Synthesis and antiinflammatory activity of 6-oxo-1-(beta-D-ribofuranosyl)nocotinic acid and related derivatives.
5-Substituted 1-(beta-D-ribofuranosyl)pyridine-2-ones (6-oxonicotinic acid nucleosides) were prepared by direct glycosylation of 5-ntrio-, 5-carbomethoxy-, 5-carboxamido-, 5-amino, 5-carbobenzyloxyamino-, and 5-acetamido-2-trimethylsilyloxy or corresponding 2-methoxypyridine derivatives by the Hilbert-Johnson method. The glycosylation products were deblocked by conventional procedures and substituents at the 5 position were modified to give the 5-carboxamide, carboxyhydrazide, and carboxylic acid. Only 1-(beta-D-ribofuranosyl)pyridin-2-one-5-carboxylic acid [1-(beta-D-ribofuranosyl)-6-oxonicotinic acid (12), showed significant activity in treating adjuvant-induced arthritis in rats.
D000818:Animals; D000893:Anti-Inflammatory Agents / Q000138:chemical synthesis*; D001169:Arthritis, Experimental / Q000503:physiopathology; D008722:Methods; D009539:Nicotinic Acids / Q000138:chemical synthesis / Q000494:pharmacology; D051381:Rats; D012263:Ribonucleosides / Q000138:chemical synthesis* / Q000494:pharmacology
D000893:Anti-Inflammatory Agents; D009539:Nicotinic Acids; D012263:Ribonucleosides