Use of 1,3-dioxolanes in the syntheses of alpha-branched alkyl and aryl N-9-[2-(phosphonomethoxy)ethyl]purines

Abstract

Syntheses of various alkyl and aryl substituted N-9-[2-(phoshonomethoxy)ethyl]purines from a number of 2-alkyl(aryl)-1,3-dioxolanes were developed in preparative yields. The cleavage of a dioxolane ring with Lewis acids was chosen for preparation of suitable phosphonate building blocks as a key reaction step followed by their Mitsunobu reaction with purine bases. Obtained phosphonate derivatives were tested as potential HG(X)PRTase inhibitors. In contrast to previously published N-9-[2-(phosphonoethoxy)ethyl]purines, no inhibitory activity towards this enzyme was observed