| Project/Area Number |
62870085
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| Research Category |
Grant-in-Aid for Developmental Scientific Research
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| Allocation Type | Single-year Grants |
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| Research Field |
Chemical pharmacy
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| Research Institution | Chiba University |
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Principal Investigator |
ISHII Hisashi Chiba Univ. Fac. of Pharm. Scien. Professor, 薬学部, 教授 (70009166)
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| Co-Investigator(Kenkyū-buntansha) |
ISHIKAWA Tsutomu Res. Associate, 薬学部, 助手 (20114233)
HARAYAMA Takashi Assoc. Professor, 薬学部, 助教授 (30025712)
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| Project Period (FY) |
1987 – 1989
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| Project Status |
Completed (Fiscal Year 1989)
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| Budget Amount *help |
¥10,100,000 (Direct Cost: ¥10,100,000)
Fiscal Year 1989: ¥2,100,000 (Direct Cost: ¥2,100,000)
Fiscal Year 1988: ¥2,000,000 (Direct Cost: ¥2,000,000)
Fiscal Year 1987: ¥6,000,000 (Direct Cost: ¥6,000,000)
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| Keywords | Synthesis / Antitumor alkaloid / Chelerythrine / Propargyl ether / Claisen rearrangement / Furan ring formation / Furan ring cleavage / ベンゾ(C)フェテンスリジン / ファガリジン / ケリルビン / 抗腫瘍性 / シアノエチルピリジン / ケレリスリン型塩基 / オルトホルミルフェノール / フラン環の開裂 / ベンゾ[C]フェナンスリジン |
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| Research Abstract |
1)Claisen Rearrangement of Aryl propargyl ether in the Presence of CsF. Claisen rearrangement of primary propargyl ether in the presence of CsF afforded exclusively the arylfuran derivated. The reaction condition was examined in detail using beta-naphtol derivatives (1) : (a)the best solvent is diethylaniline; (b)CsF is essential. A generality of the reaction was investigated using the compound(2-4).
2)Cleavage of Arylfuran Ring. Oxidative cleavage of furan ring using derivative (5)was investigated. Consequently, successive treatment of 5 with a stoichiometric amount of OsO_4,NaIO_4, and aq. NaHCO_3 solution provided the desired salicylaldehyde (6) in a good yield.
3)Synthetic Studies on Chelerythrine (8, R=Me, R'=H) and the related compounds. The compound (7) was prepared by two routes using Claisen rearrangement in the presence of CsF and then, oxidatively cleaved to salicylaldehyde derivatives, which was converted to chelerythrine (8, R=Me, R'=H). Synthesis of phenolic base (8, R=Me, R'=OH) was also examined from the viewpoint of antitumor activity and the key intermediate was prepared in a high yield.
The biological assay of a various compounds including synthetic intermediates was under investigation.
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