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Nucleosides, 38 1) The Ribonucleosides of Allopurinol
Author(s) -
Lichtenthaler Frieder W.,
Cuny Eckehard
Publication year - 1981
Publication title -
chemische berichte
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 0009-2940
DOI - 10.1002/cber.19811140505
Subject(s) - chemistry , allopurinol , trifluoromethanesulfonate , trimethylsilyl , xanthine oxidase , stereochemistry , catalysis , trimethylsilyl trifluoromethanesulfonate , medicinal chemistry , glycosylation , organic chemistry , enzyme , biochemistry , medicine , pathology
Of the various conceivable ribonucleosides of allopurinol, the N ‐1‐, N ‐2‐, and N ‐5‐isomers (9c‐11c) as well as the 1, 5‐and 2,5‐bis‐ribosylated derivatives 6c and 7c have been prepared via stannic chloride‐induced glycosylation of bis (trimethylsilyl)allopurinol 4 with acylated ribofuranoses (5) . Trimethylsilyl triflate as catalyst in addition produced the O 4 ‐ribosylated isomer 8a . – The structures of the products were secured from UV, 1 H, and 13 C NMR data. –Their xanthine oxidase inhibitory activity was evaluated.