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

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• 作者：Roberta Ottria ; Silvana Casati ; Ada Manzocchi ; Erika Baldoli ; Massimo Mariotti ; Jeanette A.M. Maier ; Pierangela Ciuffreda
• 关键词：Isopentenyladenosine ; Modified nucleosides ; Antitumor agents ; Bladder carcinoma cells
• 刊名：Bioorganic and Medicinal Chemistry
• 出版年：2010
• 出版时间：15 June 2010
• 年：2010
• 卷：18
• 期：12
• 页码：4249-4254
• 全文大小：494 K

文摘

The present study describes the synthesis, the characterization and the evaluation of some derivatives of N⁶-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-β-d-ribofuranosyl)-purine hydrobromide and 2-amino-6-(3-methyl-2- butenylamino)-9-(β-d-ribofuranosyl)-purine, inhibit the growth of T24 cells, although to a lower extent than N⁶-isopentenyladenosine. We conclude that the integrity of ribosidic and purine moiety and the N⁶ position of the chain are essential for maintaining the antiproliferative activity.