Synthetic Nucleosides and Nucleotides. 40. Selective Inhibition of Eukaryotic DNA Polymerase α by 9-(β-D-Arabinofuranosyl)-2-( p - n -butylanilino)adenine 5′-Triphosphate (BuAaraATP) and Its 2′-Up Azido Analog: Synthesis and Enzymatic Evaluations

Starting from 2',3',5'-tri-O-acetyl-2-iodoadenosine, 9-(beta-D-arabinofuranosyl)-2-(p-n-butylanilino)adenine and its 2'(S)-azido counterparts were synthesized in seven steps. These exhibited only moderate growth-inhibitory effects against mouse leukemic P388 cells (IC50 = 13-24 microM), although 5'-triphosphate derivatives showed strong and selective inhibitory action on calf thymus DNA polymerase alpha, but not on beta- and epsilon-polymerases from eukaryotes.