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Development and Application of Novel Histamine H_3 agonist Imifuramine

Research Project

Project/Area Number 11672127
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeSingle-year Grants
Section一般
Research Field Chemical pharmacy
Research InstitutionOsaka University of Pharmaceutical Sciences

Principal Investigator

KURIHARA Takushi  Osaka University of Pharmaceutical Sciences, Prof., 薬学部, 教授 (90067281)

Co-Investigator(Kenkyū-buntansha) YAMATODANI Atsushi  Osaka University, Faculty of Medicine, Prof., 医学部, 教授 (30116123)
HARUSAWA Shinya  Osaka University of Pharmaceutical Sciences, Ass. Prof., 薬学部, 助教授 (90167601)
Project Period (FY) 1999 – 2002
Project Status Completed (Fiscal Year 2002)
Budget Amount *help
¥2,900,000 (Direct Cost: ¥2,900,000)
Fiscal Year 2002: ¥600,000 (Direct Cost: ¥600,000)
Fiscal Year 2001: ¥600,000 (Direct Cost: ¥600,000)
Fiscal Year 2000: ¥600,000 (Direct Cost: ¥600,000)
Fiscal Year 1999: ¥1,100,000 (Direct Cost: ¥1,100,000)
Keywordshistamine / H_3 / H_4 / receptor / agonist / antagonist / imidazole / imifuramine / レセプター / C-ヌクレオシド / コンホメーション
Research Abstract

Synthetic studies of imidazole C-nucleoside derivatives and their application to novel histamine H_3- and H_4-ligands are described, in which the following items are covered. 1) Stereoselective synthesis of imidazole C-nucleosides via diazafulvene intermediates. 2) Synthesis of tetrahydrofuranylimidazoles using efficient use of a PhSe group and its application to novel histamine H_3-ligands. 3) Histamine H_3- and H_4-agonistic activities of imifuramine derivatives. 4) Efficient synthesis of imifuramine and its stereoisomer via diazafulvene intermediates. 5) Difference between diazafulvene cyclization and intramolecular Mitsunobu reaction of 1,4-diols.

Report

(5 results)
  • 2002 Annual Research Report   Final Research Report Summary
  • 2001 Annual Research Report
  • 2000 Annual Research Report
  • 1999 Annual Research Report
  • Research Products

    (22 results)

All Other

All Publications (22 results)

  • [Publications] T.Hashimoto: "A Selective Human H_4-Rccepcor Agonist : (-)-2-Cyano-1-methyl-3-{(2R,SR)-5-[1H-imidazol-4(5)-yl]tetrahydrofuran-2-yl}methylguanidine"J. Med. Chem.. (in press). (2003)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] 春沢信哉: "総合論文:イミダゾールC-ヌクレオシド誘導体の合成研究とヒスタミンH_3およびH_4リガンドへの応用"有機合成化学協会誌. 61. 682-693 (2003)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] S.Harusawa: "Efficient Synthesis of trans-or cis-4(5)-(5-Aminomethyl-tetrahydrofuranyl)imidazoles via Diazafulvene Intermediates : Synthetic Approach"Chem.Pharm.Bull.. 51. 832-837 (2003)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] S.Harusawa: "Synthesis of (±)-trans-or cis-(5-Aminomethyltetrahydrofuranyl)imidazole by Mitsunobu Cyclization : Synthetic Studies toward Novel Histamine H_3 or"Chem.Pharm.Bull.. 51. 325-329 (2002)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] S.Harusawa: "An Efficient and Convenient Synthesis of 4-Vinylimidazoics Using a Novel Horner-Wadsworth-Emmons (HME) Reagent : Synthetic Studies Toward Novel"Synthesis. 1072-1078 (2002)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] L.Araki: "Synthesis of 4(5)-(α-D-Xylofuranosyl)imidazole Starting from L-Arabinose : Mitsunobu Cyclization via C4'-Oxyphosphonium Intermediate"Heterocycles. 55. 1907-1917 (2001)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] L. Araki: "Synthesis of Cis- or Trans-2,4-Disubstituted Tetrahydrofurans Bearing Amino and Imidazole Groups by Efficient Use of the Modified or Standard Mitsunobu"Heterocycles. 55. 889-903 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] S. Harusawa: "Stereoselective Synthesis of 4(5)-[(2S,3S)-and (2R,3R)-3-Aminotetrahydrofuran-2-yl]imidazoles 〜"Heterocycles. 53. 2739-2751 (2000)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] L. Araki: "4(5)-[5'-Amino-5'-deoxy-α-arabinofuranosyl]imidazole and its S'-derivatives Using Modified Mitsunobu Cyclization: Synthetic Studies Toward Novel"Heterocycles. 53. 1957-1973 (2000)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] S. Harusawa: "Synthesis of 4(5)-[5-(Aminomethyl)-tetrahydrofuran-2-yl or 5-(Aminomethyl)- 〜"J. Org. Chem.. 64. 8608-8615 (1999)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] S. Harusawa: "Synthesis of Imifuramine and its Stereoisomers Exhibiting Histamine H3-Agonistic Activity"Tetrahedron Lett.. 40. 2561-2564 (1999)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] Shinya Harusawa: "An efficient and convenient synthesis of 4-vinylimidazoles using a novel Horner-Wadsworth-Emmons (HWE) Reagent : Synthetic Studies towardnovel histamine〜"Synthesis. 8. 1072-1078 (2002)

