[Synthesis and cytotoxic properties of anomeric 5-substituted 3'-azido-2',3'-dideoxyuridines].

Autor: Bakhmedova AA, Iartseva IV, Zhukova OS, Volosiuk TP, Iurkevich AM, Mel'nik SIa
Jazyk: ruština
Zdroj: Bioorganicheskaia khimiia [Bioorg Khim] 1992 Mar; Vol. 18 (3), pp. 444-8.
Abstrakt: 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%.
Databáze: MEDLINE