| Project/Area Number |
07457523
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| Research Category |
Grant-in-Aid for Scientific Research (B)
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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 | Teikyo University |
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Principal Investigator |
IKEGAMI Shiro Teikyo University, Faculty of Pharm.Sci., Professor, 薬学部, 教授 (10119555)
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| Co-Investigator(Kenkyū-buntansha) |
AZUMAYA Isao Teikyo University, Faculty of Pharm.Sci., Research Associate, 薬学部, 助手 (50276755)
TAKAHASHI Hideyo Teikyo University, Faculty of Pharm.Sci., Research Associate, 薬学部, 助手 (10266348)
OHTAKE Hiro Teikyo University, Faculty of Pharm.Sci., Reserach Associate, 薬学部, 助手 (50256054)
MIYAZAKI Yoji Teikyo University, Faculty of Pharm.Sci., Research Associate, 薬学部, 助手 (70211597)
IIMORI Takamasa Teikyo University, Faculty of Pharm.Sci., Associate Professor, 薬学部, 助教授 (90246025)
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| Project Period (FY) |
1995 – 1996
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| Project Status |
Completed (Fiscal Year 1996)
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| Budget Amount *help |
¥7,300,000 (Direct Cost: ¥7,300,000)
Fiscal Year 1996: ¥1,600,000 (Direct Cost: ¥1,600,000)
Fiscal Year 1995: ¥5,700,000 (Direct Cost: ¥5,700,000)
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| Keywords | Isocarbacycline Analogue / Enediyne Compounds / Organolead Reagent / Ring Transformation / Decarboxylative Glycosidation / Clycosylene Orthoester / Reductive Glycosidation / Cyclophellitol / Glycosylene Orthoerste / Cyclophellitol / プロスタサイクリン / イソカルバサイクリン / 有機鉛化学 / α-1-アルケニルケトン / α-アルキニルケトン / ロジウム不斉触媒 / ロジウムカルベノイド / グリコシル化反応 |
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| Research Abstract |
The six independent subjects have been examined for past two research years and the successful resultes we obtained are summarized as follows.
1. The new and versatile synnthetic procedure for alpha- (E&Z) -alkenylkentones by emplying alkenyllead reagents has been extended to the preparation of alpha-alkynylketones. An applikation of this technique to the synthesis of 13,14-didehydroisocarbacycline has been used successuflly.
2. In order to clarify an affinity power of prostacycline analogues with a PGI_2 reseptor, an unexpectedly low potency of the analogues, 6-Isocarbacycline was reexamined. The analogue was successfully synthesized in the opteically active form.
3. A strong inducer of thrombomoduline would be a candidate for new antithrombotic agent. As 9-cis-Retionic acid has more potent activity than its trans isomer, several 9-cis-analogues fixed with cycloalkanes and heterocycles have been syntesized. The analogues with 5-membered rings exhibit an activity equivanlent to 9-cis-Retinoic acid.
4. In order to establish an efficient and versatile glycosylation reaction, a conceptionally different glycosylation based on decarboxylative glycosylation was investigate and the procedure gave good results in good yields and selectivity.
5. Orthoesters formed from 1-dehydrosugar and another sugar shoul be good resourses for glycosyl bond formation. Reductive cleavage of one of a C-O bond would afford the corresponding glycoside. An investigation gave an excellent result.
6. Stereochemically difined polyhydroxylated-cyclohexanones should be one of the most powerful syntheticintermediates for bioactive substances. Efficient and practical procedures for the ring-transformation from sugars to polyhydroxylated cyclohexanones were investigated and it wa established that the reactions proceed smoothly by using a catalytic amount of PdCl_2。
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