Synthesis ofN-1-Alkylated 6-Benzyluracil-5-carboxylic Esters as Potential Non-Nucleoside Reverse Transcriptase Inhibitors

A series of N-1-alkylated 6-benzyluracil-5-carboxylic esters 4a-h were synthesized by reacting imines of 3-oxo-4-phenylbutyrates with N-(chlorocarbonyl) isocyanate. An N-1-(4-methoxybenzyl) group could be removed in a dealkylation reaction to give the ethyl and allyl esters 5a and 5b, respectively. They were N-1-alkylated with chloromethyl ethyl ether or dialloxymethane. Unfortunately no biological activity against HIV-1 and HSV was observed for any of the synthesized compounds.