    • Related Report
      2002 Annual Research Report
  • [Publications] Shinya Harusawa: "Synthesis of (±)-trans or cis-(5-aminomethyltetrahydrofuranyl)imidazole by Mitsunobu cyclization : synthetic studies toward novel histamine H_3 or H_4-ligands"Chem. Pharm. Bull.. 51・3. 325-329 (2003)

    • Related Report
      2002 Annual Research Report
  • [Publications] Takeshi Hashimoto: "A selective human H4-receptor agonist ; (-)-2-Cyanao-1-methyl-3-{(2R,5R)-5-[1H-imidazole-4(5)-yl]tetrahydrofuran-2-yl}methylguanidine"J. Med. Chem.. (in press). (2003)

    • Related Report
      2002 Annual Research Report
  • [Publications] 春沢信哉: "イミダゾールC-ヌクレオシド誘導体の合成研究とヒスタミンH3及びH4リガンドへの応用"有機合成協会誌. (in press). (2003)

    • Related Report
      2002 Annual Research Report
  • [Publications] Lisa Araki: "Synthesis of 4(5)-(α-D-Xylofuranosyl)imidazole Starting from L-Arabinose : Mitsunobu Cyclization via C4'-Oxyphosphonium Intermediate-"Heterocycles. 55・10. 1907-1917 (2001)

    • Related Report
      2001 Annual Research Report
  • [Publications] Lisa Araki: "Synthesis of Cis-or Trans-2,4-Disubstituted Tetrahydrofurans Bearing Amino and Imidazole Groups by Efficient Use of the Modified or Standard Mitsunobu Cyclization"Heterocycles. 55・5. 889-903 (2001)

    • Related Report
      2001 Annual Research Report
  • [Publications] Shinya Harusawa: "Histamine Research in the New Millenium"ELSEVIER SCIENCE B.V.. 521 (2001)

    • Related Report
      2001 Annual Research Report
  • [Publications] Lisa Araki: "Synthesis of 4(5)-[5'-Amino-5'-deoxy-α-L-arabinofuranosyl) imidazole and its 5'-derivatives using modified Mitsunobu cyclization :"Heterocycles. 53・9. 1957-1973 (2000)

    • Related Report
      2000 Annual Research Report
  • [Publications] Shinya Harusawa: "Stereoselective synthesis of 4(5)-[(2S,3S)- and (2R,3R)-3-aminotetrahydrofuran-2-yl) imidazoles Using Modified and Standard Mitsunobu Cyclizations :"Heterocycles. 53・12. 2739-2751 (2000)

    • Related Report
      2000 Annual Research Report
  • [Publications] Shinya Harusawa: "Synthesis of 4(5)-[5-(Aminomethyl)tetrahydrofuran-2-yl-or 5-(Aminomethyl)-2,5-dihydrofuran-2-yl]imidazoles by Efficent Use of a PhSe Group : Application to Novel"Tetrahedron Letters. 40・13. 2561-2564 (1999)

    • Related Report
      1999 Annual Research Report
  • [Publications] Shinya Harusawa: "Synthesis of Imifuramine and Its Stereisomers Exhibiting Histamine H_3-Agonistic Activity"The Journal of Organic Chemistry. 64・23. 8608-8615 (1999)

    • Related Report
      1999 Annual Research Report

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Published: 1999-04-01   Modified: 2016-04-21  

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