Synthesis and antiproliferative activity of 2′-O-allyl-1-β-D-arabinofuranosyl-uracil, -cytosine and -adenine

With the aim to design potential inhibitors of ribonucleotide reductase (RR), 2′-O-allyl-β-D-arabinofuranosyl-uracil (4), -cytosine (7) and -adenosine (10) were prepared and evaluated for their cytostatic activity against Molt4/C8, CEM and L1210 cell lines. Although our preliminary data do not allow to assess if RR is the intracellular target, the results point to differences in the (anti)metabolic behavior of these compounds. This study also offers a general synthesis of 2′-O-allyl-β-D-arabinofuranosyl nucleosides for potential applications in the preparation of 2′-O-allyl-β-D-oligoarabino nucleotides.