Synthesis of benzopolycyclic cage amines: NMDA receptor antagonist, trypanocidal and antiviral activities

The synthesis of several 6,7,8,9,10,11-hexahydro-9-methyl-5,7:9,11-dimethano-5H-benzocyclononen-7-amines is reported. Several of them display low micromolar NMDA receptor antagonist and/or trypanocidal activities. Two compounds are endowed with micromolar anti vesicular stomatitis virus activity, wh...

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Veröffentlicht in:	Bioorganic & medicinal chemistry 2012-01, Vol.20 (2), p.942-948
Hauptverfasser:	Torres, Eva, Duque, María D., López-Querol, Marta, Taylor, Martin C., Naesens, Lieve, Ma, Chunlong, Pinto, Lawrence H., Sureda, Francesc X., Kelly, John M., Vázquez, Santiago
Format:	Artikel
Sprache:	eng
Schlagworte:	Amantadine amines Amines - chemical synthesis Amines - chemistry Amines - pharmacology antagonists Antiviral activity Antiviral Agents - chemical synthesis Antiviral Agents - chemistry Antiviral Agents - pharmacology antiviral properties Antivirals Cage compounds chemistry DNA Viruses - drug effects Glutamic acid receptors (ionotropic) Humans N-Methyl-D-aspartic acid receptors NMDA Receptors, N-Methyl-D-Aspartate - antagonists & inhibitors Receptors, N-Methyl-D-Aspartate - metabolism Trypanocidal Agents - chemical synthesis Trypanocidal Agents - chemistry Trypanocidal Agents - pharmacology Trypanosoma Trypanosoma brucei brucei - drug effects Vesicular stomatitis virus Vesiculovirus
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Zusammenfassung:	The synthesis of several 6,7,8,9,10,11-hexahydro-9-methyl-5,7:9,11-dimethano-5H-benzocyclononen-7-amines is reported. Several of them display low micromolar NMDA receptor antagonist and/or trypanocidal activities. Two compounds are endowed with micromolar anti vesicular stomatitis virus activity, while only one compound shows micromolar anti-influenza activity. The anti-influenza activity of this compound does not seem to be mediated by blocking of the M2 protein.
ISSN:	0968-0896 1464-3391
DOI:	10.1016/j.bmc.2011.11.050