Improved synthesis of beta-D-6-methylpurine riboside and antitumor effects of the beta-D- and alpha-D-anomers.

Canio J Marasco, Paula J Pera, Arthur J Spiess, Ralph Bernacki, Janice R Sufrin

Index: Molecules 10(8) , 1015-20, (2005)

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Abstract

6-Methylpurine-beta-D-riboside (beta-D-MPR) has been synthesized by coupling 6-methylpurine and 1-O-acetyl-2,3,5-tri-O-benzoyl-D-ribose using conditions that produce the beta-D-anomer exclusively. The in vitro antitumor effects of beta-D-MPR and 6-methyl-purine-alpha-D-riboside (alpha-D-MPR) in five human tumor cell lines showed that beta-D-MPR was highly active (IC(50) values ranging from 6 to 34 nM). alpha-D-MPR, although less active than beta-D-MPR, also exhibited significant antitumor effects (IC50 values ranging from 1.47 to 4.83 microM).