Eine neue Methods zur Einführung von CF₃‐ und C₂F₅‐Gruppen in Pyrimidinderivate und die Anti‐Herpes‐Aktivität der Verbindungen

Abstract

A New Method of the Introduction of CF 3 ‐ and C 2 F 5 ‐Groups into Pyrimidine Derivatives and their Antiherpes Activity A new method of the perfluoroalkylation of uracil derivatives is described. The irradiation of aqueous solutions of uracil and uracilnucleosides with bis‐(perfluoroalkyl) mercury (C n F 2n+1 ) 2 Hg n = 1, 2 under the exclusion of oxygen in the presence of catalytic amounts of azo‐bis‐isobutyronitril at 254 nm for several hours gave new 5‐perfluoroalkylated compounds. In this way we obtained 5‐trifluoromethyluracil ( 5a ), 5‐pentafluoroethyluracil ( 5b ), 5‐trifluoromethyl‐2′‐deoxyuridine ( 6a ), 5‐pentafluoroethyl‐2′‐deoxyuridine ( 6b ) and 1‐(ß‐D‐arabinofuranosyl)‐5‐trifluoromethyluracil ( 7a ) in different yields. The perfluoroalkylated compounds were tested against HSV‐1 and HSV‐2 viruses on human lungefibroblasts. The compounds are markedly less potent than other known nonfluorinated compounds.