Bioorganic & Medicinal Chemistry 1993-10-01

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

M J Pérez-Pérez, J Balzarini, E De Clercq, M J Camarasa

Index: Bioorg. Med. Chem. 1(4) , 279-84, (1993)

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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.