Regio- and Stereoselective Synthesis of Carbocyclic 2', 3'-Dideoxy-3'-fluoro Nucleosides as Potential Antiviral Agents
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概要
- 論文の詳細を見る
The synthesis and antiviral activity of racemic carbocyclic 2', 3'-dideoxy-3'-fluoro nucleosides are reported. Carbocyclic 2', 3'-dideoxy-3'-fluoro nucleosides were obtained from the 3-fluoro cyclopentane derivative 4,which was prepared by two methods. The SN2-displacement of the hydroxyl group of (±)-(1β, 2α, 3β, 4β)-4-acetamido-2-fluoro-3-hydroxycyclopentylmethyl acetate (1) with Ph_3P-I_2 followed by tin hydride reduction afforded the 3-fluoroamino alcohol derivative 3. Alternatively, the protected fluoroamino alcohol 3 was prepared by regio- and stereoselective bromo-fluorination of cis-4β-acetamidocyclopent-2-enemethyl acetate (5) with hydrogen fluoridepyridine/N-bromosuccinimide followed by tin hydride reduction to remove the bromine atom. Carbocyclic 2', 3'-dideoxy-3'-fluoroguanosine (14) thus obtained was moderately active against herpes simplex virus in vitro.
- 社団法人日本薬学会の論文
- 1994-02-15
著者
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安田 新
Research Center Asahi Glass Co. Ltd.
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高瀬 浩之
Exploratory Research Laboratories I Daiichi Pharmaceutical Co. Ltd.
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森澤 義富
Research Center Asahi Glass Co. Ltd.
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松村 靖
Research Center, Asahi Glass Co., Ltd.,
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中山 利明
Research Center, Asahi Glass Co., Ltd.,
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内田 啓一
Research Center, Asahi Grass Co., Ltd.,
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村上 要一
Exploratory Research Laboratories I, Daiichi Pharmaceutical Co., Ltd.,
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新子 省悟
Exploratory Research Laboratories I, Daiichi Pharmaceutical Co., Ltd.,
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池内 澄
Exploratory Research Laboratories I, Daiichi Pharmaceutical Co., Ltd.,
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長田 恭明
Exploratory Research Laboratories I, Daiichi Pharmaceutical Co., Ltd.,
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内田 啓一
Research Center Asahi Grass Co. Ltd.
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村上 要一
Exploratory Research Laboratories I Daiichi Pharmaceutical Co. Ltd.
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中山 太ニ
岡山大学薬学部薬剤学教室
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Matsumura Y
Asahi Glass Co. Ltd.
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Matsumura Yasushi
Fine Chemical Group Chemicals Company Asahi Glass Co. Ltd.
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新子 省悟
Exploratory Research Laboratories I Daiichi Pharmaceutical Co. Ltd.
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中山 太二
College Of Pharmacy Nihon University
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中山 利明
Research Center Asahi Glass Co. Ltd.
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池内 澄
Exploratory Research Laboratories I Daiichi Pharmaceutical Co. Ltd.
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長田 恭明
Exploratory Research Laboratories I Daiichi Pharmaceutical Co. Ltd.
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