Novel synthetic route to the C-nucleoside, 2-deoxy benzamide riboside

Bioorg Med Chem Lett. 2012 Aug 15;22(16):5204-7. doi: 10.1016/j.bmcl.2012.06.069. Epub 2012 Jun 28.


2-Deoxy-C-nucleosides are a subcategory of C-nucleosides that has not been explored extensively, largely because the synthesis is less facile. Flexible synthetic procedures giving access to 2-deoxy-C-nucleosides are therefore of interest. To exemplify the versatility and highlight the limitations of a synthetic route recently developed to that effect, the first synthesis of 2-deoxy benzamide riboside is reported. Biological properties of this novel C-nucleoside are also discussed.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Benzamides / chemical synthesis*
  • Benzamides / chemistry
  • Benzamides / pharmacology
  • Cell Line, Tumor
  • Cell Proliferation / drug effects
  • Drug Screening Assays, Antitumor
  • HCT116 Cells
  • HT29 Cells
  • Humans
  • IMP Dehydrogenase / antagonists & inhibitors
  • IMP Dehydrogenase / metabolism
  • MCF-7 Cells
  • Nucleosides / chemical synthesis
  • Nucleosides / chemistry*
  • Nucleosides / pharmacology
  • Stereoisomerism


  • Benzamides
  • Nucleosides
  • IMP Dehydrogenase