title: [Modification of pyrimidine nucleosides using nicotinic acid derivatives].
abstract: Interaction of nicotinoyl chloride in situ with 2'-deoxyuridine, its 3'-O-acetyl-, or 5'-O-trityl derivatives led to 3'-O-nicotinoyl-, 5'-O-nicotinoyl-, 3',5'-di-O-nicotinoyl-, and N3,3'-di-O-nicotinoyl-2'-deoxyuridine. Similarly, 5'-O-nicotinoyl-6-azauridine resulted from the reaction of 2',3'-O-ethoxymethylidene-6-azauridine followed by the deprotection. Reaction of 5'-amino-5'-deoxy-2',3'-O-ethoxymethylidene-6-azauridine with nicotinic acid in the presence of 2-ethoxy-1-ethoxycarbonyl-1,2-dihydroquinoline followed by the cleavage of the 2',3'-O-protecting group gave 5'-deoxy-5'-nicotinamido-6-azauridine. The same compound was obtained from 5'-amino-5'-deoxy-6-azauridine and N-succinimidyl nicotinate. Structures of the compounds obtained were corroborated by 1H NMR spectra. It is shown that 3',5'-di-O-nicotinoyl-2'- deoxyuridine and 5'-deoxy-5'-O-nicotinamido-6-azauridine are cytotoxic toward CaOv cells in vitro (CE50 10(-5) M).
authors.forename: S V
authors.initials: SV
authors.lastname: Makutova
authors.forename: I L
authors.initials: IL
authors.lastname: Plikhtiak
authors.forename: I V
authors.initials: IV
authors.lastname: Iartseva
authors.forename: T P
authors.initials: TP
authors.lastname: Ivanova
authors.forename: S Ia
authors.initials: SIa
authors.lastname: Mel'nik
mesh_terms: D000970:Antineoplastic Agents / Q000737:chemistry* / Q000494:pharmacology; D005260:Female; D006801:Humans; D009682:Magnetic Resonance Spectroscopy; D009525:Niacin / Q000031:analogs & derivatives* / Q000737:chemistry; D010051:Ovarian Neoplasms / Q000473:pathology; D011741:Pyrimidine Nucleosides / Q000737:chemistry* / Q000494:pharmacology; D014407:Tumor Cells, Cultured
chemical_list: D000970:Antineoplastic Agents; D011741:Pyrimidine Nucleosides; D009525:Niacin
vernacular_title: Modifikatsiia pirimidinovykh nukleozidov s ispol'zovaniem proizvodnykh nikotinovoĭ kisloty.