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1989 Fiscal Year Final Research Report Summary

SYNTHETIC STUDIES ON BIOLOGICALLY ACTIVE TRYPTOPHAN METABOLITES.

Research Project

Project/Area Number 62470134
Research Category

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

Allocation TypeSingle-year Grants
Research Field Chemical pharmacy
Research InstitutionChiba University

Principal Investigator

HINO Tohru  Chiba Univ. Fac. Pharm. Sci. Prof., 薬学部, 教授 (10009160)

Co-Investigator(Kenkyū-buntansha) KAWATE Tomohiko  Chiba Univ., Fac. Pharm. Sci. Res. Assistant., 薬学部, 教務職員 (50195111)
NAKAGAWA Masako  Chiba Univ., Fac. Pharm. Sci. Assoc. Prof., 薬学部, 助教授 (40009171)
Project Period (FY) 1987 – 1989
KeywordsTryptophan / Eudistomin / beta-Carboline / Pictet-Spengler reaction / Oxathiazepine / D-Cystein / Marine natural products / Propargyl alcohol Co-complex
Research Abstract

1. Eudistomins. Marine alkaloids, eudistomin H, I, and P (1) have been synthesized from tryptamine and proline. Eudistomine C, F. L and debromoeudistomin L (2) which have a oxathiazepine ring and a tetrahydro-B- carboline ring and display anti-virus activity, have been synthesized as the first time from N-hydroxytryptamine and D-cysteinal.
2. Flustramines : 3a-(1,1-dimethylpropargyl)pyrrolo 2,3-b indole (3) has been prepared by the reaction of tryptamine carbamate and propargylalcolhol Co-complex in the presence of a Lewis acid.
3. The 4,5,6-tribromo-3-indoleacetamide (4) which is the indole moiety of chartelline, was prepared from the cyclic tautomer of 3-indoleacetamide.
4.12alpha- and 12beta-Fumitremorgin C (5) has been prepared from the intermediate to fumitremorgin B.
5. Optically active 1-substituted-1 2,3,4-tetrahydro-beta-carbolines (6) have been prepared by the asymmetic reduction of 1-substituted-3,4-dihydro-beta-carbolines with moderate optical purity.

  • Research Products

    (25 results)

All Other

All Publications (25 results)

  • [Publications] 古田土真一: "Total synthesis of(+)-fumitremorgin B,its epimeric isomers,and demethoxy derivatives." Tetrahedron. 44. 359-377 (1988)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] 中川昌子: "New avidence for the presence of a spiroigdolenine intermediate in Pictet-Spengler reaction of Nb-hydroxytryptamine." J.C.S.Chem.Commun.463-464 (1988)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] 小林淳一: "Eudistomin derivatives,novel phosphoesterase inhibitors:synthesis and relative activity." J.Pharm.Pharmacol.40. 62-63 (1988)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] 中川昌子: "Synthetic approaches fumitremorgins.Synthesis of optically pure pentacyclic ring systems,and their oxidation at ring C" Chem.Pharm.Bull.,. 37. 23-32 (1989)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] 日野亨: "A synthesis of so-called fumitremorgin C" Tetrahedron. 45. 1941-1944 (1989)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] 中川昌子: "Total synthesis of(-)-eudistomin L and(-)-debromoeudistomin L" J.Am.Chem.Soc.111. 2721-2722 (1989)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] 日野亨: "1-(1-Pyrrolin-2-yl)-β-carbolines.Synthesis of eudistomin H,I,andP." Chem.Pharm.Bull.37. 2596-2600 (1989)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] 劉進軍: "The Pictet-Spengler reaction of Nb-hydroxytryptamines and cysteinals.Isolation of tetracyclic intermediates and formation of β-carbolines."

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] 中川昌子: "The Nicholas reaction of indoles.Propargylation of indoles with(propargyl)-dicobalt hexacarbonyl cations." Heterocycles. 30. 451-462 (1990)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] 日野亨: "2-Hydroxy-1-substituted-1,2,3,4-tetrahydro-β-carbolines.The Pictet-Spengler reaction of N-hydroxytryptamine with aldehyde." Chem.Pharm.Bull.38. 59-64 (1990)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] 劉進軍: "Total synthesis of(-)-eudistomin F." Heterocycles,accepted. (1990)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] 日野亨: "Reactions of the cyclic tautomer of 3-indoleacetamides.Synthesis of N-methyl-4,5,6-tribromo-3-indoleacetamide." Chem.Pharm.Bull.in preparation.

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] 日野亨(A.Brossi,Ed): "The Alkaloids Vol.34 pp1-75 Chemistry and reactions of cyclic tautomers of tryptamines and tryptophans" Academic Press, 410 (1988)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] S.Kodato: "Total synthesis of (+)-fumitremorgin B, its epimeric isomers, and demethoxy derivatives" Tetrahedron, 44, 359-377 1988.

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] M.Nakagawa: "New evidence for the presence of a spiroindolenine intermediate in Pictet-Spengler reaction of Nb-hydroxytryptamine" J.C.S.Chem. Commun. 463-464.1988.

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] J.Kobayashi: "Eudistomin derivative, novel phospho-esterase inhibitors: synthesis and relative activity." J.Pharm.Pharmacol. 40.62-63, 1988.

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] M.Nakagawa: "Synthetic approaches to fumitremorgins. Synthesis of optically pure pentacyclic ring systems, and their oxidation at ring" Chem. Pharm. Bull. C. 37, 23-32, 1989.

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] T.Hino: "A synthesis of so-called fumitremorgin C" Tetrahedron, 45, 1941-1944,1989.

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] M.Nakagawa: "Total synthesis of (-)-eudistomin L and (-)-debromoeudistomin L" J. Am. Chem. Soc. 111,2721-2722,1989.

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] T.Hino: "1-(1-Pyrrolin-2-yl)-beta-carbolines. Synthesis of eudistsomin H, I, and P." Chem. Pharm. Bull. 37, 2596-2600,1989.

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] J.Liu: "The Pictet-Spengler reaction of Nb-hydroxy-tryptamines and cysteinals. Isolation of tetracyclic intnermediates and formation of beta-carbolines." Tetrahedron, 45, 7729-7742, 1989.

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] M.Nakagawa: "The Nicholas reaction of indoles. Propargylation of indoles with (propargyl) dicobalt hexacarbonyl cation." Heterocycles, 30, 451-462,1990.

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] T.Hino: "2-Hydroxy-1-substituted-1,2,3,4-tetrahydro-beta-carbolines. The Pictet-Spengler reaction of N-hydroxytryptamine with aldehydes." Chem. Pharm. Bull., 38, 59-64,1990.

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] J.Liu: "Total synthesis of (-)-eudisstomin F." Heterocycles.

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] T.Hino: "Reaction of the cyclic tautomer of 3-indoleacetamide. Synthesis of N-methyl-4,5,6-tribromo-3-indoleacetamide." Chem.Pharm.Bull.,.

    • Description
      「研究成果報告書概要(欧文)」より

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Published: 1993-03-26  

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