SYNTHESIS OF 3-[BENZYL(NAPHTHYLMETHYL)] DEIVATIVES OF 1-[5-(4-BROMO-PHENOXY)PENTYL]URACIL AS POTENTIAL INHOBITORS OF HUMAN CYTOMEGALOVIRUS REPRODUCTION
Synthesis of novel series of 1,3-disubstituted uracil derivatives as potential non-nucleoside inhibitors of human cytomegalovirus reproduction was carried out. Interaction of 1-bromo-5-(4-bromophenoxy)pentane with an equimolar amount of 2,4-bis(trimethylsilyloxy)pyrimidine in the absence of solvent at 160–170 °C during 1 hour leads to 1-[5-(4-bromophenoxy)pentyl]uracil in yield of 76 % after hydrolysis and preparative chromatography on silica gel. Its subsequent alkylation with benzyl chloride or bromide in anhydrous dimethylformamide in the presence of potassium carbonate at room temperature gives the corresponding 3-benzyl derivatives in yield of 78–91 %. The yield of target compounds was somewhat lower at 65-78 % when naphthyl-1(2)-methyl halide used as alkylating agents. The synthesized compounds are white crystalline substances, the chemical structure is confirmed by NMR spectroscopy. The physicochemical properties of new compounds are investigated.