title: Nucleophilic Substitution of Hydrogen Facilitated by Quinone Methide Moieties in Benzo[cd]azulen-3-ones.
abstract: The built-in o- and p-QM (QM = quinone methide) moieties in benzo[cd]azulen-3-ones account for an easy switch between the bridged 10π- and 6π-aromatic systems in organic synthesis. We report conjugate additions, oxidative nucleophilic substitutions of hydrogen, and reversible Michael additions under very mild conditions. In the presence of thiol nucleophiles, the protonated σH-adducts could be isolated and characterized. The typical preference for either the o- or p-QM moiety led to high regioselectivity. Furthermore, the inhibitory potency of the novel benzo[cd]azulenes against the human Pim-1 kinase was evaluated.
authors.affiliation: Drug Research Program, Division of Pharmaceutical Chemistry and Technology, Faculty of Pharmacy, University of Helsinki , P.O. Box 56, Viikinkaari 5 E, FI-00014 Helsinki, Finland.
authors.forename: Alexandros
authors.initials: A
authors.lastname: Kiriazis
authors.affiliation: Drug Research Program, Division of Pharmaceutical Chemistry and Technology, Faculty of Pharmacy, University of Helsinki , P.O. Box 56, Viikinkaari 5 E, FI-00014 Helsinki, Finland.
authors.forename: Ingo B
authors.initials: IB
authors.lastname: Aumüller
authors.affiliation: Drug Research Program, Division of Pharmaceutical Chemistry and Technology, Faculty of Pharmacy, University of Helsinki , P.O. Box 56, Viikinkaari 5 E, FI-00014 Helsinki, Finland.|Department of Biology, University of Turku , Vesilinnantie 5, FI-20014 Turku, Finland.
authors.forename: Ralica
authors.initials: R
authors.lastname: Arnaudova
authors.affiliation: Health Sciences Research Centre, University of Beira Interior , Av. Infante D. Henrique, 6200-506 Covilhã, Portugal.
authors.forename: Vanessa
authors.initials: V
authors.lastname: Brito
authors.affiliation: Technische Universität Chemnitz, Fakultät für Naturwissenschaften, Institut für Chemie , D-09107 Chemnitz, Germany.
authors.forename: Tobias
authors.initials: T
authors.lastname: Rüffer
authors.affiliation: Technische Universität Chemnitz, Fakultät für Naturwissenschaften, Institut für Chemie , D-09107 Chemnitz, Germany.
authors.forename: Heinrich
authors.identifier: 0000-0001-9744-7906
authors.initials: H
authors.lastname: Lang
authors.affiliation: Health Sciences Research Centre, University of Beira Interior , Av. Infante D. Henrique, 6200-506 Covilhã, Portugal.|Centre for Neuroscience and Cell Biology , 3004-504 Coimbra, Portugal.
authors.forename: Samuel M
authors.initials: SM
authors.lastname: Silvestre
authors.affiliation: Department of Biology, University of Turku , Vesilinnantie 5, FI-20014 Turku, Finland.
authors.forename: Päivi J
authors.initials: PJ
authors.lastname: Koskinen
authors.affiliation: Drug Research Program, Division of Pharmaceutical Chemistry and Technology, Faculty of Pharmacy, University of Helsinki , P.O. Box 56, Viikinkaari 5 E, FI-00014 Helsinki, Finland.
authors.forename: Jari
authors.identifier: 0000-0003-0370-7653
authors.initials: J
authors.lastname: Yli-Kauhaluoma