Quaternary ammonium 3-(aminoethoxy)pyridines as antinociceptive agents

Quaternization via N-methylation of the terminal amines of a series of 3-(dialkylaminoethoxy)pyridines resulted in analogues that displayed up to 50–60-fold enhanced affinity for nicotinic acetylcholinergic (nACh) receptors. Several of these compounds displayed antinociceptive properties in mice usi...

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Veröffentlicht in:Bioorganic & medicinal chemistry letters 2003-09, Vol.13 (17), p.2917-2920
Hauptverfasser: Simsek, Rahime, Chang-Fong, Jean, Lee, Mase, Dukat, Malgorzata, Imad Damaj, M., Martin, Billy R., Glennon, Richard A.
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Sprache:eng
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Zusammenfassung:Quaternization via N-methylation of the terminal amines of a series of 3-(dialkylaminoethoxy)pyridines resulted in analogues that displayed up to 50–60-fold enhanced affinity for nicotinic acetylcholinergic (nACh) receptors. Several of these compounds displayed antinociceptive properties in mice using the tail-flick assay and serve as possible leads for the development of novel analgesic agents. Compound 2 ( K i=0.5 nM) was one of several quaternary amines shown to bind at nicotinic acetylcholinergic receptors with high affinity. Antinociceptive action (mouse tail-flick assay) was evident following either subcutaneous or intrathecal administration of 2.
ISSN:0960-894X
1464-3405
DOI:10.1016/S0960-894X(03)00585-7