Oxo-bridged isomers of aza-trishomocubane sigma (sigma) receptor ligands: Synthesis, in vitro binding, and molecular modeling.
Isomeric oxo-bridged analogs of aza-trishomocubane sigma (sigma) receptor ligands were synthesized and shown to display a reduced affinity for the sigma receptor. In the case of phenethyl derivative 4, there was a concomitant introduction of high-affinity for the alpha(2C) adrenergic receptor, and moderate affinity for the dopamine transporter. Molecular modeling was undertaken to rationalize these results.
Banister
Samuel D
SD
School of Chemistry, University of Sydney, NSW 2006, Australia.
Moussa
Iman A
IA
Jordan
Meredith J T
MJ
Coster
Mark J
MJ
Kassiou
Michael
M
D001372:Aza Compounds / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D015195:Drug Design; D007536:Isomerism; D008024:Ligands; D008958:Models, Molecular; D008968:Molecular Conformation; D011485:Protein Binding; D018341:Receptors, Adrenergic, alpha-2 / Q000737:chemistry / Q000378:metabolism; D017480:Receptors, sigma / Q000737:chemistry* / Q000378:metabolism; D013329:Structure-Activity Relationship
D001372:Aza Compounds; D008024:Ligands; D018341:Receptors, Adrenergic, alpha-2; D017480:Receptors, sigma