Abstract
3(5)-Carboxamido-4-(β- d-ribofuranosyl)pyrazoles bearing 2′-benzamido ( 15 ) and 3′-mesyloxy ( 29 ) isosteric groups, as well as the tetrazole C-nucleosides with 2-benzamido-2-deoxy-β- d-ribofuranose ( 19 ) and 3-azido-3-deoxy-β- d-xylofuranose ( 36 ) as sugar segments, have been synthesized starting from d-glucose, by utilizing the 2,5-anhydro- d-glucose ethylene acetal derivatives 1 and 20 as divergent intermediates. The C-nucleosides 15 and 36 were shown to be moderate inhibitors of the in vitro growth of both N2a and BHK 21 tumour cell lines, whereas 29 showed a selective, although not potent cytotoxic activity against N2a cells. Compound 29 also showed a moderate in vitro antiviral activity towards the rabies virus.
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