Alteration of 5-Chloropyrimidine Nucleosides in Alkaline Media
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概要
- 論文の詳細を見る
5-Chlorouridine (III), 5-chlorocytidine (IV), and 5-chloro-1-β-D-arabinofuranosylcytosine (VIII) were obtained in a yield of 61%, 61%, and 11.2% respectively by reaction of pyrimidine nucleosides with N-chlorosuccinimide. 2,2'-Anhydro-5-chloro-1-β-D-arabinofuranosyl cytosine (XI) was prepared in a yield of 53% by reaction of IV with Vilsmeier-Haack reagent. 5-Chloropyrimidine nucleosides (III, 5-chloro-1-β-D-arabinofuranosyluracil (VII), IV, and VIII) were found to degrade in aqueous alkali (1 N NaOH) at 50° via deamination or 6,2' (or 5')-anhydro open-chain ureido compounds. IV was more readily degraded in 0.3 N KOH at 37° than non-chlorinated (II). An unique reaction was that the treatment of XI with 0.1 N NaOH at room temperature afforded 2,2'-anhydro-5-hydroxy-1-β-D-arabinofuranosylcytosine (XII) without splitting the anhydro bond.
- 公益社団法人日本薬学会の論文
- 1975-01-25
著者
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市野 元信
Research Laboratories, Kohjin Co., Ltd.
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菊川 清見
Tokyo College of Pharmacy
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菊川 清見
Research Laboratory, Division of Fermentation and Chemical Products, Kohjin Co., Ltd.
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川田 いさ子
Research Laboratories, Kohjin Company, Ltd.
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市野 元信
Research Laboratories Kohjin Company Ltd.:(present Address)kitasato Biochemical Laboratories Bristol
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川田 いさ子
Research Laboratories Kohjin Company Ltd.
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