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Synthesis of Monofluoro Building Blocks Designed from Fine Chemistry Viewpoint and Development of Fluorine-containing Medicinals

Research Project

Project/Area Number 02557086
Research Category

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

Allocation TypeSingle-year Grants
Research Field Chemical pharmacy
Research InstitutionToyama Medical & Pharmaceutical University

Principal Investigator

TAKEUCHI Yoshio  Toyama Medical & Pharmaceutical University Faculty of Pharmaceutical Sciences Associate Professor, 薬学部, 助教授 (20111750)

Co-Investigator(Kenkyū-buntansha) TAKAHASHI Tamiko  Toyama Medical & Pharmaceutical University Faculty of Pharmaceutical Sciences Re, 薬学部, 助手 (10115181)
ARAI Yoshitsugu  Toyama Medical & Pharmaceutical University Faculty of Pharmaceutical Sciences re, 薬学部, 助手 (10115157)
KOIZUMI Toru  Toyama Medical & Pharmaceutical Scieces Professor, 薬学部, 教授 (40012611)
Project Period (FY) 1990 – 1992
Project Status Completed (Fiscal Year 1992)
Budget Amount *help
¥5,400,000 (Direct Cost: ¥5,400,000)
Fiscal Year 1992: ¥800,000 (Direct Cost: ¥800,000)
Fiscal Year 1991: ¥1,000,000 (Direct Cost: ¥1,000,000)
Fiscal Year 1990: ¥3,600,000 (Direct Cost: ¥3,600,000)
KeywordsMonofluoro Building Blocks / Multifunctional Carbon Compounds / Tertiary Alkyl Fluorides / alpha-Fluoro-alpha-amino Acid / Fluorinated Tropanes / Fluorine-containing Medicinals / NMAD Receptor / Molecular Design / 合成ブロック / バートン法 / ブロモフルオロアルカン / モノフルオロ化合物 / フルオロエテン / トロパン / 光学活性 / 1,3双極付加
Research Abstract

1) Among the various monofluoro building blocks designed, 1-6, synthesis of the four compounds 1-4 was achieved. However, the isolation of the selenenyl derivative 5 and the fluoroethene equivalent 6 was unsuccessful due to the instability caused by the multifunctional carbon structures.
2) Synthesis of the chiral tropane precursors, 7 and 8, was achieved. However. further efforts to convert them into chiral tropanes was abandoned because this pathway involves some reactions with unsatisfactory yields.
3) As to the development of the general entry to the novel tertiary alkyl fluorides, we succeeded to get to the target structure 13 by two routes, i. e., the alkylation of 11 obtained from 9 via 10 and the alkylation of 12 obtained from 9.
4) The synthesis of various precursors for alpha-fluoro-alpha-amino acids, including 15 and 16, has been achieved. However, the target compounds could not be isolated due to the rather drastic reaction conditions employed for the final stage and also to the instability of the target compounds.
5) Four compounds 14-17 were tested for fencyclidine inhibitory activity and monofluorotropane 18 was tested for nicotinic activity. However, all of them were found to be not so effective as we had expected.

Report

(4 results)
  • 1992 Annual Research Report   Final Research Report Summary
  • 1991 Annual Research Report
  • 1990 Annual Research Report
  • Research Products

    (17 results)

All Other

All Publications (17 results)

  • [Publications] TAKEUCHI,Yoshio: "Synthetic Studies for Novel Structure of α-Nitrogenously Function-alized α-Fluorocarboxylic Acids.II.Synthesis and Some Reactions of α-Fluoro-α-nitrocarboxylic Ester and Carboxamide Derivatives" Chem.Pharm.Bull.39. 3120-3122 (1991)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1992 Final Research Report Summary
  • [Publications] TAKAHASHI,Tamiko: "Asymmetric 1,3-Dipolar Cycloaddition of Chiral Sulphinylethenes with 1-Methyl-3-Oxidopyridinium and Some Nitrones" Tetrahedron Asymmetry. 2. 1379-1390 (1991)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1992 Final Research Report Summary
  • [Publications] TAKEUCHI,Yoshio: "Chemistry of Novel Compounds with Multifunctional Carbon Structure.7.Synthetic Studies of the Potentially Versatile Monofluoro Mole-cules,α Functionalized α-Fluoro-βketoesters" J.Org.Chem.57. 2196-2199 (1992)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1992 Final Research Report Summary
  • [Publications] TAKEUCHI,Yoshio: "Development of Fluorine-Containing Building Building Blocks" Pharmacia. 27. 1036-1040 (1991)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1992 Final Research Report Summary
  • [Publications] TAKEUCHI,Yoshio: "The First General and Efficient Entry to the Synthesis of Tertiary Alkyl Fluorides" J.Org.Chem.

