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Study on the Synthesis of Nitrogen Heterocycles Relsted to the Drugs of Parkison's Disease

Research Project

Project/Area Number 11672115
Research Category

Grant-in-Aid for Scientific Research (C)

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

Principal Investigator

SANO Takehiro  Showa Pharmaceutical Universit Professor, 薬学部, 教授 (00077520)

Co-Investigator(Kenkyū-buntansha) SAITOH Toshiaki  Showa Pharmaceutical Universit Research Associate, 薬学部, 助手 (00286882)
HORIGUHI Yoshie  Showa Pharmaceutical Universit Associate Professor, 薬学部, 助教授 (70190254)
戸田 潤  昭和薬科大学, 薬学部, 教授 (90188756)
Project Period (FY) 1999 – 2000
Project Status Completed (Fiscal Year 2001)
Budget Amount *help
¥2,000,000 (Direct Cost: ¥2,000,000)
Fiscal Year 2000: ¥500,000 (Direct Cost: ¥500,000)
Fiscal Year 1999: ¥1,500,000 (Direct Cost: ¥1,500,000)
Keywordsterahydroquinoline / parkinson's disease / pummerer reaction / 1,2,3,4-tetrahydroquinoline / benzoazepine / benzothiazine / tetrahydroisoquinoline / tetrahydroquinoline / trifluoroacetic anhydride / sulfoxide / synthesis
Research Abstract

In order to contribute to the development of biological study of tetrahydroisoquinolines, amines present in human brain, we have investigated the development of method synthesizing the tetrahydroisoquinolines and their analogs. Some tetrahydroisoquinolines are known to be a toxin which induces Parkinson's disease, while 1-methyl-1, 2, 3, 4-tetrahydroisoquinoline protects the parkinsonism induced by these toxins. The synthesis of these compounds was achieved by applying Pummerer-type reaction. The method consists in the nuceophilic substitution reaction of aromatic ring to the sulfoxide mediated carbocation, was discovered to be highly efficient and widely applicable for synthesizing the variously substituted nitrogen heterocycles, 1, 2, 3, 4-tetrhahydroisoquinoline and benzoazepines.

Report

(3 results)
  • 2001 Final Research Report Summary
  • 2000 Annual Research Report
  • 1999 Annual Research Report

Research Products

(24 results)

All Other

All Publications (24 results)

  • [Publications] T.Sano, et al.: "A Novel Synthesis of 1,2,3,4-Tetrahydroquinolines via Pummerer-Type Reaction of N-Aryl-N-[(phenylsulfinyl)propyl]formamide"Chem. Pharm. Bull.. 47. 1269-1275 (1999)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] T.Sano, et al.: "A Chiral Synthesis of Four Stereoisomers of 1,3-Dimethyl-1,2,3,4-tetrahydroisoquinoline, an Inducer of Parkinson-like Syndrome"Chem. Pharm. Bull.. 48. 91-98 (2000)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] T.Sano, et al.: "Synthesis of 4-ary1-2-methyl-1,2,3,4-tetrahydroisoquinolines via Pummerer-type cyclization of N-(aryl)methyl-N-methyl-2-aryl-2-(phenylsulfinyl)acetamides"Arkivoc. 1. 165-180 (2000)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] T.Sano, et al.: "Synthesis of Methoxy-2-quinolones via Pummerer-type Cyclization of N-Aryl-N-methyl-3-(phenylsulfanyl)propionamides"Chem. Pharm. Bull. 48. 1854-1861 (2000)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] T.Saitoh, et al.: "A Synthesis of 3-Phenyl-1,2,3,4-tetrahydroisoquinoline and 2,3,4,5-tetrahydro-1H-3-benzazepine via Pummerer-type Cyclization : The Enhancing Effect of Born Trifluoride Diethyl Etherate on the Cyclization"Chem. Pharm. Bull.. 49. 979-984 (2001)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] Y.Horiguchi, et al.: "Synthesis of 2,3,4,5-Tetrahydro-IH-2-benzazepines via Pummerer-type Cyclization of N-(Aryl)methyl-N-(3-phenylsulfinylpropyl)formamides"Heterocycles. 54. 967-984 (2001)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] J. Toda, M. Sakagami, and T. Sano.: "A Novel Synthesis of 1, 2, 3, 4-Tetrahydroquinolines via Pummerer-Type Reaction of N-Aryl-N- [(phenylsulfinyl)propyl]formamide"Chem. Pharm. Bull.. 47. 1269-1275 (1999)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] J. Toda, S. Matsumoto, T. Saitoh, and T. Sano: "A Chiral Synthesis of Four Stereoisomers of 1, 3-Dimethyl-1, 2, 3, 4-tetrahydroisoquinoline, an Inducer of Parkinson-like Syndrome"Chem. Pharm. Bull.. 48. 91-98 (2000)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] J. Toda, A. Sonobe, T. Ichikawa, T. Saitoh, Y. Horiguchi, and T. Sano: "Synthesis of 4-aryl-2-methyl- 1, 2, 3, 4-tetrahydroisoquinolines via Pummerer-type cyclization of Af-(aryl)methyl-Af-methyl-2-aryl-2-(phenylsulfmyl)acetamides"Arkivoc. 1. 165-180 (2000)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] J. Toda, M. Sakagami, Y. Goan, M. Simakata, T. Saitoh, Y. Horiguchi, and T. Sano: "Synthesis of Methoxy-2-quinolones via Pummerer-type Cyclization of N-Aryl-A/-methyl-3-(phenylsulfanyl)propionamides"Chem. Pharm. Bull.. 48. 1845-1861 (2000)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] J. Toda, T. Ichikawa, T. Saitoh, Y. Horiguchi, and T. Sano: "A Synthesis of 2, 3, 4, 5-tetrahydro- lH-3-benzazepines via Pummerer-type Cyclization of N-[2- (Aryl) ethyl] -H- [2 - (phenyl sulfinyl) ethy] formamides"Heterocycles. 52. 2009-2018 (2000)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] T. Saitoh, T. Ichikawa, Y. Horiguchi, J. Toda, and T. Sano: "A Synthesis of 3-Pheny-1, 2, 3, 4-tetrahydroisoquinoline and 2, 3, 4, 5-tetrahydro-1H-3- benzazepine via Pummerer-type Cyclization"Chem. Pharm. Bull.. 49. 979-984 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] Y. Horiguchi, T. Saitoh, S. Terakado, K. Honda, T. Kimura, J. Toda, and T. Sano: "Synthesis of 2, 3, 4, 5-Tetrahydro-1H-2-benzazepines via Pummerer-type Cyclization of N- (Aryl)methyl-A/-(3 -phenylsulfinylpropyl)formamides"Heterocycles. 54. 967-984 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] T. Sano: "Recent Advances in the Synthesis of Aromatic Condensed JV-Heterocycles Using Pummerer-type Intramolecular Cyclization Reaction"(in press). (2002)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] J.Toda, et al.,: "A Novel Synthesis of 1, 2, 3, 4-Tetrahydroquinolines via Pummerer-Type Reaction of N-Aryl-N-[(phenylsulfinyl)propyl] formamide,"Chem.Pharm.Bull.,. 47. 1269-1275 (1999)

