title: Tandem one-pot palladium-catalyzed coupling of hydrazones, haloindoles, and amines: synthesis of amino-N-vinylindoles and their effect on human colon carcinoma cells.
abstract: The synthesis of amino-substituted N-vinylazoles was achieved by a new palladium-assisted tandem catalytic reaction involving N-tosylhydrazones, halo-substituted azoles, and amines. Accordingly, two Csp(2)-N bonds were formed through two mechanistically distinct reactions using a single Pd(II)/Pd(0) catalyst system in a one-pot fashion. This work paves the way for the design of biological relevant compounds in an amino-substituted N-vinylindole series. Among several polyoxygenated derivatives evaluated, compounds 5e and 5u were found to exhibit good antiproliferative activity.
authors.affiliation: Laboratoire de Chimie Thérapeutique, Equipe Labellisée Ligue Contre le Cancer, LabEx LERMIT, Faculté de Pharmacie, Université Paris-Sud , CNRS, BioCIS-UMR 8076, 5 rue J.-B. Clément, Châtenay-Malabry, F-92296 Paris, France.
authors.forename: Maxime
authors.initials: M
authors.lastname: Roche
authors.forename: Jérôme
authors.initials: J
authors.lastname: Bignon
authors.forename: Jean-Daniel
authors.initials: JD
authors.lastname: Brion
authors.forename: Abdallah
authors.initials: A
authors.lastname: Hamze
authors.forename: Mouad
authors.initials: M
authors.lastname: Alami
mesh_terms: D000588:Amines / Q000737:chemistry*; D002384:Catalysis; D045744:Cell Line, Tumor; D049109:Cell Proliferation / Q000187:drug effects*; D003110:Colonic Neoplasms; D006801:Humans; D006835:Hydrazones / Q000737:chemistry*; D007211:Indoles / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry*; D014105:Tosyl Compounds / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D014753:Vinyl Compounds / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*
chemical_list: C000595116:1-(1-(3,4,5-trimethoxyphenyl)vinyl)-1H-indol-4-amine; C000595115:5-(indolin-1-yl)-1-(1-(3,4,5-trimethoxyphenyl)vinyl)-1H-indole; D000588:Amines; D006835:Hydrazones; D007211:Indoles; D014105:Tosyl Compounds; D014753:Vinyl Compounds; D010165:Palladium