8-aminocyclazocine analogues : Synthesis and structure-activity relationships

Opioid binding affinities were assessed for a series of cyclazocine analogues where the prototypic 8-OH substituent of cyclazocine was replaced by amino and substituted-amino groups. For mu and kappa opioid receptors, secondary amine derivatives having the (2R,6R,11R)-configuration had the highest a...

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Bibliographic Details
Published in:Bioorganic & medicinal chemistry letters 2000-01, Vol.10 (2), p.183-187
Main Authors: WENTLAND, M. P, GUOYOU XU, CIOFFI, C. L, YINGCHUN YE, WENHU DUAN, COHEN, D. J, COLASURDO, A. M, BIDLACK, J. M
Format: Article
Language:English
Subjects:
Analgesics - chemical synthesis
Analgesics - pharmacology
Animals
Benzeneacetamides
Binding, Competitive
Biological and medical sciences
Brain - drug effects
Cyclazocine - analogs & derivatives
Cyclazocine - chemistry
Enkephalin, Ala-MePhe-Gly- - metabolism
Guinea Pigs
Medical sciences
Molecular Structure
Naltrexone - analogs & derivatives
Naltrexone - metabolism
Narcotic Antagonists
Neuropharmacology
Neurotransmitters. Neurotransmission. Receptors
Peptidergic system (neuropeptide, opioid peptide, opiates...). Adenosinergic and purinergic systems
Pharmacology. Drug treatments
Pyrrolidines - metabolism
Receptors, Opioid - agonists
Stereoisomerism
Structure-Activity Relationship
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Summary:Opioid binding affinities were assessed for a series of cyclazocine analogues where the prototypic 8-OH substituent of cyclazocine was replaced by amino and substituted-amino groups. For mu and kappa opioid receptors, secondary amine derivatives having the (2R,6R,11R)-configuration had the highest affinity. Most targets were efficiently synthesized from the triflate of cyclazocine or its enantiomers using Pd-catalyzed amination procedures.
ISSN:0960-894X
1464-3405
DOI:10.1016/S0960-894X(99)00670-8