Preparation of 1-(3-C-(propa-1,2-dienyl)-D-ribo-pentofuranosyl)uracil, an allenic nucleoside.
The Crabbé reaction was extended to the preparation of C-3'-allenyl-uridine. The effects of solvent and protecting group on the reaction were studied. The conversion in refluxing dioxan of disilyl either 3 proceeds to the corresponding allenic nucleoside 7; whereas, in refluxing THF the Mannich base 5 was obtained. Fully deprotected Mannich base and allenic uridines 6 and 9 were tested for their antitumor activity.
Dauvergne
J
J
Laboratoire de Chimie Organique Biologique Associé au CNRS, Faculté de Chimie, Université Louis Pasteur, Strasbourg, France.
Burger
A
A
Biellmann
J F
JF
D000483:Alleles; D000818:Animals; D000970:Antineoplastic Agents / Q000494:pharmacology; D020128:Inhibitory Concentration 50; D051379:Mice; D008956:Models, Chemical; D014407:Tumor Cells, Cultured; D014466:Ultraviolet Rays; D014498:Uracil / Q000031:analogs & derivatives*; D014529:Uridine / Q000031:analogs & derivatives* / Q000494:pharmacology*
C453720:1-(3-C-(propa-1,2-dienyl)pentofuranosyl)uracil; D000970:Antineoplastic Agents; D014498:Uracil; D014529:Uridine