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Precise Synthesis of C-Nucleosides and Relation ship between their Structures and Biological Activity

Research Project

Project/Area Number 07554085
Research Category

Grant-in-Aid for Scientific Research (A)

Allocation TypeSingle-year Grants
Section展開研究
Research Field Organic chemistry
Research InstitutionChiba University

Principal Investigator

YOYOYAMA Masataka  Faculty of Science, Chiba Uni.Prof., 理学部, 教授 (00009052)

Co-Investigator(Kenkyū-buntansha) KUDO Masaaki  Japan Agro Co.Reseacher, 研究員
OKURI Naotake  Japan Analytical Co.Director, 研究所員
Project Period (FY) 1995 – 1997
Project Status Completed (Fiscal Year 1997)
Budget Amount *help
¥2,600,000 (Direct Cost: ¥2,600,000)
Fiscal Year 1997: ¥1,200,000 (Direct Cost: ¥1,200,000)
Fiscal Year 1996: ¥1,400,000 (Direct Cost: ¥1,400,000)
KeywordsC-Azanucleosides / C-Azadeoxynucleosides / Furanosylribose / Furanosyldeoxyribose / Anti-HIV-I / C-Azalyxonucleosides / 抗エイズ剤 / β-選択的合成 / C-ヌクレオシド / 抗HIV / C-ヘテロ原子-ヌクレオシド / 立体選択的合成 / 生物活性評価 / C-リボヌクレオシド / C-デオキシリボヌクレオシド
Research Abstract

In the viewpoint of biological activity, especially such as antiviral drugs, the C-nucleoside like showdomycin and the azasugar like nojirimycin have been known as naturally occurring and potential compounds. As a part of our program for synthesis and evaluation of a new type of DNA subunits, we intended to synthesize the nucleosides such as C-azanucleosides and C-azadeoxy-nucleosides, which have the structual skeletons similar to two compounds mentioned above : That is, the nucleosides which have a C-C bond between sugar's anomeric position and base moiety, and further, the endocyclic ribosyl or deoxyribosyl ring oxygen is replaced with nitrogen atom. To our best knowledge, the syntheses of three known C-azanucleosides have required unavailable starting materials or contained many difficult synthetic steps. Therefore, we developed a general method for the synthesis of gram quantities of C-azanucleosides, which was C-azalyxonucleosides by X-ray analysis. As the extention of this investigation, we reported the first synthesis of both C-azadeoxylyxonucleosides and C-azalyxonucleosides bearing a natural type of base such as uracil, azapseudouridine and further, their properties and biological activities.

Report

(4 results)
  • 1997 Annual Research Report   Final Research Report Summary
  • 1996 Annual Research Report
  • 1995 Annual Research Report
  • Research Products

    (34 results)

All Other

All Publications (34 results)

  • [Publications] 横山 正孝: "Cyclic Amination onto Aromatic Ring via Radical Pathway with (Diacetoxyiodo)arenes" Phosphorus,Suefur,and Silicon. 120. 449-450 (1997)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] 横山 正孝: "Novel Water-soluble Organosilane Compounds as a Radical Reducing Agent in Aqueous Media" Bull.Chem.Soc.Jpn.70. 2519-2523 (1997)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] 横山 正孝: "Strategic Approach to C-Nucleosides via Sugar Anomeric Radical,Cation,and Anion withSugarTellurides" Tetrahedron Lett.38. 5541-5544 (1997)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] 横山 正孝: "Studies on the Formation of Alkyl Radioals from Alkyl Aryl Tellurides and Their Application to the Synthesis" Heteroatom Chemistry. 8. 411-419 (1997)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] 横山 正孝: "Formation and Synthetic USE of Oxygen-centered Radioals with (Diacetoxyiodo)arenes" J.Chem.Soc.,Perkin Trains.1. 787-793 (1997)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] 横山 正孝: "Stereoselective Coupling of Riboses with Metallic salts of Aromatic Heterocycles" J.Che.Soc.,Perkin Trans.1. 29-33 (1997)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] H.Togo, Y.Hoshina, M.Yokoyama: "Cyclic Amination onto Aromatic Ring via Radical Pathway with (Diacetoxyiodo) arenes" Phosphorus, Sulfur, and Silicon. 120. 449-450 (1997)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] O.Yamazaki, H.Togo, G.Nogami, M.Yokoyama: "Novel Water-soluble Organosilane Compounds as a Radical Reducing Agent in Aqueous Media" Bull.Chem.Soc.Jpn.70. 2519-2523 (1997)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] W.Hei, H.Togo, M.Yokoyama: "Strategic Approach to C-Nucleosides via Sugar Anomeric Radical, Cation, and Anion with Sugar Tellurides" Tetrahedron Lett.38. 5541-5544 (1997)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] W.He, H.Togo, H.Ogawa, M.Yokoyama: "Studies on the Formation of Alkyl Radicals from Alkyl Aryl Tellurides and Their Application to the Synthesis of Carbocyclic C-Nucleosides Analogs" Heteroatom Chemistry. 8. 411-419 (1997)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] H.Togo, M.Katohgi, M.Yokoyama: "Direct Preparation of Saccharin Skeleton from N-Methyl o-Methylarenesufonamides wit (Diacetoxyiodo) arenes" Synlett. (in press.).

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] T.Muraki, H.Togo, M.Yokoyama: "Synthetic Use of 1- (p-Toluenesufonyloxy) -1,2-benziodoxol-3 (1H) -one : Iodination of Aromatic Rings" Synlett. (in press.).

