• Search Research Projects
  • Search Researchers
  • How to Use
  1. Back to previous page

ピロロ〔2,3,4-kl]アクリジン骨格を有する生理活性天然物の合成

Research Project

Project/Area Number 10672004
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeSingle-year Grants
Section一般
Research Field Chemical pharmacy
Research InstitutionMEIJI PHARMACEUTICAL UNIVERSITY

Principal Investigator

KITAHARA Yoshiyasu  MEIJI PHARMACETICAL UNIVERSITY, FACULTY OF PHARMACY, ASSOCIATE PROFESSOR, 薬学部, 助教授 (70114460)

Co-Investigator(Kenkyū-buntansha) SAITO Naoki  MEIJI PHARMACETICAL UNIVERSITY, FACULTY OF PHARMACY, ASSOCIATE PROFESSOR, 薬学部, 講師 (80142545)
Project Period (FY) 1998 – 2000
Project Status Completed (Fiscal Year 2000)
Budget Amount *help
¥1,300,000 (Direct Cost: ¥1,300,000)
Fiscal Year 2000: ¥600,000 (Direct Cost: ¥600,000)
Fiscal Year 1999: ¥700,000 (Direct Cost: ¥700,000)
Keywordspyrroloacridine / alkaloid / polycyclic heteroaromatic compound / marine natural product / total synthesis / 芳香族化合物
Research Abstract

In recent years a series of structurally related and biologically active polycyclic aromatic alkaloids possessing pyrido [2,3,4-kl] acridine or pyrrolo [2,3,4-kl] acridine skeleton have been isolated from marine organisms. We achieved synthesis of the alkaloids including iminoquinoline-quinone structure, e.g. 11-hydroxyascididemin and kuanoniamine A.In this research project we have studied total synthesis of meridine and cystodamine, and synthesis of pyrrolo [2,3,4-kl]- acridine (1) and benzo [b] pyrrolo [4,3,2-de][1,10] phenanthrolin-8 (11H)-one (2), a common skeleton of plakinidine A-C.
(a) Meridine and cystodamine were synthesized by using hetero Diels-Alder reaction between 4-methoxy-(or 4-chloro-) 5,8-quinolinedione and 2-nitrocinnamaldehyde dimethylhydrazone as a key step.
(b) 7-methylbenzo [b][1,10] phenanthrolin-4 (1H)-one (3) was obtained from o-aminoacetophenone and o-bromonitrobenzene. However we found that synthesis of 2 from 3 will be difficult.
(c) Pyrrolo [2,3,4-kl] acridin-1 (2H)-one possessing the same skeleton as 1 was synthesized from o-Aminoacetophenone and m-bromonitrobenzene via 2-acetylpyrrolo [2,3,4-kl] acridin-1 (2H)-one (4). 6,11-dihydrobenzo [b] pyrrolo [4,3,2-de][1,10] phenanthroline-5, 8-dione possessing the same skeleton as 2 was synthesized from 4.

Report

(4 results)
  • 2000 Annual Research Report   Final Research Report Summary
  • 1999 Annual Research Report
  • 1998 Annual Research Report
  • Research Products

    (2 results)

All Other

All Publications (2 results)

  • [Publications] 北原嘉泰,久保陽徳 他: "Synthesis of Meridine, Cystodamine, and Related Compounds Including Iminoquinolinequinone Structure"Tetrahedron Letters. 54. 8421-8432 (1998)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] Kitahara, Y. ; Tamura, F. ; Nishimura, M. ; Kubo, A.: "Synthesis of Meridine, Cystodamine, and Related Compounds Including Iminoquinolinequinone Structure"Tetrahedron Letters. 54 (29). 8421-8432 (1998)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2000 Final Research Report Summary

URL: 

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

Information User Guide FAQ News Terms of Use Attribution of KAKENHI

Powered by NII kakenhi