TY - JOUR
T1 - Synthesis of 5-β-D-ribofuranosylnicotinamide and Its N-methyl Derivative. The Isosteric and Isoelectronic Analogues of Nicotinamide Nucleoside
AU - Kabat, Marek M.
AU - Pankiewicz, Krzysztof W.
AU - Watanabe, Kyoichi A.
PY - 1987/5/1
Y1 - 1987/5/1
N2 - The pyridine C-nucleosides 5-β-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 β anomer 1 was separated and treated with Mel to give 2.
AB - The pyridine C-nucleosides 5-β-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 β anomer 1 was separated and treated with Mel to give 2.
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U2 - 10.1021/jm00388a030
DO - 10.1021/jm00388a030
M3 - Article
C2 - 2952800
AN - SCOPUS:0023233776
SN - 0022-2623
VL - 30
SP - 924
EP - 927
JO - Journal of Medicinal Chemistry
JF - Journal of Medicinal Chemistry
IS - 5
ER -