Abstract:
:Targeted structural modifications have led to a novel type of buprenorphine-derived opioid receptor ligand displaying an improved selectivity profile for the μ-OR subtype. On this basis, it is shown that phenylazocarboxamides may serve as useful bioisosteric replacements for the widely occurring cinnamide units, without loss of OR binding affinity or subtype selectivity. This study further includes functional experiments pointing to weak partial agonist properties of the novel μ-OR ligands, as well as docking and metabolism experiments. Finally, the unique bifunctional character of phenylazocarboxylates, herein serving as precursors for the azocarboxamide subunit, was exploited to demonstrate the accessibility of an 18 F-fluorinated analogue.
journal_name
ChemMedChemjournal_title
ChemMedChemauthors
Krüll J,Fehler SK,Hofmann L,Nebel N,Maschauer S,Prante O,Gmeiner P,Lanig H,Hübner H,Heinrich MRdoi
10.1002/cmdc.202000180subject
Has Abstractpub_date
2020-07-03 00:00:00pages
1175-1186issue
13eissn
1860-7179issn
1860-7187journal_volume
15pub_type
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