Studies on Compounds Related to Antitumor Agents. Syntheses of 8-Substituted N⁶, N⁶-Dimethyladenosine Derivatives

Abstract

N⁶, N⁶-Dimethyl-8-methylsulfonyladenosine, obtained from N⁶, N⁶-dimethyl-8-methylthioadenosine by highly selective oxidation with KMnO₄, was treated with cyanide ion to give 8-cyano-N⁶, N⁶-dimethyladenosine. The conversion of the cyano group to methyl imidate, methoxycarbonyl, carbamoyl, carbothioamide, and carboxylic acid moieties was achieved. These 8-substituted N⁶, N⁶-dimethyladenosines may possess resonances structures involving positions 6 and 8 in adenosine, as indicated by the spectroscopic data. They showed no antitumor activity.