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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
Project Status Completed (Fiscal Year 1995)
Budget Amount *help
¥13,800,000 (Direct Cost: ¥13,800,000)
Fiscal Year 1995: ¥3,800,000 (Direct Cost: ¥3,800,000)
Fiscal Year 1994: ¥4,200,000 (Direct Cost: ¥4,200,000)
Fiscal Year 1993: ¥5,800,000 (Direct Cost: ¥5,800,000)
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.

Report

(4 results)
  • 1995 Annual Research Report   Final Research Report Summary
  • 1994 Annual Research Report
  • 1993 Annual Research Report
  • Research Products

    (24 results)

All Other

All Publications (24 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
    • Related Report
      1995 Final Research Report Summary
  • [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
    • Related Report
      1995 Final Research Report Summary
  • [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
    • Related Report
      1995 Final Research Report Summary
  • [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
    • Related Report
      1995 Final Research Report Summary
  • [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
    • Related Report
      1995 Final Research Report Summary
  • [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
    • Related Report
      1995 Final Research Report Summary
  • [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
    • Related Report
      1995 Final Research Report Summary
  • [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
    • Related Report
      1995 Final Research Report Summary
  • [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
    • Related Report
      1995 Final Research Report Summary
  • [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
    • Related Report
      1995 Final Research Report Summary
  • [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)

    • Related Report
      1995 Annual Research Report
  • [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)

    • Related Report
      1995 Annual Research Report
  • [Publications] Tadashi Okuyama: "Solvolysis of Cyclohexenyliodonium Salt,a New Precursor for the Vinyl Cation : Remarkable Nucleo-fugality of the Phenyl-iodonio Group" J.Am.Chem.Soc.117. 3360-3367 (1995)

    • Related Report
      1995 Annual Research Report
  • [Publications] Masahito Ochiai: "Nature of Alkylidenecarbenes Generated from Alkenyl (phenyl) iodonium Tetrafluoroborates via Base-Induced αElimina-tion" J.Org.Chem.60. 2624-2626 (1995)

    • Related Report
      1995 Annual Research Report
  • [Publications] Yukio Masaki: "Alcoholysis of Epoxides Catalyzed by Tetracyanoethylene and Dicyanoketene Acetals" Bull.Chem.Soc.Jpn.69. 195-205 (1996)

    • Related Report
      1995 Annual Research Report
  • [Publications] Masahito Ochiai: "Synthesis of (2)-1、2-Dihalo-1-alkenes by the Reaction of(2)-(B-Halovinyl)phenyliodonium salts with n-Bu4NX or KXICuX." Chemistry Lett.871-874 (1994)

    • Related Report
      1994 Annual Research Report
  • [Publications] Masahito Ochial: "Evidence for Michael-Type Reaction of Alkenyliodonium Salts." Tetrahedron Lett.35. 9407-9408 (1994)

    • Related Report
      1994 Annual Research Report
  • [Publications] Takema Nagaoka: "An Onium Transfer Reaction of 1-Alkynyl(phenyl)iodonium Tetraflueroborates with Triphenylarsine" Tetrahedron Lett.36. 261-264 (1995)

    • Related Report
      1994 Annual Research Report
  • [Publications] Masahito Ochial: "Solvent Effects on Ipso versus Ortho Selectivity." J.Org.Chem.(in press).

    • Related Report
      1994 Annual Research Report
  • [Publications] Masahito Ochial: "The Nature of Alkylidene carbenes." J.Org.Chem.(in press).

    • Related Report
      1994 Annual Research Report
  • [Publications] Tadashi Okuyama: "Solvolysis of Cyclohexenyliodonium Salt." J.Am.Chem.Soc.(in press).

    • Related Report
      1994 Annual Research Report
  • [Publications] Masahito Ochiai: "α-versus β-Elimination of (2)-(β-Halovinyl)iodonium Salts:Generation of (α-Haloalkylidene)carbenes" J.Am.Chem.Soc.115. 2528-2529 (1993)

    • Related Report
      1993 Annual Research Report
  • [Publications] Masahito Ochiai: "Synthesis of an (Alkylperoxy)-λ^3-iodane by the Reaction of 1-Hydroxy-1λ^3,2-benziodoxol-3(1H)-one with 1,3-Bis(trimethylsilyl)methylbutyne" J.Chem.Soc.,Chem.Commun.218-220 (1993)

    • Related Report
      1993 Annual Research Report
  • [Publications] Masahito Ochiai: "Nucleophilic Vinylic Substitutions of (2)-(β-(Phenylsultonyl)alkenyl)iodonium tetrafluoroborates with Sodium Benzenesulfinate" Tetrahedron Lett.34. 4829-4830 (1993)

    • Related Report
      1993 Annual Research Report

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Published: 1993-04-01   Modified: 2016-04-21  

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