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Drug creation involving hybrid type of low molecular weight biomolecules as lead compounds

Research Project

Project/Area Number 12672079
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeSingle-year Grants
Section一般
Research Field Chemical pharmacy
Research InstitutionKobe Pharmaceutical University

Principal Investigator

NAITO Takeaki  Kobe Pharmaceutical University, Professor, 薬学部, 教授 (00068339)

Co-Investigator(Kenkyū-buntansha) UEDA Masafumi  Kobe Pharmaceutical University, Assistant, 薬学部, 助手 (00340935)
MIYATA Okiko  Kobe Pharmaceutical University, Associate Professor, 薬学部, 助教授 (90102110)
宮部 豪人  神戸薬科大学, 薬学部, 助手 (10289035)
Project Period (FY) 2000 – 2002
Project Status Completed (Fiscal Year 2002)
Budget Amount *help
¥3,300,000 (Direct Cost: ¥3,300,000)
Fiscal Year 2002: ¥600,000 (Direct Cost: ¥600,000)
Fiscal Year 2001: ¥900,000 (Direct Cost: ¥900,000)
Fiscal Year 2000: ¥1,800,000 (Direct Cost: ¥1,800,000)
Keywordssugar / amino acid / radical / oxime ether / Dysiherbaine / Wittig rearrangement / 核酸塩基 / ワンポット / デシヘルベイン
Research Abstract

Research for exploring new lead compounds for new drugs has focused to one component of biological compounds and not to hybrid components so far. We started our project to develop the most efficient and practical synthetic method for biological hybrid compounds which consist of amino acids, sugars, and nucleic bases.
New synthetic method for amino acids and the related peptides has been developed via the route involving radical addition-cyclization of oxime ethers connected with olefins. The products were converted smoothly into β-amino acids.
We also investigated construction of sugar parts by the radical reactions of the unprotected natural sugars. Stannyl radical addition-cyclization of oxime ethers connected with the carbonyl group proceeded smoothly to afford cyclic amino alcohols which were converted into aminocyclitols. The radical reaction was found to proceed via the most stable transition state involving minimum 1, 3-allylic strain.
Formal synthesis of Dysiherbine was completed via two key reactions which are 1, 2-Wittig rearrangement and asymmetric hydroxylation respectively.

Report

(4 results)
  • 2002 Annual Research Report   Final Research Report Summary
  • 2001 Annual Research Report
  • 2000 Annual Research Report
  • Research Products

    (17 results)

All Other

All Publications (17 results)

  • [Publications] 宮部豪人: "Synthesis of Aminocyclohexitol by Carbon-Carbon Bond-Forming Radical Cyclization of Oxime Ether"Chem. Pharm. Bull.. 51. 100-103 (2003)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] 宮田興子: "Radical cyclization in heterocycle synthesis. Part 13.:Sulfanyl radical radical addtion-cyclization of oxime ethers and hydazone"Tetrahedron. 58. 4459-4479 (2002)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] 宮田興子: "A convenient route to the furopyran core of dysiherbaine"Org. Biomol. Chem.. 1. 772-774 (2003)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] Hideto Miyabe, Akiyoshi Nishiki, and Takeaki Naito: "Synthesis of Aminocyclohexitol via Carbon-Carbon Bond-Forming Radical Cyclization of Oxime Ether."Chem. Pharm. Bull.. 51. 100-103 (2003)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] Okiko Miyata, Kanami Muroya, Tomoko Kobayashi, Rina Yamanaka, Seiko Kajisa, Junko Koide, and Takeaki Naito: "Radical Cyclization in Heterocycle Synthesis. Part 13 : Sulfanyl Radical Addition-Cyclization of Oxime Ethers and Hydrazones Connected with Alkenes for Synthesis of Cyclic β-Amino Acids."Tetrahedron. 58. 4459-4479 (2002)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] Okiko Miyata, Ryuichi Iba, Jun Hashimoto, and Takeaki Naito: "A Convenient Route to the Furopyran Core of Dysiherbaine."Org. Biomol. Chem.. 1. 772-774 (2003)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] 宮部 豪人: "Synthesis of aminocyclohexitol via carbon-carbon bond-forming radical cyclization of oxime ether"Chem. Pharm. Bull.. 51(1). 100-103 (2003)

    • Related Report
      2002 Annual Research Report
  • [Publications] 宮田 興子: "Radical cyclization in heterocycle synthesis. 13. Sulfanyl radical addition-cyclization of oxime ethers and hydrazones connected with......"Tetrahedron. 58. 4459-4479 (2002)

    • Related Report
      2002 Annual Research Report
  • [Publications] 宮田 興子: "A convenient route to the furopyran core of dysiherbaine"Org. Biomol. Chem.. 1. 772-774 (2003)

    • Related Report
      2002 Annual Research Report
  • [Publications] 宮田興子: "Radical Cyclization in Heterocycle Synthesis. Part 10. A Concise Synthesis of (-)-Kainic Acid via Sulfanyl Radical Addition-Cyclization-Elimination Reaction"Tetrahedron. 56. 6199-6207 (2000)

    • Related Report
      2001 Annual Research Report
  • [Publications] 木口敏子: "Radical Cyclization in Heterocycle Synthesis. Part 9. A Novel Synthesis of Aminocyclitols and Related Compounds via Stannyl Radical Cyclization of Oxime"Tetrahedron. 56. 5819-5833 (2000)

    • Related Report
      2001 Annual Research Report
  • [Publications] 宮部豪人: "Asymmetric Synthesis of α-Amino Acids Based on Carbon Radical Addition to Glyoxylic Oxime Ether"J. Org. Chem.. 65. 176-185 (2000)

    • Related Report
      2001 Annual Research Report
  • [Publications] 内藤猛章: "Radical Cyclization of Oxime Ethers Derived from Monosaccharides Aiming at the Synthesis of Dysiherbaine and Related Stereoisomers"Heterocycles. 53. 2611-2615 (2000)

    • Related Report
      2001 Annual Research Report
  • [Publications] 内藤猛章: "Heteroatom Radical Addition-Cyclization and Its Synthetic Application"Heterocycles. 50(1). 505-541 (1999)

    • Related Report
      2000 Annual Research Report
  • [Publications] 宮部豪人: "Alkylative Amination of Aldehydes via Carbon-Carbon Bond Formation Based on Radical Addition to Carbon-Nitrogen Double Bond"Tetrahedron. 55. 11209-11218 (1999)

    • Related Report
      2000 Annual Research Report
  • [Publications] 宮部豪人: "Carbon Radical Addition to Glyoxylic Oxime Ether via Iodine Atom-Transfer Process"Synlett. 4. 465-467 (1999)

    • Related Report
      2000 Annual Research Report
  • [Publications] 内藤猛章: "Radical Cyclization in Heterocycle Synthesis 6.A New Entry to Cyclic Amino Alcohols via Stannyl Radical Cyclization of Oxime Ethers Connected with Aldehydes or Ketones"J.Org.Chem.. 64(6). 2003-2009 (1999)

    • Related Report
      2000 Annual Research Report

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Published: 2000-04-01   Modified: 2016-04-21  

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