title: Palladium-Catalyzed One-Pot Reaction of Hydrazones, Dihaloarenes, and Organoboron Reagents: Synthesis and Cytotoxic Activity of 1,1-Diarylethylene Derivatives.
abstract: A new three-component assembly reaction between N-tosylhydrazones, dihalogenated arenes, and boronic acids or boronate esters was developed, producing highly substituted 1,1-diarylethylenes in good yields. The two C-C bonds formed through this coupling have been catalyzed by a single Pd-catalyst in a one-pot fashion. It is noted that the one-pot pinacol boronate cross-coupling reaction generally provides products in high yields, offers an expansive substrate scope, and can address a broad range of aryl, styrene, vinyl, and heterocyclic olefinic targets. The scope of this one-pot coupling has been also extended to the synthesis of the 1,1-diarylethylene skeleton of the natural product ratanhine. The new compounds were evaluated for their cytotoxic activity, and this allowed the identification of compound 4ab that exhibits excellent antiproliferative activity in the nanomolar concentration range against HCT116 cancer cell lines.
authors.affiliation: †Université Paris-Sud, CNRS, BioCIS-UMR 8076, Equipe Labellisée Ligue Contre le Cancer, LabEx LERMIT, Laboratoire de Chimie Thérapeutique, Faculté de Pharmacie, rue J.-B. Clément, F-92296 Châtenay-Malabry, France.
authors.forename: Maxime
authors.initials: M
authors.lastname: Roche
authors.affiliation: †Université Paris-Sud, CNRS, BioCIS-UMR 8076, Equipe Labellisée Ligue Contre le Cancer, LabEx LERMIT, Laboratoire de Chimie Thérapeutique, Faculté de Pharmacie, rue J.-B. Clément, F-92296 Châtenay-Malabry, France.
authors.forename: Salim Mmadi
authors.initials: SM
authors.lastname: Salim
authors.affiliation: ‡Institut de Chimie des Substances Naturelles, UPR 2301, CNRS, avenue de la Terrasse, F-91198 Gif sur Yvette, France.
authors.forename: Jérôme
authors.initials: J
authors.lastname: Bignon
authors.affiliation: ‡Institut de Chimie des Substances Naturelles, UPR 2301, CNRS, avenue de la Terrasse, F-91198 Gif sur Yvette, France.
authors.forename: Hélène
authors.initials: H
authors.lastname: Levaique
authors.affiliation: †Université Paris-Sud, CNRS, BioCIS-UMR 8076, Equipe Labellisée Ligue Contre le Cancer, LabEx LERMIT, Laboratoire de Chimie Thérapeutique, Faculté de Pharmacie, rue J.-B. Clément, F-92296 Châtenay-Malabry, France.
authors.forename: Jean-Daniel
authors.initials: JD
authors.lastname: Brion
authors.affiliation: †Université Paris-Sud, CNRS, BioCIS-UMR 8076, Equipe Labellisée Ligue Contre le Cancer, LabEx LERMIT, Laboratoire de Chimie Thérapeutique, Faculté de Pharmacie, rue J.-B. Clément, F-92296 Châtenay-Malabry, France.
authors.forename: Mouad
authors.initials: M
authors.lastname: Alami
authors.affiliation: †Université Paris-Sud, CNRS, BioCIS-UMR 8076, Equipe Labellisée Ligue Contre le Cancer, LabEx LERMIT, Laboratoire de Chimie Thérapeutique, Faculté de Pharmacie, rue J.-B. Clément, F-92296 Châtenay-Malabry, France.
authors.forename: Abdallah
authors.initials: A
authors.lastname: Hamze
mesh_terms: D001896:Boron Compounds / Q000737:chemistry*; D002384:Catalysis; D002460:Cell Line; D003521:Cyclopropanes / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D005030:Ethylenes / Q000138:chemical synthesis* / Q000737:chemistry; D045325:HCT116 Cells / Q000737:chemistry / Q000187:drug effects; D006801:Humans; D006835:Hydrazones / Q000737:chemistry*; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry; D014753:Vinyl Compounds / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*
chemical_list: C000604892:5-(1-(3-(2-cyclopropylvinyl)-4-methoxyphenyl)vinyl)-1,2,3-trimethoxybenzene; D001896:Boron Compounds; D003521:Cyclopropanes; D005030:Ethylenes; D006835:Hydrazones; D014753:Vinyl Compounds; D010165:Palladium