Glycosyl-oxycarbonylaminosulfonyl-2',3'-dideoxynucleoside derivatives as lipophilic nucleotide mimics. Synthesis and anti-HIV activity

Abstract

Several lipophilic-2',3'-dideoxynucleotide analogues have been synthesized and tested against Human Immunodeficiency Virus (HIV). Glycosyl-oxycarbonylaminosulfonyl-analogues of 3'-deoxythymidine and 2',3'-dideoxyuridine have been synthesized by reaction of 2,3,4,6-tetra-O-benzoyl-alpha-D-glucopyranose with chlorosulfonyl isocyanate and the corresponding 2',3'-dideoxynucleoside. Another series of 5'-phosphate-like-3'-deoxythymidine nucleosides (5'-O-alkyl-sulfamoyl- and 5'-O-carbamoyl-3'-deoxythymidine) have also been prepared. Both series of compounds can be considered as lipophilic nucleotide mimics.