title: Palladium-catalyzed direct addition of arylboronic acids to 2-aminobenzonitrile derivatives: synthesis, biological evaluation and in silico analysis of 2-aminobenzophenones, 7-benzoyl-2-oxoindolines, and 7-benzoylindoles.
abstract: A palladium-catalyzed direct addition of arylboronic acids to unprotected 2-aminobenzonitriles has been developed, leading to a wide range of 2-aminobenzophenones with moderate to excellent yields. The transformation has broad scope and high functional group tolerance. Moreover, 2-oxoindoline-7-carbonitrile and indole-7-carbonitrile were applicable to this process for the construction of 7-benzoyl-2-oxoindolines and 7-benzoylindoles, respectively. Among the compounds examined, compound 4e possessed the most potent anticancer activity against H446 and HGC-27 in vitro, with IC50 values of 0.02 μmol L(-1) and 0.09 μmol L(-1), respectively, while compound 4a showed the best potent anticancer activity against SGC-7901 with an IC50 value of 0.01 μmol L(-1). Furthermore, we also performed in silico molecular docking calculations to investigate the interaction mode and binding affinity between the examined compounds and their tubulin target.
authors.affiliation: College of Chemistry & Materials Engineering, Wenzhou University, Wenzhou 325035, China.
authors.forename: Jiuxi
authors.initials: J
authors.lastname: Chen
authors.forename: Leping
authors.initials: L
authors.lastname: Ye
authors.forename: Weike
authors.initials: W
authors.lastname: Su
mesh_terms: D001577:Benzophenones / Q000138:chemical synthesis* / Q000737:chemistry; D001897:Boronic Acids / Q000737:chemistry*; D002384:Catalysis; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry; D062105:Molecular Docking Simulation; D015394:Molecular Structure; D009570:Nitriles / Q000737:chemistry*; D010165:Palladium / Q000737:chemistry*
chemical_list: D001577:Benzophenones; D001897:Boronic Acids; D007211:Indoles; D009570:Nitriles; C540240:o-aminobenzonitrile; D010165:Palladium