Synthesis of Mimics to 5-(2″-thienyl)-2′,3′-β-Dideoxyuridine Triphosphate

Abstract

A series of S'-amido derivatives of S-(2".thienyl)-2',3',S'-13-trideoxyuridine were prepared. The cornpounds were tested for their inhibition of cellular DNA polymerase a. and HIV-RT. The succinic fumaric and maleic acid derivatives of S-(2"-thienyl)-2',3',S'-13-trideoxyuridine were investigated. None of the compounds inhibited HIV-RT. The fumaric acid derivative inhibited DNA pol a. with ICec 33 J.!g mr',The succinic acid derivative was about half as active with ICso 76 J.!g mr", The S'-N-acyl derivatives also were structurally compared to the monomethyl ester of the triphosphate using the Sybyl program.