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] T.Muraki, H.Togo, M.Yokoyama: "Hypervalent Iodine Compounds as Free Radical Precursors" Review on Heteroatom Chemistry. 17. 213-243 (1997)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] M.Yokoyama, H.Toyoshima, M.Shimizu, J.Mito, and H.Togo: "Simple Synthetic Method for Aromatic beta-C-Nucleosides via Coupling of Aryl Grignard Reagents with Sugar Fluorides" Synthesis. (in press). (1997)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] H.Togo, K.Muraki, Y.Hoshina, K.Yamaguchi, and M.Yokoyama: "Formation and Synthetic Use of Oxygen-centered Radicals with (Diacetoxyiodo) arenes" J.Chem.Soc., Perkin Trans.1. 787-793 (1997)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] M.Yokoyama, H.Toyoshima, M.Shimizu, H.Togo: "Stereosilective Coupling of Riboses with Metallic Salts of Aromatic Heterocycles" J.Chem.Soc., Perkin 1. 29-33 (1967)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] H.Togo, Y.Hoshina, G.Nogami, M.Yokoyama: "Radical Reactions with Trivalent Iodine Compounds" J.Synth.Org.Chem. (Japanese). 55. 90-98 (1997)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] 横山正孝: "Cyclic Amination on to Aromatic Ring via Radical Pathway with (Diacetoxyiodo)arenes" Phosphorus, Suefur, and Silicon. 120. 449-450 (1997)

    • Related Report
      1997 Annual Research Report
  • [Publications] 横山正孝: "Novel Water-soluble Organosilane Compounds as a Radical Reduiing Agent in Aqueous Media" Bull. Chem. Soc. Jpn.70. 2519-2523 (1997)

    • Related Report
      1997 Annual Research Report
  • [Publications] 横山正孝: "Strategic Approach to C-Nucleosides via Sugar Anomeric Radical, Cation, and Anion with Sugar Tellurides" Tetiahedron Lett.38. 5541-5544 (1997)

    • Related Report
      1997 Annual Research Report
  • [Publications] 横山正孝: "Studies on the Formation of Alkyl Radioals from Alkyl Aryl Tellurides and Their Application to the Synthesis" Heteroatom Chemistry. 8. 411-419 (1997)

    • Related Report
      1997 Annual Research Report
  • [Publications] 横山正孝: "Formation and Synthetic Use of Oxygen-centered Radioals with(Diacetoxyiodo)arenes" J. Chem. Soc., Perkin Trains. 1. 787-793 (1997)

    • Related Report
      1997 Annual Research Report
  • [Publications] 横山正孝: "Stereo selective Coupling of Riboses with Metallic salts of Aromatic Heterocycles" J. Chem. Soc., Perkin Trans. 1. 29-33 (1997)

    • Related Report
      1997 Annual Research Report
  • [Publications] 横山正孝: "Synthesis of C-Nucleosides uia Coupling of Ribosyl Flusride with Typical Aromatic Heterocyles" Heteroatom Chemistry. 6. 189-193 (1995)

    • Related Report
      1996 Annual Research Report
  • [Publications] 横山正孝: "Synthesis of C-Deoxyribonucleosides Bearing Typical Aromatic Heterocyles as Base Moiety" Synthesis. 638-640 (1995)

    • Related Report
      1996 Annual Research Report
  • [Publications] 横山正孝: "A Convenient Method for C-Azanucleosides Synthesis" Journal of Organic Chemistry. 61. 6079-6082 (1996)

    • Related Report
      1996 Annual Research Report
  • [Publications] 横山正孝: "Coupling of Ribofuranosyl Fluoride and Indoles" Journal of the Chemical Society,Perkin 1. 2145-2149 (1996)

    • Related Report
      1996 Annual Research Report
  • [Publications] 横山正孝: "Stereoselective Coupling of Riboses with Metallic Salts of Aromatic Heterocycles" Journal of the Chemical Society,Perkin 1. 29-33 (1997)

    • Related Report
      1996 Annual Research Report
  • [Publications] M. Yokoyama et al.: "Synthesis of Pyrrole Derivatives Using Thioimidate" Bull. Chem. Soc. Jpn. 68. 2735-2738 (1995)

    • Related Report
      1995 Annual Research Report
  • [Publications] M. Yokoyama et al.: "Synthesis of C-Deoxyribonucleosides Bearing Tyspical Aromatic Heterocycles as Base Moiety" Synthesis. 638-640 (1995)

    • Related Report
      1995 Annual Research Report
  • [Publications] M. Yokoyama et al.: "Synthesis of Tetrazales Bearing A Sugar Moiety" J. Chem. Soc.,Perkin1. 1747-1753 (1995)

    • Related Report
      1995 Annual Research Report
  • [Publications] M. Yokoyama et al.: "Synthesis of C-Nucleosides via Coupling of Ribosyl Fluoride and Typical Aromatic Heterocycles Bearing TMS Group" Heteroatom Chemistry. 6. 189-193 (1995)

    • Related Report
      1995 Annual Research Report
  • [Publications] S. Ishigami et al.: "Reaclivity of Carbocyclic Four-membered Radioals for the Preparation of Carbocyclic Analogues of Oxetanocins" J. Chem. Soc., Perkin 1. 2407-2412 (1994)

    • Related Report
      1995 Annual Research Report
  • [Publications] M. Yokoyama et al.: "Synthesis of C-Ribonucleosides Having Typical Aromatic Heterocycles as Base Moiety" Chem. Lett.265-268 (1994)

    • Related Report
      1995 Annual Research Report

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Published: 1996-04-01   Modified: 2016-04-21  

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