Synthesis and structure–activity relationships of a new series of 2α-substituted trans-4,5-dimethyl-4-(3-hydroxyphenyl)piperidine as μ-selective opioid antagonists

The synthesis and SAR studies of a series of 2α-substituted trans-4,5-dimethyl-4-(3-hydroxyphenyl)piperidines as novel μ-opioid receptor antagonists are reported. Structure–activity relationships at the 2α-position of the piperidine ring of the trans-4,5-dimethyl-4-(3-hydroxyphenyl)piperidine μ-opio...

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Bibliographic Details
Published in:Bioorganic & medicinal chemistry letters 2006-02, Vol.16 (4), p.864-868
Main Authors: Le Bourdonnec, Bertrand, Goodman, Allan J., Michaut, Mathieu, Ye, Hai-Fen, Graczyk, Thomas M., Belanger, Serge, DeHaven, Robert N., Dolle, Roland E.
Format: Article
Language:English
Subjects:
Antagonist
Biological and medical sciences
Medical sciences
Neuropharmacology
Neurotransmitters. Neurotransmission. Receptors
Opioid
Peptidergic system (neuropeptide, opioid peptide, opiates...). Adenosinergic and purinergic systems
Pharmacology. Drug treatments
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Summary:The synthesis and SAR studies of a series of 2α-substituted trans-4,5-dimethyl-4-(3-hydroxyphenyl)piperidines as novel μ-opioid receptor antagonists are reported. Structure–activity relationships at the 2α-position of the piperidine ring of the trans-4,5-dimethyl-4-(3-hydroxyphenyl)piperidine μ-opioid antagonist series were investigated. This study showed that only small linear alkyl groups (methyl, propyl) are tolerated at the 2α-position of the piperidine ring of this series.
ISSN:0960-894X
1464-3405
DOI:10.1016/j.bmcl.2005.11.010