Synthesis of 5-beta-D-ribofuranosylnicotinamide and its N-methyl derivative. The isosteric and isoelectronic analogues of nicotinamide nucleoside

J Med Chem. 1987 May;30(5):924-7. doi: 10.1021/jm00388a030.

Abstract

The pyridine C-nucleosides 5-beta-D-ribofuranosylnicotinamide and its N-methylpyridinium derivative (1 and 2), which are isosteric and isoelectronic, respectively, to nicotinamide nucleoside were synthesized. Condensation of 3-bromo-5-lithiopyridine with 2,4:3,5-di-O-benzylidene-D-aldehydoribose (7) afforded an allo/altro mixture of the corresponding bromopyridine derivatives, which were converted into nicotinamide C-nucleoside precursors 10. Mesylation of the hydroxyl group of 10 followed by acid hydrolysis of the product afforded the anomeric nicotinamide C-nucleosides. The beta anomer 1 was separated and treated with MeI to give 2.

Publication types

  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • NAD / analogs & derivatives
  • Neoplasms / drug therapy
  • Niacinamide / analogs & derivatives*
  • Niacinamide / chemical synthesis
  • Niacinamide / therapeutic use
  • Ribonucleosides / chemical synthesis*
  • Ribonucleosides / therapeutic use

Substances

  • Ribonucleosides
  • NAD
  • 5-ribofuranosylnicotinamide
  • 5-ribofuranosyl-3-(aminocarbonyl)-1-methylpyridinium
  • Niacinamide