Paper
Synthesis and biological activity of certain 1,2,3-triazole carboxamide nucleosides related to bredinin and pyrazofurin.
Published 1981 · Revankar Gr, Solan Vc, Robins Rk
Nucleic Acids Symposium Series
1
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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.
5-Hydroxy-1-(beta-D-ribofuranosyl)-1,2,3-triazole-4-carboxamide (II) shows significant antiviral activity against herpes and measles virus in vitro.
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