Synthesis and SAR studies of 3-phenoxypropyl piperidine analogues as ORL1 (NOP) receptor agonists

A series of potent and soluble ORL1 agonists was prepared and evaluated. Compound 41 showed antinociceptive properties in mouse formalin paw test (ED 50 = 1.07 μmol/kg). A series of 3-phenoxypropyl piperidine analogues have been discovered as novel ORL1 receptor agonists. Structure–activity relation...

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Bibliographic Details
Published in:Bioorganic & medicinal chemistry letters Vol. 15; no. 3; pp. 589 - 593
Main Authors: Palin, Ronald, Barn, David R., Clark, John K., Cottney, Jean E., Cowley, Phillip M., Crockatt, Marc, Evans, Louise, Feilden, Helen, Goodwin, Richard R., Griekspoor, Frank, Grove, Simon J.A., Houghton, Andrea K., Jones, Philip S., Morphy, Richard J., Smith, Alasdair R.C., Sundaram, Hardy, Vrolijk, David, Weston, Mark A., Wishart, Grant, Wren, Paul
Format: Journal Article
Language:English
Published: Oxford Elsevier Ltd 01.02.2005
Elsevier
Subjects:
Analgesia
Analgesics
Animals
Biological and medical sciences
CHO Cells
Cricetinae
Cyclic AMP - biosynthesis
Drug Design
Humans
Hydrophobic and Hydrophilic Interactions
Inhibitory Concentration 50
Male
Medical sciences
Mice
Neuropharmacology
Nociception
Opioid
ORL1
Pharmacology. Drug treatments
Piperidines - chemical synthesis
Piperidines - pharmacology
Receptors, Opioid - agonists
Structure-Activity Relationship
Transfection
Vas Deferens
Nociception
Opioid
Analgesia
ORL1
Agonist
Intravenous administration
Rodentia
Selectivity
In vitro
In vivo
Vertebrata
Mammalia
Analgesic
Structure activity relation
Mouse
Benzimidazole derivatives
N/OFQ receptor
Animal
Piperidine derivatives
Chemical synthesis
ISSN:0960-894X, 1464-3405
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Summary:A series of potent and soluble ORL1 agonists was prepared and evaluated. Compound 41 showed antinociceptive properties in mouse formalin paw test (ED 50 = 1.07 μmol/kg). A series of 3-phenoxypropyl piperidine analogues have been discovered as novel ORL1 receptor agonists. Structure–activity relationships have been explored around the 3-phenoxypropyl region with several potent and selective analogues identified.
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ISSN:0960-894X
1464-3405
DOI:10.1016/j.bmcl.2004.11.049