytes, Trichophyton rubrum. The activity varied remarkably with the culture medium : in the yeast nitrogen base agar at ph 5.6 the antifungal activity was observed.
3) These alkenyl- and alkynyl (phenyl) iodonium tetrafluoroborates showed no in vivo antifungal activity.

  • Research Products

    (10 results)

All Other

All Publications (10 results)

  • [Publications] Takema Nagaoka: "An Onium Transfer Reaction of 1-Alkynyl (phenyl) iodonium Tetrafluoroborates with Triphenylarsine ; Synthesis of 1-Alkynyl (triphenyl) arsonium Tetrafluoroborates" Tetrahedron Letters. 36. 261-264 (1995)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Masahito Ochiai: "Solvent Effects on Ipso versus Ortho Selectivity in the Reductive Iodonio-Claisen Rearrangement of Allenyl (p-methoxyphenyl) iodane" J.Org.Chem.60. 2274-2275 (1995)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Tadshi Okuyama: "Solvolysis of Cyclohexenyliodonium Salt,a New Precursor for the Vinyl Cation : Remarkable Nucleofugality of the Phenyl-iodonio Group and Evidence for Internal Return from an Intimate Ion-Molecute Pair" J.Am.Chem.Soc.117. 3360-3367 (1995)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Masahito Ochiai: "Nature of Alkylidenecarbenes Generated from Alkenyl (phenyl) iodonium Tetrafluoroborates via Base-Induced α-Elimina-tion" J.Org.Chem.60. 2624-2626 (1995)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Yukio Masaki: "Alcoholysis of Epoxides Catalyzed by Tetracyanoethylene and Dicyanoketene Acetals" Bull.Chem.Soc.Jpn.69. 195-205 (1996)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] T.Nagaoka, T.Sueda, and M.Ochiai: "An Onium Transfer Reaction of 1-Alkynyl (phenyl)-iodonium Tetrafluoroborates with Triphenylarsine ; Synthesis of 1-Alkynyl (triphenyl) arsonium Tetrafluoroborates" Tetrahedron Lett.36. 261-264 (1995)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] M.Ochiai and T.Ito: "Solvent Effects on Ipso versus Ortho Selectivity in the Reductive Iodonio-Claisen Rearrangement of Allenyl (p-methoxyphenyl) iodane" J.Org.Chem.60. 2274-2275 (1995)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] T.Okuyama, T.Takino, T.Sueda, and M.Ochiai: "Solvolysis of Cyclohexenyliodonium Salt, a New Precursor for the Vinyl Cation : Remarkable Nucleofugality of the Phenyl-iodonio Group and Evidence for Internal Return from an Intimate Ion-Molecule Pair" j.Am.Chem.Soc.117. 3360-3367 (1995)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] M.Ochiai, T.Sueda, K.Uemura, and Y.Masaki: "Nature of Alkylidenecarbenes Generated from Alkenyl (phenyl) iodonium Tetrafluoroborates via Base-Induced alpha-Elimination" j.Org.Chem. 60. 2624-2626 (1995)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Y.Masaki, T.Mira, and M.Ochiai: "Alcoholysis of Epoxides Catalyzed by Tetracyanoethylene and Dicyanoketene Acetals" Bull.Chem.Soc.Jpn.69. 195-205 (1996)

    • Description
      「研究成果報告書概要(欧文)」より

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Published: 1997-03-04  

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