Synthesis and pharmacological evaluation of several ring-contracted amantadine analogs

  • Bioorg Med Chem. 2008 Dec 1;16(23):9925-36. doi: 10.1016/j.bmc.2008.10.028.
Pelayo Camps  1 ,  María D Duque ,  Santiago Vázquez ,  Lieve Naesens ,  Erik De Clercq ,  Francesc X Sureda ,  Marta López-Querol ,  Antoni Camins ,  Mercè Pallàs ,  S Radhika Prathalingam ,  John M Kelly ,  Vanessa Romero ,  Dolores Ivorra ,  Diego Cortés
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.
PMID: 18954995 DOI: 10.1016/j.bmc.2008.10.028
Abstract

The synthesis of several (3-noradamantyl)amines, [(3-noradamantyl)methyl]amines, (3,7-dimethyl-1-bisnoradamantyl)amines, and [(3,7-dimethyl-1-bisnoradamantyl)methyl]amines is reported. They were evaluated against a wide range of viruses and one of them inhibited the cytopathicity of influenza A virus at a concentration similar to that of amantadine. Several of the new polycyclic amines show an interesting activity as NMDA Receptor antagonists. A rimantadine analogue displayed significant trypanocidal activity. Moreover, to further characterize the pharmacology of these compounds, their effects on dopamine uptake were also assessed.