SYNTHESIS AND BIOLOGIC ACTIVITY OF PURINE 2'-DEOXY-2'-FLUORO-RIBONUCLEOSIDES

The synthesis of 3,5-di-O-benzoyl-2-deoxy-2-fluoro-D-ribofuranosyl bro mide (8) and its reaction with 2,6-dichloropurine by fusion and with m ercuric cyanide catalysis is described. The resulting nzoyl-2-deoxy-2- fluoro-beta-D-ribofuranosyl)purine (13) was converted to the 2-fluoroa denine (16), the 2-chloroadenine (17), 2,6-diaminopurine (12), and gua nine (14) nucleosides by standard procedures. These nucleosides were c ytotoxic to a number of cell lines in culture. The 2-haloadenine nucle osides 16 and 17 gave modest increases in lifespan when tested against the P388 leukemia in mice.