N-Acridin-9-yl-butane-1,4-diamine derivatives: high-affinity ligands of the alpha2delta subunit of voltage gated calcium channels

A series of N-acridin-9-yl-butane-1,4-diamines were found to be high-affinity ligands of the alpha(2)delta subunit of voltage gated calcium channels. The SAR studies of butane-1,4-diamine side chain resulted in the identification of compound 10 (IC(50)=9 nM), which is more potent than gabapentin (IC...

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Bibliographic Details
Published in:Bioorganic & medicinal chemistry letters 2004-04, Vol.14 (8), p.1913-1916
Main Authors: Lim, Jongwon, Stock, Nicholas, Pracitto, Richard, Boueres, Julia K, Munoz, Benito, Chaudhary, Ashok, Santini, Angelina M, Orr, Karia, Schaffhauser, Hervé, Bezverkov, Robert E, Aiyar, Jayashree, Venkatraman, Shankar
Format: Article
Language:English
Subjects:
Acetates - pharmacology
Amines
Binding, Competitive - drug effects
Calcium Channels - drug effects
Calcium Channels - physiology
Cyclohexanecarboxylic Acids
Diamines - chemical synthesis
Diamines - chemistry
Diamines - pharmacology
gamma-Aminobutyric Acid
Ligands
Molecular Structure
Protein Binding - drug effects
Protein Binding - physiology
Protein Subunits - drug effects
Protein Subunits - physiology
Structure-Activity Relationship
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Summary:A series of N-acridin-9-yl-butane-1,4-diamines were found to be high-affinity ligands of the alpha(2)delta subunit of voltage gated calcium channels. The SAR studies of butane-1,4-diamine side chain resulted in the identification of compound 10 (IC(50)=9 nM), which is more potent than gabapentin (IC(50)=27 nM). Partial saturation of the acridine ring was also pursued and provided a compound with higher binding affinity than 1.
ISSN:0960-894X