[Synthesis and cytotoxic properties of anomeric 5-substituted 3'-azido-2',3'-dideoxyuridines].
Glycosylation of trimethylsilyl derivatives of 5-benzyloxymethyl- and 5-hydroxymethyluracil with 3-azido-2,3-dideoxy-5-O-benzoyl-D-ribofuranosyl chloride (prepared from ethyl 3-azido-2,3-dideoxy-5-O-benzoyl-D-ribofuranoside) and subsequent deacylation gave in both cases a mixture of anomeric 3'-azido-2',3'-dideoxy-5-benzyloxymethyl-or 5-hydroxymethyluridines. The anomers were separated by preparative TLC and their structures were studied by UV, IR and 1H-NMR spectroscopy. It is shown that 1-(3-azido-2,3-dideoxy-alpha-D-ribofuranosyl)-5-benzyloxymethyluracil has cytotoxic activity in vitro: in 10(-5)-10(-4) M concentrations it inhibits the thymidine incorporation into DNA of CaOv cells on 78.6-95.2%.
Bakhmedova
A A
AA
Iartseva
I V
IV
Zhukova
O S
OS
Volosiuk
T P
TP
Iurkevich
A M
AM
Mel'nik
S Ia
SIa
D000998:Antiviral Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D002460:Cell Line; D002470:Cell Survival / Q000187:drug effects*; D002855:Chromatography, Thin Layer; D004247:DNA / Q000378:metabolism; D006031:Glycosylation; D009682:Magnetic Resonance Spectroscopy; D013055:Spectrophotometry, Infrared; D013056:Spectrophotometry, Ultraviolet; D013936:Thymidine / Q000378:metabolism; D015215:Zidovudine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000494:pharmacology
D000998:Antiviral Agents; D015215:Zidovudine; D004247:DNA; C058803:3'-azido-2',3'-dideoxyuridine; D013936:Thymidine
Sintez i tsitotoksicheskie svoĭstva anomernykh 5-zameshchennykh 3'-azido-2',3'-didezoksiuridinov.