Synthesis and Biological Evaluation of Some D-Xylofuranosyl-Pyridine C-Nudeosides

Abstract

The addition reaction of either 3-bromo-5-lithiopyridine (2a) or 3-cyano-5-lithiopyridine (2b) to 2,4:3,5-di-O-benzylidene-aldehydo-D-xylose (1) gave a D-gulo/D-ido mixture of respectively 3-bromo- and 3-cyano-5-(2,4;3,5-di-O-benzylidene-pentitol-1-yl)pyridine (3a, b). Mesylation of C-1′ followed by reaction with CF₃COOH/H₂O resulted in the formation of the corresponding D-xylo-furanosyl pyridine C-nucleosides. 3-Cyano-5-D-xylofuranosylpyridine (5b) was converted to 3-carbamoyl-5-D-xylofuranosylpyridine (6) with Amberlite IRA 400 (OH⁻). The D-xylofuranosyl C-nucleosides were evaluated for their antiviral and cytostatic activity. No significant activity was found.