Synthesis of 5-β-D-ribofuranosylnicotinamide and Its N-methyl derivative. The isosteric and isoelectronic analogues of nicotinamide nucleoside Journal Article
| Authors: | Kabat, M. M.; Pankiewicz, K. W.; Watanabe, K. A. |
| Article Title: | Synthesis of 5-β-D-ribofuranosylnicotinamide and Its N-methyl derivative. The isosteric and isoelectronic analogues of nicotinamide nucleoside |
| Abstract: | 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. © 1987, American Chemical Society. All rights reserved. |
| Keywords: | neoplasms; nad; ribonucleosides; niacinamide; priority journal; support, u.s. gov't, p.h.s. |
| Journal Title: | Journal of Medicinal Chemistry |
| Volume: | 30 |
| Issue: | 5 |
| ISSN: | 0022-2623 |
| Publisher: | American Chemical Society |
| Date Published: | 1987-05-01 |
| Start Page: | 924 |
| End Page: | 927 |
| Language: | English |
| DOI: | 10.1021/jm00388a030 |
| PUBMED: | 2952800 |
| PROVIDER: | scopus |
| DOI/URL: | |
| Notes: | Article -- Export Date: 5 February 2021 -- Source: Scopus |
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