N 6 -substituted adenosines. Cytokinin and antitumor activities

A series of N 6 -adenosine derivatives were synthesized by alkylation of N 6 -acetyl-2′,3′,5′-tri- O -acetyladenosine ( 1 ) with alkyl halides and alcohols. It was shown that propargyl derivative 2a is a good substrate for copper(I) catalyzed Huisgen [3+2] cycloaddition with azides. This click-reaction can be used for preparation of the libraries of 1,2,3-triazolyl modified adenosines. Biological activities of N 6 -adenosines were studied in two plant and six human cancer cell assays. The remarkable parallel between cytokinin and cytotoxic activities was found. The most cytokinin active compounds 3c – 3e at the same time appeared to be the most potent cytotoxic agents.