Synthesis and pharmacological evaluation of several ring-contracted amantadine analogs.
Camps P, Duque MD, Vázquez S, Naesens L, De Clercq E, Sureda FX, López-Querol M, Camins A, Pallàs M, Prathalingam SR, Kelly JM, Romero V, Ivorra D, Cortés D.
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.