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腺苷型核苷的N-氧化物会发生嘧啶环的开环和闭环，生成5-氨基-4-(1,2,4-恶二唑-3-基)咪唑衍生物。

N-oxides of adenosine-type nucleosides undergo pyrimidine ring opening and closure to give 5-amino-4-(1,2,4-oxadiazol-3-yl)imidazole derivatives.

作者信息

Nowak Ireneusz, Cannon John F, Robins Morris J

机构信息

Department of Chemistry and Biochemistry, Brigham Young University, Provo, Utah 84602-5700, USA.

出版信息

Org Lett. 2006 Sep 28;8(20):4565-8. doi: 10.1021/ol061715v.

DOI:10.1021/ol061715v
PMID:16986951
Abstract

Treatment of acylated adenosine N-oxides with carboxylic anhydrides and thiophenol resulted in pyrimidine ring opening followed by exocyclic ring closure. Ammonolysis gave 5-amino-4-(5-substituted-1,2,4-oxadiazol-3-yl)-1-(beta-d-ribofuranosyl)imidazole derivatives, whereas iodine in methanol selectively unmasked the 5-amino group. Related flexible nucleoside analogues can be prepared from adenine-type precursors.

摘要

用羧酸酐和苯硫酚处理酰化腺苷N-氧化物会导致嘧啶环开环，随后发生环外闭环。氨解得到5-氨基-4-(5-取代-1,2,4-恶二唑-3-基)-1-(β-D-呋喃核糖基)咪唑衍生物，而甲醇中的碘选择性地使5-氨基暴露。相关的柔性核苷类似物可由腺嘌呤型前体制备。

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