1387526-41-1Relevant articles and documents
Deconstructing 14-phenylpropyloxymetopon: Minimal requirements for binding to mu opioid receptors
Stavitskaya, Lidiya,Shim, Jihyun,Healy, Jason R.,Matsumoto, Rae R.,MacKerell Jr., Alexander D.,Coop, Andrew
, p. 4556 - 4563 (2012)
A series of phenylpropyloxyethylamines and cinnamyloxyethylamines were synthesized as deconstructed analogs of 14-phenylpropyloxymetopon and analyzed for opioid receptor binding affinity. Using the Conformationally Sampled Pharmacophore modeling approach, we discovered a series of compounds lacking a tyrosine mimetic, historically considered essential for μ opioid binding. Based on the binding studies, we have identified the optimal analogs to be N-methyl-N-phenylpropyl-2-(3-phenylpropoxy)ethanamine, with 1520 nM, and 2-(cinnamyloxy)-N-methyl-N-phenethylethanamine with 1680 nM affinity for the μ opioid receptor. These partial opioid structure analogs will serve as the novel lead compounds for future optimization studies.