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2001 Fiscal Year Final Research Report Summary

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)
Project Period (FY) 1999 – 2000
Keywordsterahydroquinoline / parkinson's disease / pummerer reaction / 1,2,3,4-tetrahydroquinoline / benzoazepine / benzothiazine
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.

  • Research Products

    (14 results)

All Other

All Publications (14 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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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

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Published: 2003-09-17  

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