2003 Fiscal Year Final Research Report Summary
Synthetic investigation of lead compounds possessing antitutor and antiviral activities
| Project/Area Number |
13672226
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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 | Health Sciences University of Hokkaido |
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Principal Investigator |
ISHIKURA Minoru Health Sciences University of Hokkaido, Faculty of Pharmaceutical Sciences, Professor, 薬学部, 教授 (10146011)
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| Co-Investigator(Kenkyū-buntansha) |
HASUNUMA Miyako Health Sciences University of Hokkaido, Faculty of Pharmaceutical Sciences, Assistant, 薬学部, 助手 (50364253)
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| Project Period (FY) |
2001 – 2003
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| Keywords | indolylborate / cross-coupling reaction / indole alkaloid / ABH / carbocyclic nucleoside / cycloaddition / aziridine / oxirane |
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| Research Abstract |
In this project, the development of synthetic appliobilities of indolylborate and 2-azabicyclo[2.2.1]hept-5-en-3-one (ABH) as a valuable synthon of indole alkaloids and carbocyclic nucleoside derivatives was investigated.
1. Synthetic study of strychnos and uleine alkaloids through tandem cyclization-cross-coupling reaction with indolylborate
Conversion of 2-vinylindole derivatives, readily available from the tandem cyclization-cross-coupling reaction of indolylborate wirh (2-bromoprop-2-enyl)pentyl-3-nylamine in a one-pot manner, to strychnos indole alkaloid was investigated.
2. Novel approach to the construction of carbazole derivatives through intramolecular alkyl migration reaction.
Investigation of intramolecular alkyl migration reaction in indolylborate possessing an electrophilic center was carried out, which provided novel methodology for the construction of carbazole derivatives.
3. Synthesis of novel carbocyclic nucleoside derivatives by the use of 2-azabicyclo[2.2.1]hept-5-en-3-one (ABH)
Cycloaddition reaction toward the double bond of ABH proceeded stereoselectively to provide the exo-adduct. This reaction was used for the construction of novel carbocyclic nucleoside fused with cyclopropane, aziridine and oxirane rings at the 2',3' position of carbocyclic nucleoside derivatives.
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