title: Synthesis and Anti-influenza A Virus Activity of 2,2-Dialkylamantadines and Related Compounds.
abstract: The synthesis of several 2,2-dialkyladamantyl-1-amines through the combination of a Ritter reaction with a Wagner-Meerwein rearrangement from noradamantane alcohols is reported. Several of the novel amines displayed low micromolar activities against several H1N1 influenza virus strains, including the amantadine-resistant A/PuertoRico/8/34 strain. Most of the compounds did not show cytotoxicity for MDCK cells.
authors.affiliation: Laboratori de Química Farmacèutica (Unitat Associada al CSIC), Facultat de Farmàcia, and Institute of Biomedicine (IBUB), Universitat de Barcelona , Av. Diagonal 643, Barcelona E-08028, Spain.
authors.forename: Eva
authors.initials: E
authors.lastname: Torres
authors.affiliation: Laboratori de Química Farmacèutica (Unitat Associada al CSIC), Facultat de Farmàcia, and Institute of Biomedicine (IBUB), Universitat de Barcelona , Av. Diagonal 643, Barcelona E-08028, Spain.
authors.forename: Roser
authors.initials: R
authors.lastname: Fernández
authors.affiliation: Laboratori de Química Farmacèutica (Unitat Associada al CSIC), Facultat de Farmàcia, and Institute of Biomedicine (IBUB), Universitat de Barcelona , Av. Diagonal 643, Barcelona E-08028, Spain.
authors.forename: Stéphanie
authors.initials: S
authors.lastname: Miquet
authors.affiliation: Crystallografia, Mineralogia i Dipòsits Minerals, Universitat de Barcelona , Martí i Franquès s/n, Barcelona E-08028, Spain ; Unitat de Difracció de RX, Centre Científic i Tecnològic de la Universitat de Barcelona (CCiTUB), Universitat de Barcelona , Solé i Sabarís 1-3, Barcelona E-08028, Spain.
authors.forename: Mercè
authors.initials: M
authors.lastname: Font-Bardia
authors.affiliation: Rega Institute for Medical Research, University of Leuven , 3000 Leuven, Belgium.
authors.forename: Evelien
authors.initials: E
authors.lastname: Vanderlinden
authors.affiliation: Rega Institute for Medical Research, University of Leuven , 3000 Leuven, Belgium.
authors.forename: Lieve
authors.initials: L
authors.lastname: Naesens
authors.affiliation: Laboratori de Química Farmacèutica (Unitat Associada al CSIC), Facultat de Farmàcia, and Institute of Biomedicine (IBUB), Universitat de Barcelona , Av. Diagonal 643, Barcelona E-08028, Spain.
authors.forename: Santiago
authors.initials: S
authors.lastname: Vázquez
keywords: M2 channel; Ritter reaction; Wagner−Meerwein rearrangement; amantadine; influenza