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. 2012 Dec 15;22(24):7340-4.
doi: 10.1016/j.bmcl.2012.10.081. Epub 2012 Oct 27.

Redefining the Structure-Activity Relationships of 2,6-methano-3-benzazocines. Part 8. High Affinity Ligands for Opioid Receptors in the Picomolar Ki Range: Oxygenated N-(2-[1,1'-biphenyl]-4-ylethyl) Analogues of 8-CAC

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Redefining the Structure-Activity Relationships of 2,6-methano-3-benzazocines. Part 8. High Affinity Ligands for Opioid Receptors in the Picomolar Ki Range: Oxygenated N-(2-[1,1'-biphenyl]-4-ylethyl) Analogues of 8-CAC

Mark P Wentland et al. Bioorg Med Chem Lett. .
Free PMC article

Abstract

N-[2-(4'-methoxy[1,1'-biphenyl]-4-yl)ethyl]-8-CAC (1) is a high affinity (K(i)=0.084 nM) ligand for the μ opioid receptor and served as the lead compound for this study. Analogues of 1 were made in hopes of identifying an SAR within a series of oxygenated (distal) phenyl derivatives. A number of new analogues were made having single-digit pM affinity for the μ receptor. The most potent was the 3',4'-methylenedioxy analogue 18 (K(i)=1.6 pM).

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Figure 1
Figure 1
Scheme 1
Scheme 1
Scheme 2
Scheme 2

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