Collect. Czech. Chem. Commun. 1985, 50, 383-392

Synthesis of the sulfonamido derivatives of arabinonucleosides

Ladislav Novotný, Hubert Hřebabecký and Jiří Beránek

Institute of Organic Chemistry and Biochemistry, Czechoslovak Academy of Sciences, 166 10 Prague 6


Reaction of the sodium salt of 4-aminobenzenesulfonamide with cyclocytidine I and cyclouridine II led to the 2-sulfonamido derivatives V and VI while the reaction with the 5'-chloro derivatives of anhydronucleosides III and IV afforded compounds VIII and IX containing nitrogen bridge between the carbon atoms in position 2 and 5'. Kinetics of the model cyclization reaction of 5'-chloroarabinosylisocytosine (XI) was followed and the structure of prepared compounds was confirmed. Inhibition activity against L 1210 leukemia cells in the experiments in vitro was exhibited by compounds V (1.4 . 10-5 mol l-1) and VIII (3.3 . 10-6 mol l-1).