Synthesis of 5-beta-D-ribofuranosylnicotinamide and its N-methyl derivative. The isosteric and isoelectronic analogues of nicotinamide nucleoside.
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.
D009243:NAD / Q000031:analogs & derivatives; D009369:Neoplasms / Q000188:drug therapy; D009536:Niacinamide / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000627:therapeutic use; D012263:Ribonucleosides / Q000138:chemical synthesis* / Q000627:therapeutic use
D012263:Ribonucleosides; D009243:NAD; C052349:5-ribofuranosylnicotinamide; C052350:5-ribofuranosyl-3-(aminocarbonyl)-1-methylpyridinium; D009536:Niacinamide