Synthesis of 5-Amino-1-(3'-deoxy-β-D-ribofuranosyl)-4-imidazolethiocarboxamide
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概要
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As an interesting analog of thio-AICA-riboside (5-amino-1-β-D-ribofuranosyl-4-imidazolethiocarboxamide), 3'-deoxy-thio-AICA-riboside (XV) was prepared. 5'-Acetyl-AICA-riboside (X) synthesized from Ip-AICA-riboside (VIII) was allowed to react with triphenylphosphine and carbon tetrachloride to give, after ammoniacal treatment, the 3'-chloro derivative (XI). Treatment of the compound XI with alkali gave a epoxide derivative (XVI). Hydrogenation of XI followed by acetylation gave 2', 5'-diacetyl derivative (XIII). When XIII was thiolated with phosphorus pentasulfide, 2', 5'-di-O-acetyl-thio-AICA-riboside (XIV) formed. Deacetylation of XIV with ammonia furnished XV, which did not show any significant antitumor activity.
- 公益社団法人日本薬学会の論文
- 1976-09-25
著者
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山崎 晤弘
Central Research Laboratories, Ajinomoto Co., Inc.
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山崎 晤弘
Central Research Laboratories Ajinomoto Co. Inc.
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三芳 毅
Central Research Laboratories, Ajinomoto Co., Inc.
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須崎 茂男
Central Research Laboratories, Ajinomoto Co., Inc.
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三芳 毅
Central Research Laboratories Ajinomoto Co. Inc.
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須崎 茂男
Central Research Laboratories Ajinomoto Co. Inc.
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- Synthesis of 5-Amino-1-(3'-deoxy-β-D-ribofuranosyl)-4-imidazolethiocarboxamide
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