title: Synthesis of 3-O-methylviridicatin analogues with improved anti-TNF-alpha properties.
abstract: We synthesized 3-O-methylviridicatin and several analogues of this fungal metabolite. We showed that replacement of the methoxy moiety by a thiomethyl enhanced dramatically its ability to inhibit TNF-alpha secretion. These results strongly suggest that 4-phenyl-3-methylthioquinolinone may provide the basis for the development of new anti-inflammatory agents.
authors.affiliation: UMR 7175 LC1, ULP-CNRS, Faculté de Pharmacie, 67401 Illkirch, France.
authors.forename: Nigel
authors.initials: N
authors.lastname: Ribeiro
authors.forename: Helena
authors.initials: H
authors.lastname: Tabaka
authors.forename: Jean
authors.initials: J
authors.lastname: Peluso
authors.forename: Ludivine
authors.initials: L
authors.lastname: Fetzer
authors.forename: Can
authors.initials: C
authors.lastname: Nebigil
authors.forename: Serge
authors.initials: S
authors.lastname: Dumont
authors.forename: Christian D
authors.initials: CD
authors.lastname: Muller
authors.forename: Laurent
authors.initials: L
authors.lastname: Désaubry
mesh_terms: D002478:Cells, Cultured; D006801:Humans; D006912:Hydroxyquinolines / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D007962:Leukocytes / Q000187:drug effects / Q000378:metabolism; D015394:Molecular Structure; D015363:Quinolones / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D013329:Structure-Activity Relationship; D014409:Tumor Necrosis Factor-alpha / Q000037:antagonists & inhibitors* / Q000378:metabolism*
chemical_list: C116810:3-O-methylviridicatin; D006912:Hydroxyquinolines; D015363:Quinolones; D014409:Tumor Necrosis Factor-alpha