    • Related Report
      2000 Annual Research Report
  • [Publications] J.Toda, et al.,: "A Chiral Synthesis of Four Stereoisomers of 1, 3-Dimethyl-1, 2, 3, 4-tetrahydroisoquinoline, an Inducer of Parkinson-like Syndrome,"Chem.Pharm.Bull.,. 48. 91-98 (2000)

    • Related Report
      2000 Annual Research Report
  • [Publications] J.Toda, et al.,: "Synthesis of 4-aryl-2-methyl-1, 2, 3, 4-tetrahydroisoquinolines via Pummerer-type cyclization N-(aryl) methyl-N-methyl-2-aryl-2-(phenylsulfinyl)acetamides,"Arkivoc,. 1. 165-180 (2000)

    • Related Report
      2000 Annual Research Report
  • [Publications] J.Toda, et al.,: "Synthesis of Methoxy-2-quinolones via Pummerer-type Cyclization of N-Aryl-N-methyl-3-(phenylsulfanyl) propionamides,"Chem.Pharm.Bull.,. 48. 1845-1861 (2000)

    • Related Report
      2000 Annual Research Report
  • [Publications] J.Toda, et al.,: "A Synthesis of 2, 3, 4, 5-tetrahydro-1 H-3-benzazepines via Pummerer-type Cyclization of N-[2-(Aryl) ethyl]-N-[2-(phenylsulfinyl) ethyl] formamides,"Heterocycles,. 52. 2009-2018 (2000)

    • Related Report
      2000 Annual Research Report
  • [Publications] Y.Horiguchi,: "Synthesis of 2, 3, 4, 5-Tetrahydro-1 H-2-benzazepines via Pummerer-type Cyclization of N-(Aryl) methyl-N-(3-phenylsulfinylpropyl) formamides"Heterocycles,. 53(in press). (2001)

    • Related Report
      2000 Annual Research Report
  • [Publications] 佐野武弘: "脳内アミン、1-メチルテトラヒドロイソキノリンのパーキンソン病治療薬としての可能性"有機合成協会誌. 57(2). 76-80 (1999)

    • Related Report
      1999 Annual Research Report
  • [Publications] T. Shinohara, et al: "A Synthesis of Some Trimethoxylated 1 ,2,3,4-tetrahydroisoquinoline Aikaloids via Pummerer Reaction of N-Trimethoxybenzyl-N-[2-phenylsulfinyl)ethyl]formamides"Heterocycles. 51(1). 119-120 (1999)

    • Related Report
      1999 Annual Research Report
  • [Publications] J. Toda, et al: "A Novel Synthesis of 1,2,3,4-Tetrahydroquinolines via Pummerer-type reaction of N-Acyl-N-aryl-2-(phenylsulfinyl)propylamine by Pummere Reaction"Chem. Pharm. Bull.. 47(9). 1269-1275 (1999)

    • Related Report
      1999 Annual Research Report
  • [Publications] J. Toda,et al: "A Chiral Synthesis of Four Stereoisomers of 1 ,3-Dimethyl- 1 ,2.3,4-tetrahydroisoquinoline, an inducer of Parkinson-like Syndrome"Chem. Pharm. Bull.. 48(1). 91-98 (2000)

    • Related Report
      1999 Annual Research Report

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Published: 1999-03-31   Modified: 2016-04-21  

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