A New Method of the Introduction of CF3‐ and C2F5‐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 (CnF2n+1)2Hg 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.
Novel peptide aldehydes (PAs) were identified as potent inhibitors of human cytomegalovirus (HCMV) in vitro. Although these compounds were highly effective against HCMV, they did not exhibit any activity against murine cytomegalovirus (MCMV). The purpose of this study was to test the antiviral activity of PA 8 as a representative of this novel class of inhibitors against HCMV in vivo. Because of the strict species specificity of HCMV we had to use two artificial animal models. In the first model, HCMV-infected human cells were entrapped into agarose plugs and transplanted into mice. In the second model, SCID mice were transplanted with human tissues that were subsequently infected with a clinical isolate of HCMV. In these two models the antiviral activity of PA 8 was clearly demonstrated, ganciclovir only being slightly superior in its in vivo antiviral activity.
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