Article

Synthesis and biological characterization of 3-substituted-1H-indoles as ligands of GluN2B-containing N-methyl-D-aspartate receptors.

Dipartimento Farmaco-Chimico, Università di Messina, Viale Annunziata, I-98168 Messina, Italy.
Journal of Medicinal Chemistry (impact factor: 4.8). 11/2011; 54(24):8702-6. DOI:10.1021/jm2008002 pp.8702-6
Source: PubMed

ABSTRACT As an extension of our studies, novel indole derivatives were rationally designed and synthesized as ligands targeted to GluN2B/NMDA receptors. The 2-(4-benzylpiperidin-1-yl)-1-(6-hydroxy-1H-indol-3-yl)ethanone (4i) and 1-(4-benzylpiperidin-1-yl)-2-(6-hydroxy-1H-indol-3-yl)ethane-1,2-dione (6i) showed high binding affinity in [3H]ifenprodil displacement assay. By computational studies, we suggested the hypothetical interactions playing a significant role during the binding process. However, in functional and in vivo studies the most potent compound 4i did not show any activity whereas it displayed relevant affinity toward the σ2 receptor.

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Keywords

[3H]ifenprodil displacement assay
 
binding affinity
 
binding process
 
computational studies
 
GluN2B/NMDA receptors
 
hypothetical interactions
 
novel indole derivatives
 
potent compound 4i
 
vivo studies
 
σ2 receptor