Synthesis and evaluation of in vitro anticancer activity of some novel isopentenyladenosine derivatives.

The present study describes the synthesis, the characterization and the evaluation of some derivatives of N(6)-isopentenyladenosine on T24 human bladder carcinoma cells. In particular we have modified the hydroxyl groups in the ribose moiety, the position of the isopentenyl chain in the purine ring and the base moiety. The structures of the compounds were confirmed by standard studies of NMR, MS and elemental analysis. We here show that only two derivatives, 1-(3-methyl-2-butenylamino)-9-(3'-deoxy-beta-d-ribofuranosyl)-purine hydrobromide and 2-amino-6-(3-methyl-2- butenylamino)-9-(beta-d-ribofuranosyl)-purine, inhibit the growth of T24 cells, although to a lower extent than N(6)-isopentenyladenosine. We conclude that the integrity of ribosidic and purine moiety and the N(6) position of the chain are essential for maintaining the antiproliferative activity. Copyright 2010 Elsevier Ltd. All rights reserved.