Novel L-lyxo and 5'-deoxy-5'-modified TSAO-T analogs: synthesis and anti-HIV-1 activity.
Novel L-lyxo-TSAO-T analogs with an inverted configuration at the C-4'-position of the sugar moiety and 5'-deoxy-5'-modified TSAO-T derivatives have been prepared and evaluated for their inhibitory effect on human immunodeficiency virus type 1 (HIV-1) and type 2 (HIV-2) replication in cell culture. None of the compounds showed marked antiviral efficacy. The inactivity of the TSAO-T derivatives may most likely be explained by either their different 4'-configuration or their different chemical structure that may not allow an optimal interaction of the molecules with the lipophilic binding pocket of the HIV-1 reverse transcriptase.
Ingate
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Instituto de Química Médica (C.S.I.C.), Madrid, Spain.
De Clercq
E
E
Balzarini
J
J
Camarasa
M J
MJ
D019380:Anti-HIV Agents / Q000737:chemistry / Q000494:pharmacology*; D002461:Cell Line, Transformed; D015497:HIV-1 / Q000187:drug effects*; D015498:HIV-2 / Q000187:drug effects; D006801:Humans; D015394:Molecular Structure; D013141:Spiro Compounds / Q000737:chemistry / Q000494:pharmacology*; D013936:Thymidine / Q000031:analogs & derivatives* / Q000737:chemistry / Q000494:pharmacology; D014407:Tumor Cells, Cultured; D014529:Uridine / Q000031:analogs & derivatives
D019380:Anti-HIV Agents; D013141:Spiro Compounds; D013936:Thymidine; C075132:TSAO-T; D014529:Uridine