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
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container_end_page 948
container_issue 2
container_start_page 942
container_title Bioorganic & medicinal chemistry
container_volume 20
creator 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
description 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.
doi_str_mv 10.1016/j.bmc.2011.11.050
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source MEDLINE; Elsevier ScienceDirect Journals
subjects 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
title Synthesis of benzopolycyclic cage amines: NMDA receptor antagonist, trypanocidal and antiviral activities
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