Synthesis and cytotoxic activity of C-glycosidic nicotinamide riboside analogues.
The C-glycosidic nicotinamide riboside analogue (2) was prepared by reaction of ribonolactone 24 with the lithiated oxazoline 19 followed by triethylsilane reduction to 26 and deprotection. Selective phosphorylation to the pseudonucleotide 34 was effected via the isopropylidene compound 33. In contrast to the benzoic acid riboside (28) the benzamide riboside (2) showed extremely high cytotoxicity at nanomolar concentrations to S49.1 lymphoma cells but only slightly increased dexamethasone toxicity.
Krohn
K
K
Fachbereich Chemie und Chemietechnik, Universität-GH Paderborn, Germany.
Heins
H
H
Wielckens
K
K
D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D001549:Benzamides / Q000138:chemical synthesis* / Q000494:pharmacology; D001565:Benzoates / Q000138:chemical synthesis / Q000494:pharmacology; D019817:Benzoic Acid; D008223:Lymphoma / Q000473:pathology; D009243:NAD / Q000031:analogs & derivatives* / Q000378:metabolism / Q000494:pharmacology; D000067856:Poly(ADP-ribose) Polymerase Inhibitors; D014407:Tumor Cells, Cultured / Q000187:drug effects
D000970:Antineoplastic Agents; D001549:Benzamides; D001565:Benzoates; D000067856:Poly(ADP-ribose) Polymerase Inhibitors; D009243:NAD; D019817:Benzoic Acid