Redefining the Structure−Activity Relationships of 2,6-Methano-3-benzazocines. 4. Opioid Receptor Binding Properties of 8-[N-(4‘-phenyl)-phenethyl)carboxamido] Analogues of Cyclazocine and Ethylketocycalzocine

The synthesis and evaluation of a series of aryl-containing N-monosubstituted analogues of the lead compound 8-carboxamidocyclazocine were performed to probe a putative hydrophobic binding pocket of opioid receptors. High binding affinity to μ, κ, and δ opioid receptors was observed for the 8-[N-(4‘...

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Veröffentlicht in:	Journal of medicinal chemistry 2006-09, Vol.49 (18), p.5635-5639
Hauptverfasser:	Wentland, Mark P, VanAlstine, Melissa, Kucejko, Robert, Lou, Rongliang, Cohen, Dana J, Parkhill, Amy L, Bidlack, Jean M
Format:	Artikel
Sprache:	eng
Schlagworte:	Animals Biological and medical sciences CHO Cells Cricetinae Cricetulus Cyclazocine - analogs & derivatives Cyclazocine - chemical synthesis Cyclazocine - pharmacology Ethylketocyclazocine - analogs & derivatives Ethylketocyclazocine - chemical synthesis Ethylketocyclazocine - pharmacology Humans Hydrophobic and Hydrophilic Interactions Medical sciences Neuropharmacology Neurotransmitters. Neurotransmission. Receptors Peptidergic system (neuropeptide, opioid peptide, opiates...). Adenosinergic and purinergic systems Pharmacology. Drug treatments Radioligand Assay Receptors, Opioid, delta - drug effects Receptors, Opioid, delta - metabolism Receptors, Opioid, kappa - drug effects Receptors, Opioid, kappa - metabolism Receptors, Opioid, mu - drug effects Receptors, Opioid, mu - metabolism Stereoisomerism Structure-Activity Relationship
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Zusammenfassung:	The synthesis and evaluation of a series of aryl-containing N-monosubstituted analogues of the lead compound 8-carboxamidocyclazocine were performed to probe a putative hydrophobic binding pocket of opioid receptors. High binding affinity to μ, κ, and δ opioid receptors was observed for the 8-[N-(4‘-phenyl)-phenethyl)carboxamido] analogue.
ISSN:	0022-2623 1520-4804
DOI:	10.1021/jm060278n