Glycosyl-oxycarbonylaminosulfonyl-2',3'-dideoxynucleoside derivatives as lipophilic nucleotide mimics. Synthesis and anti-HIV activity.
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.
Pérez-Pérez
M J
MJ
Instituto de Química Médica (C.S.I.C.), Madrid, Spain.
Balzarini
J
J
De Clercq
E
E
Camarasa
M J
MJ
D000998:Antiviral Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D002460:Cell Line; D015224:Dideoxynucleosides / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D004353:Drug Evaluation, Preclinical; D015497:HIV-1 / Q000187:drug effects* / Q000502:physiology; D006801:Humans; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D013329:Structure-Activity Relationship; D013936:Thymidine / Q000031:analogs & derivatives / Q000138:chemical synthesis / Q000494:pharmacology; D014779:Virus Replication / Q000187:drug effects
D000998:Antiviral Agents; D015224:Dideoxynucleosides; C059513:2',3'-dideoxyuridine; D013936:Thymidine