3-(Adamantan-1-yl)-4-hydroxybenzyl Substituted Purines and Pyrimidines: Synthesis and Cytotoxic Activity

Selected adamantanyl purines and pyrimidines 1-10 were synthesized. These compounds were evaluated for cytotoxic activity against NCI-60 DTP human tumor cell line screen. N9-(3'-Adamantan-1-yl)-4'-hydroxy(benzyl)-2- amino-6-chloropurine, 3 and N9-[(3'-(Adamantan-1-yl)-4'-(2'',3'',4''-trifluorobenzyloxy)]benzyl-2-amino-6-chloropurine, 6 elicited significant cytotoxic activity with GI50 values in the 1–10 μM range for selected human tumor cell lines. While other compounds elicited moderate activity with GI50 values in the 10–20 μM range for most human tumor cell lines.