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1992 Final Research Report Summary
  • [Publications] TAKEUCHI,Yoshio: "Synthetic Studies for Novel Structure of α-Nitrogenously Function-alized α-Fluorocarboxylic Acids.II.Synthesis and Some Reactions of α-Azido-α-fluorocarboxylic Ester and Carboxamide Derivatives." Chem.Pharm.Bull.

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1992 Final Research Report Summary
  • [Publications] Y.Takeuchi, K Nagata, and T.Koizumi: "Synthetic Studies for Novel Structure of alpha-Nitrogenously Functionalized alpha-Fluorocarboxylic Acids. II. Synthesis and Some Reactions of alpha-Fluoro-alpha-nitrocarboxylic Ester and Carboxaminde Derivatives" Chem. Pharm. Bull.39. 3120-3122 (1991)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1992 Final Research Report Summary
  • [Publications] T.Takahashi, A.Fujii, J.Sugita, T.Hagi, K.Kitano, Y.Araki, T.Koizumi, and M.Shiro: "Asymmetric 1,3-Dipolar Cycloaddition of Chiral Sulphinylethenes with 1-Methyl-3-Oxidopyridinium and Some Nitrones" Tetrahedron: Asymmetry. 2. 1379-1390 (1991)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1992 Final Research Report Summary
  • [Publications] Y.Takeuchi: "Development of Fluorine-containing Building Blocks" Pharmacia. 27. 1036-1040 (1991)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1992 Final Research Report Summary
  • [Publications] Y.Takeuchi, H.Ogura, A.Kanada, and T.Koizumi: "Chemistry of Novel Compounds with Multifunctional Carbon Structure. 7. Synthetic Studies of the Potentially Versatile Monofluoro Molecules, alpha Functionalized alpha-Fluoro-beta-ketoesters" J. Org. Chem.57. 2196-2199 (1992)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1992 Final Research Report Summary
  • [Publications] Y.Takeuchi, A.Kanada, S.Kawahara, and T.Koizumi: "The First General and Efficient Entry to the Synthesis of Tertiary Alkyl Fluorides" J. Org. Chem.

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1992 Final Research Report Summary
  • [Publications] Y.Takeuhi, M.Nabetani, K.Takagi, and T.Koizumi: "Synthetic Studies for Novel Structure of alpha-Nitrogenously Functionalized alpha-Fluorocarboxylic. Acids. III. Synthesis and Some Reactions of alpha-Azido-alpha-fluorocarboxylic Ester and Carboxaminde Derivatives."

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1992 Final Research Report Summary
  • [Publications] Takeuchi,Yoshio: "Chemistry of Novel Compounds with Multifunctional Carbon Structure.7.Synthetic Studies of the Potentially Versatile Monofluoro Mole-cules, α Functionalized α-Fluoro-β-ketoesters" J.Org.Chem.57. 2196-2199 (1992)

    • Related Report
      1992 Annual Research Report
  • [Publications] Takeuchi,Yoshio: "Synthetic Studies for Novel Structure of α-Nitrogenously Functionalized α-Fluorocarboxylic Acids.II.Synthesis and Some Reactions of α-Fluoro-α-nitrocarboxylic Ester and Carboxamide Derivatives" Chem.Pharm.Bull.39. 3120-3122 (1991)

    • Related Report
      1991 Annual Research Report
  • [Publications] Takahashi,Tamiko: "Asymmetric 1,3-Dipolar Cycloaddition of Chiral Sulphinylethenes with 1-Methyl-3-Oxidopyridinium and Some Nitrones" Tetrahedron:Asymmetry. 2. 1379-1390 (1991)

    • Related Report
      1991 Annual Research Report
  • [Publications] Takeuchi,Yoshio: "Chemistry of Novel Compounds with Multifunctional Carbon Structure.7.Synthetic Studies of the Potentially Versatile Monofluoro Molecules,α Functionalized α-Fluoro-β-ketoesters" J.Org.Chem.

    • Related Report
      1991 Annual Research Report
  • [Publications] Takeuchi,Yoshio: "The First General and Efficient Entry to the Synthesis of Tertiary Alkyl Fluorides" J.Org.Chem.

    • Related Report
      1991 Annual Research Report

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Published: 1990-04-01   Modified: 2016-04-21  

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