title: Synthesis of 7-alkylidene-7,12-dihydroindolo[3,2-d]benzazepine-6-(5H)-ones (7-alkylidene-paullones) by N-cyclization-oxidative Heck cascade and characterization as sirtuin modulators.
abstract: An extension of our reported protocol to benzofused heterocyclic derivatives (benzofurans, indoles, isochromeneimines), involving a palladium-induced cascade of N-cyclization and oxidative Heck reactions of o-alkynylanilines, has allowed the preparation of indolobenzazepinones (paullones) with an alkylidene group at C7 in just 3-4 steps from ortho-iodoanilines. Some of these compounds behave as Sirt1 activators in biochemical assays.
authors.affiliation: Departamento de Química Orgánica, Facultad de Química (CINBIO) and Instituto de Investigación Biomédica de Vigo (IBIV), Universidade de Vigo, Lagoas-Marcosende, 36310 Vigo, Spain. rar@uvigo.es qolera@uvigo.es.
authors.forename: J G
authors.initials: JG
authors.lastname: Denis
authors.forename: G
authors.initials: G
authors.lastname: Franci
authors.forename: L
authors.initials: L
authors.lastname: Altucci
authors.forename: J M
authors.initials: JM
authors.lastname: Aurrecoechea
authors.forename: Á R
authors.initials: ÁR
authors.lastname: de Lera
authors.forename: R
authors.initials: R
authors.lastname: Álvarez
mesh_terms: D001552:Benzazepines / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D003500:Cyclization; D006801:Humans; D007211:Indoles / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D010084:Oxidation-Reduction; D056564:Sirtuin 1 / Q000737:chemistry / Q000378:metabolism*; D013329:Structure-Activity Relationship; D020298:U937 Cells
chemical_list: D001552:Benzazepines; D007211:Indoles; C447939:SIRT1 protein, human; D056564:Sirtuin 1