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Potentiality of Alkylthiofuropyridone for Exploitation of Cerebrovascular Agents

Research Project

Project/Area Number 01571171
Research Category

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

Allocation TypeSingle-year Grants
Research Field Chemical pharmacy
Research InstitutionKobe Women's College of Pharmacy

Principal Investigator

NAITO Takeaki  Kobe Women's College of Pharmacy, Professor, 薬学部, 教授 (00068339)

Co-Investigator(Kenkyū-buntansha) MIYATA Okiko  Kobe Women's College of Pharmacy, Lecturer, 薬学部, 講師 (90102110)
KIGUCHI Toshiko  Kobe Women's College of Pharmacy, Lecturer, 薬学部, 講師 (70068344)
Project Period (FY) 1989 – 1990
Project Status Completed (Fiscal Year 1990)
Budget Amount *help
¥2,100,000 (Direct Cost: ¥2,100,000)
Fiscal Year 1990: ¥800,000 (Direct Cost: ¥800,000)
Fiscal Year 1989: ¥1,300,000 (Direct Cost: ¥1,300,000)
KeywordsSenile Dementia / Cerebrovascular Dementia / Alzheimer's Disease / Muscarinic Agonist / Alkylthiofuropyridone / Piperidine Alkaloid / Vincamine Alkaloid / ビンカアルカロイド
Research Abstract

Considering that both cerebrovascular agents and muscarinic agonists for the treatment for Alzheimer's disease have the substituted piperidine as a common key structural feature, we have investigated the development of new synthetic strategy for both medicinals employing the bicyclic heterocycles, alkylthiofuropyridone, as a synthon.
We first established an efficient synthetic route for a valuable synthon, alkylthiofuropyridone' via the route involving the reductive photocyclization of the alkylthio-enamides. Potentiality of the furopyridone has been evaluated by the synthetically useful reactions involving three functional groups, alkylthio, enolether, and lactam carbonyl groups which have provided a novel carbon-carbon bond formation and ring transformation reactions.
Reductive photocyclization of alkylthio-enamides, prepared from the carboxylic acid, primary amine, and furoyl chloride, in the presence of sodium borohydride proceeded smoothly to give two types of alkylthiofuropyridones. Alkylation of the furopyridone via the lactam carbonyl-enolate gave the 3, 4-disubstituted piperidines which were efficiently converted into the analogues of the known muscarinic agonists and also into the biologically active alkaloids, tecomanine (hypoglycemic activity), quinine (antimalarial agent), emetine (antiamebic agent), and ajmalicine (adrenergic blocking agent). Elimination-addition reaction of another furopyridone gave the 3, 3-disubstituted piperidines, some of which have proved common intermediates for the synthesis of eburnamine-vincamine alkaloids, eburnamonine (cerebrovascular agent) and cuanzine (antiarrhythmic, vasodilatory, and antihypertensive activties).

Report

(3 results)
  • 1990 Annual Research Report   Final Research Report Summary
  • 1989 Annual Research Report
  • Research Products

    (13 results)

All Other

All Publications (13 results)

  • [Publications] 内藤 猛章: "A Novel Total Synthesis of (±)ーAjmalicine" Heterocycles. 24. 2117-2120 (1986)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1990 Final Research Report Summary
  • [Publications] 内藤 猛章: "An Efficient Synthesis of (±)ーEmetine Using α,βーUnsaturated Lactams as a Michael Acceptor" Chem.Pharm.Bull.,. 34. 3530-3533 (1986)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1990 Final Research Report Summary
  • [Publications] 内藤 猛章: "Alkaloid Synthesis Using Furopyridone as SynthonーーSynthesis of Key Intermediates for the Synthesis of (±)ーQuinine,(±)ーAjmalicine,and (±)ー7ーDemethyltecomanineーー" Heterocycles. 27. 1321-1324 (1988)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1990 Final Research Report Summary
  • [Publications] 内藤 猛章: "Intramolecular Cyclization of Methylthiofuropyridone" Heterocycles. 29. 459-462 (1989)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1990 Final Research Report Summary
  • [Publications] 内藤 猛章: "Photocyclisation of Enamides.Part 29.A General Strategy for the Synthesis of Ipecac and Heteroyohimbine Alkaloids." J.Chem.Soc.,Perkin Trans.1,. 1271-1280 (1990)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1990 Final Research Report Summary
  • [Publications] 内藤 猛章: "Photocyclization of Enamides.Part 32.Alkaloid Synthesis Using Furopyridone as a Synthon.Synthesis of Key Intermediates for the Synthesis of (±)ーQuinine,(±)ーAjmalicine,and (±)ー7ーDemethyltecomanine" Chem.Pharm.Bull.,. 38. 2419-2423 (1990)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1990 Final Research Report Summary
  • [Publications] 内藤 猛章: "Alkaloid Synthesis Using Furopyridone as SynthonーSynthesis of Key Intermediates for the Syntheses of (±)ーQuinine,(±)ーAjmalicine,and (±)ー7ーDemethyltecomanineーー" Heterocycles. 27. 1321-1324 (1988)

    • Related Report
      1990 Annual Research Report
  • [Publications] 内藤 猛章: "Intramolecular Cyclization of Methylthiofuropyridone" Heterocycles. 29. 459-462 (1989)

    • Related Report
      1990 Annual Research Report
  • [Publications] 内藤 猛章: "Photocyclization of Enamides.Part 32.Alkaloids Synthesis Using Furopyridone as SynthonーーSynthesis of Key Intermediates for the Synthesis of (±)ーQuinine,(±)ーAjmalicine,and (±)ー7ーDemethyltecomanineーー" Chem.Pharm.Bull.38. 2419-2423 (1990)

    • Related Report
      1990 Annual Research Report
  • [Publications] 内藤 猛章: "Photocyclisation of Enamides.Part 29.A General Strategy for the Synthesis of Ipecac and Heteroyohimbine Alkaloids" J.Chem.Soc.,Perkin Trans 1. 1271-1280 (1990)

    • Related Report
      1990 Annual Research Report
  • [Publications] 内藤猛章: "Alkaloid synthesis Using Furopyridone as Synthon--Synthe-sis of Key Intermediates for the Syntheses of(±)-Quinine.(±)-Ajmalicine,and(±)-7-Demethyltecomanine--" Heterocycles. 27. 1321-1324 (1988)

    • Related Report
      1989 Annual Research Report
  • [Publications] 内藤猛章: "Intramolecular Cylization of Methylthiofuropyridones" Heterocycles. 29. 459-462 (1989)

    • Related Report
      1989 Annual Research Report
  • [Publications] 内藤猛章: "Photocyclization of Enamides.Part 32.Alkaloids Synthesis Using Furopyridone as Synthon--Synthesis of Key Intermediates for the Synthesis of(±)-Quinine,(±)-Ajmalicine,and(±)-7-Demethyltecomanine--" Chem.Pharm.Bull.

    • Related Report
      1989 Annual Research Report

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Published: 1989-04-01   Modified: 2016-04-21  

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