2000 Fiscal Year Final Research Report Summary
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
| Project/Area Number |
10672004
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| Research Category |
Grant-in-Aid for Scientific Research (C)
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| Allocation Type | Single-year Grants |
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| Section | 一般 |
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| Research Field |
Chemical pharmacy
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| Research Institution | MEIJI PHARMACEUTICAL UNIVERSITY |
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Principal Investigator |
KITAHARA Yoshiyasu MEIJI PHARMACETICAL UNIVERSITY, FACULTY OF PHARMACY, ASSOCIATE PROFESSOR, 薬学部, 助教授 (70114460)
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| Co-Investigator(Kenkyū-buntansha) |
SAITO Naoki MEIJI PHARMACETICAL UNIVERSITY, FACULTY OF PHARMACY, ASSOCIATE PROFESSOR, 薬学部, 講師 (80142545)
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| Project Period (FY) |
1998 – 2000
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| Keywords | pyrroloacridine / alkaloid / polycyclic heteroaromatic compound / marine natural product / total synthesis |
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| 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.
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Research Products
(2 results)
