Abstract
A library of compounds biased toward opioid receptor antagonist activity was prepared by incorporating N-phenylpropyl-4beta-methyl-5-(3-hydroxyphenyl)morphans as the core scaffold using simultaneous solution phase synthetic methodology. From this library, N-phenylpropyl-4beta-methyl-5-(3-hydroxyphenyl)-7alpha-[3-(1-piperidinyl)propanamido]morphan [(-)-3b] was identified as the first potent and selective kappa opioid receptor antagonist from the 5-phenylmorphan class of opioids.
Publication types
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Research Support, U.S. Gov't, P.H.S.
MeSH terms
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Animals
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Brain / metabolism
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Bridged Bicyclo Compounds, Heterocyclic / chemical synthesis*
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Bridged Bicyclo Compounds, Heterocyclic / chemistry
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Bridged Bicyclo Compounds, Heterocyclic / pharmacology
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CHO Cells
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Combinatorial Chemistry Techniques
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Cricetinae
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Guinea Pigs
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Humans
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In Vitro Techniques
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Ligands
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Morphinans / chemical synthesis*
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Morphinans / chemistry
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Morphinans / pharmacology
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Radioligand Assay
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Rats
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Receptors, Opioid, kappa / antagonists & inhibitors*
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Stereoisomerism
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Structure-Activity Relationship
Substances
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Bridged Bicyclo Compounds, Heterocyclic
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Ligands
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Morphinans
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N-phenylpropyl-4-methyl-5-(3-hydroxyphenyl)-7-(3-(1-piperidinyl)propanamido)morphan
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Receptors, Opioid, kappa