[Modification of pyrimidine nucleosides using nicotinic acid derivatives].
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).
Makutova
S V
SV
Plikhtiak
I L
IL
Iartseva
I V
IV
Ivanova
T P
TP
Mel'nik
S Ia
SIa
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
D000970:Antineoplastic Agents; D011741:Pyrimidine Nucleosides; D009525:Niacin
Modifikatsiia pirimidinovykh nukleozidov s ispol'zovaniem proizvodnykh nikotinovoĭ kisloty.