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The synthesis and anticancer evaluation of new series of nucleosides constructed on 5/6-azidoglycosyl or glucuronamide moieties and containing an  O - or an  N -dodecyl chain, respectively, are disclosed. Based on our previous results, their structures were planned to preclude them to act  via  a similar metabolic pathway than that of clinically used nucleoside antimetabolites, against which cancer cells frequently acquire resistance.  Xylo  and  gluco -configured 5/6-azido-1,2-di- O -acetyl furanosyl and pyranosyl donors containing a 3- O -dodecyl group were synthesized from diacetone- d -glucose and were subsequently coupled with silylated uracil or 2-acetamido-6-chloropurine.  N -Dodecyl glucuronamide-based nucleosides were accessed from acetonide-protected glucofuranurono-6,3-lactone, which was converted in few steps into  O -benzylated 1,2-di- O -acetyl furanuronamide or pyranuronamide derivatives to undergo further  N -glycosylation. Both types of nucleosides demonstrated notorious antiproliferative effects in chronic myeloid leukemia (K562) and in breast cancer (MCF-7) cells. The most potent molecules were a 6ʹ-azidoglucopyranosyl N 7 -linked purine nucleoside and glucofuranuronamide derivatives comprising N 1 -linked uracil and N 7 -linked purine units with activities in the single-digit micromolar order of concentration against both cell lines. Their GI 50  values in MCF-7 cells were similar or  ca.  3-fold lower than that of the standard drug 5-fluorouracil. Cell cycle studies and immunoblotting analysis of apoptosis-associated proteins in treated K562 cells indicated that the antiproliferative effect of the most effective nucleosides is based on apoptosis induction.

Novel dodecyl-containing azido and glucuronamide-based nucleosides exhibiting anticancer potential