Synthesis and anti-HIV activity of alpha-thiophenoxy-hydroxyethylamide derivatives.
A series of new anti-HIV derivatives containing a novel alpha-thiophenoxyhydroxyethylamide core have been synthesized, using S-phenylbenzenethiosulfonate as the thiosulfenylating reagent. Some of the new synthesized compounds (1a, 1c, 1g, 1i, 1j and 1l) inhibited HIV replication in cell culture assays (syncytia formation) with effective concentrations (EC(50)) ranging from 0.1-1 microM. Incorporation of thiophenoxy substitution within various pseudomimetic peptide backbones provided a series of highly potent HIV inhibitors.
Laboratoire de Chimie Biomoléculaire, Faculté des Sciences de Luminy, Case 901, 163 avenue de Luminy, 13288 cedex 9, Marseille, France.
M
M
Medou
G
G
Priem
L
L
Rocheblave
G
G
Pepe
M
M
Meyer
J C
JC
Chermann
J L
JL
Kraus
D000473:Alkanes / Q000138:chemical synthesis / Q000494:pharmacology; D000577:Amides / Q000138:chemical synthesis / Q000494:pharmacology; D019380:Anti-HIV Agents / Q000138:chemical synthesis* / Q000494:pharmacology*; D002460:Cell Line; D004353:Drug Evaluation, Preclinical; D017320:HIV Protease Inhibitors / Q000138:chemical synthesis / Q000494:pharmacology; D006801:Humans; D009682:Magnetic Resonance Spectroscopy; D013329:Structure-Activity Relationship; D014407:Tumor Cells, Cultured; D014779:Virus Replication / Q000187:drug effects
D000473:Alkanes; D000577:Amides; D019380:Anti-HIV Agents; D017320:HIV Protease Inhibitors