title: An efficient coupling of N-tosylhydrazones with 2-halopyridines: synthesis of 2-α-styrylpyridines endowed with antitumor activity.
abstract: The synthesis of 2-α-styrylpyridines has been carried out by using the coupling of polyoxygenated N-tosylhydrazones with various 2-halopyridines. We demonstrated that the use of a catalytic amount of PdCl2(MeCN)2 in combination with a bidentate ferrocene DPPF or a monodentate alkyl phosphine (t)Bu2MeP-HBF4 constitutes an efficient protocol for this coupling, providing 2-α-styrylpyridines 2 in satisfactory to good yields. Among several polyoxygenated derivatives 2 evaluated, compound 2aa was found to exhibit excellent antiproliferative and antimitotic activities comparable to that of the reference compound isoCA-4.
authors.affiliation: Université Paris-Sud, CNRS, BioCIS UMR 8076, LabEx LERMIT, Laboratoire de Chimie Thérapeutique, Faculté de Pharmacie, 5 rue J-B Clément, Châtenay-Malabry, F-92296, France.
authors.forename: Marie
authors.initials: M
authors.lastname: Lawson
authors.forename: Abdallah
authors.initials: A
authors.lastname: Hamze
authors.forename: Jean-François
authors.initials: JF
authors.lastname: Peyrat
authors.forename: Jérôme
authors.initials: J
authors.lastname: Bignon
authors.forename: Joelle
authors.initials: J
authors.lastname: Dubois
authors.forename: Jean-Daniel
authors.initials: JD
authors.lastname: Brion
authors.forename: Mouad
authors.initials: M
authors.lastname: Alami
mesh_terms: D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D002384:Catalysis; D045744:Cell Line, Tumor; D049109:Cell Proliferation / Q000187:drug effects; D003106:Colon / Q000187:drug effects; D003110:Colonic Neoplasms / Q000188:drug therapy; D054879:Halogenation; D006801:Humans; D006835:Hydrazones / Q000138:chemical synthesis / Q000737:chemistry*; D010165:Palladium / Q000737:chemistry; D011725:Pyridines / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D013343:Styrenes / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*
chemical_list: D000970:Antineoplastic Agents; D006835:Hydrazones; D011725:Pyridines; D013343:Styrenes; C003347:4-stilbazole; D010165:Palladium; C008756:palladium chloride