The Novel Fluorinated C-6 Substituted Uracil Derivatives: Synthesis, Biological Evaluations, 1H And 13C NMR Conformational And X-Ray Crystal Structure Studies

Pyrimidine derivatives and their nucleosides have great biological significance because they exhibit a wide range of antiviral and anticancer activities. The pronounced biological activities exhibited by this class of compounds led us to synthesize the new type of C-6 alkylated pyrimidine derivatives and to evaluate their cytostatic and antiviral activities.1 Among all compounds evaluated, the compound containing a 2-hydroxy-3, 3, 3-trifluoro-1-propenyl side chain exhibited a pronounced effect against breast carcinoma (MCF-7), while the compound with a 2-fluoromethyl-2-acetoxypropyl chain exhibited moderate effect against cervical carcinoma (HeLa).2 A new series of the uracil derivatives with an acyclic side chain at the C-6 position was synthesized using lithiation of the 5, 6-dimethyl pyrimidine derivative and subsequent nucleophilic addition or substitution reactions of the organolithium intermediate thus obtained with fluorinated ketones and fluorinated esters. All synthesized compounds were evaluated for their cytostatic and antiviral activities.