Synthese und biochemische Aktivität perfluoralkylierter Derivate des 5′‐Desoxy‐5′‐fluor und 2′,5′‐Didesoxy‐5′‐fluor‐uridins

Synthesis and Biochemical Activity of Perfluoroalkylated Derivatives of 5′-Deoxy-5′-fluoro-, and 2′, 5′-Dideoxy-5′-fluorouridine 5-Perfluoroalkylated 5′-deoxy-5′-fluoro-, and 2′,5′-dideoxy-5′-fluorouridine are obtained by the reaction of 5′-fluorouridine or 2′,5′-dideoxy-5′-fluorouridine, respectively, with a perfluoroalkyl-coppercomplex in DMSO under inert conditions, and at temperatures of about 100 °C. Analogously 5-perfluoroethyl, 5-perfluorobutyl, and 5-perfluorohexyl derivatives of uridine, and 5-perfluoroethyl, and 5-perfluorobutyl derivatives of 2′-deoxyuridine could be isolated. It is shown either by mass spectroscopy or by 1H-n.m.r. spectroscopy that the substitution always takes place at the 5-position of the pyrimidine. The 5-perfluoroethyl derivatives are particularly effective as cytostatics.