Synthesis of 5-Benzyl and 5-Benzyloxybenzyl 2,2′-Anhydrouridines and Related Nucleoside Analogs as Inhibitors of Uridine Phosphorylase

Furanosyl analogs of BAU (5-benzylacyclouridine) and BBAU (5-benzyloxybenzylacyclouridine), two potent inhibitors of uridine phosphorylase, were synthesized and evaluated as potential cancer chemotherapeutic agents. The analogs included ribosides, 2,2′-anhydro nucleosides, arabinosides and deoxyribosides. The anhydrouridine intermediates were potent inhibitors of uridine phosphorylase and good potentiators of FdUrd activity in human tumor cells in culture.