2. Academic Validation
  3. Synthesis and Anti-influenza A Virus Activity of 2,2-Dialkylamantadines and Related Compounds

Synthesis and Anti-influenza A Virus Activity of 2,2-Dialkylamantadines and Related Compounds

  • ACS Med Chem Lett. 2012 Oct 22;3(12):1065-9. doi: 10.1021/ml300279b.
Eva Torres 1,  Roser Fernández 1,  Stéphanie Miquet 1,  Mercè Font-Bardia 2,  Evelien Vanderlinden 3,  Lieve Naesens 3,  Santiago Vázquez 1
Affiliations

Affiliations

  • 1 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.
  • 2 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.
  • 3 Rega Institute for Medical Research, University of Leuven , 3000 Leuven, Belgium.
PMID: 24900429 DOI: 10.1021/ml300279b
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.

Keywords

M2 channel; Ritter reaction; Wagner−Meerwein rearrangement; amantadine; influenza.

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