与布累迪宁和吡唑呋林相关的某些1,2,3-三唑甲酰胺核苷的合成及生物活性

Synthesis and biological activity of certain 1,2,3-triazole carboxamide nucleosides related to bredinin and pyrazofurin.

作者信息

Revankar G R, Solan V C, Robins R K, Witkowski J T

出版信息

Nucleic Acids Symp Ser. 1981(9):65-8.

Abstract

5-Hydroxy-1-(beta-D-ribofuranosyl)-1,2,3-triazole-4-carboxamide (II) has been prepared by direct glycosylation of the trimethylsilyl derivative of 5-hydroxy-1,2,3-triazole-4-carboxamide (IV). The use of trimethylsilyltrifluoromethane sulfonate as a catalyst and 1-O-acetyl-2,3,5-tri-O-benzoyl-beta-D-ribofuranose in acetonitrile gave a 95% yield of a 1:1 mixture of V and VI as blocked nucleosides which were readily separated on a silica gel column. The synthesis of II was also achieved by the cycloaddition of 2,3,5-tri-O-benzoyl-beta-D-ribofuranosyl azide with ethyl malonamate. II shows significant antiviral activity against herpes and measles virus in vitro.

摘要

5-羟基-1-(β-D-呋喃核糖基)-1,2,3-三唑-4-甲酰胺（II）是通过5-羟基-1,2,3-三唑-4-甲酰胺（IV）的三甲基硅烷基衍生物的直接糖基化反应制备的。使用三甲基甲磺酸硅酯作为催化剂，在乙腈中用1-O-乙酰基-2,3,5-三-O-苯甲酰基-β-D-呋喃核糖，得到了95%产率的V和VI作为封闭核苷的1:1混合物，它们很容易在硅胶柱上分离。II的合成也通过2,3,5-三-O-苯甲酰基-β-D-呋喃核糖基叠氮化物与丙二酸乙酯的环加成反应实现。II在体外对疱疹病毒和麻疹病毒显示出显著的抗病毒活性。