Synthesis and biological evaluation of dibenz[ b, f][1,5]oxazocine derivatives for agonist activity at κ-opioid receptor

A short and high yield synthetic route to dibenz[ b, f][1,5]oxazocines has been developed using Pd catalyzed intramolecular cycloamination reaction. Receptor binding assay using [ 125I]-dynorphin demonstrated that one of the derivative, 5b showed selective κ-opioidergic property. A series of dibenzo...

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Veröffentlicht in:	European journal of medicinal chemistry 2011-05, Vol.46 (5), p.1713-1720
Hauptverfasser:	Mitra, Sudipta, Banerjee, Tuhin Suvro, Hota, Sandip K., Bhattacharya, Debleena, Das, Sumantra, Chattopadhyay, Partha
Format:	Artikel
Sprache:	eng
Schlagworte:	Agonist Amination Animals Antineoplastic Agents - chemical synthesis Antineoplastic Agents - chemistry Antineoplastic Agents - pharmacology Aryl amination Binding Sites - drug effects Biological and medical sciences Catalysis Cell Proliferation - drug effects Dibenz[ b, f][1,5]oxazocines Glioma - enzymology Medical sciences Mice Mice, Inbred BALB C Models, Molecular Molecular Structure Neuropharmacology Neurotransmitters. Neurotransmission. Receptors Oxazocines - chemical synthesis Oxazocines - chemistry Oxazocines - pharmacology Palladium - chemistry Palladium catalyst Peptidergic system (neuropeptide, opioid peptide, opiates...). Adenosinergic and purinergic systems Pharmacology. Drug treatments Receptors, Opioid, kappa - agonists Stereoisomerism Structure-Activity Relationship Tumor Cells, Cultured κ-Opioid receptor
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Zusammenfassung:	A short and high yield synthetic route to dibenz[ b, f][1,5]oxazocines has been developed using Pd catalyzed intramolecular cycloamination reaction. Receptor binding assay using [ 125I]-dynorphin demonstrated that one of the derivative, 5b showed selective κ-opioidergic property. A series of dibenzoxazocine derivatives were synthesized which were identified as novel non-peptidic κ-agonist. [Display omitted] ► Synthesis of dibenz[ b, f][1,5]oxazocines. ► Receptor binding assay showing selective κ-opioidergic property. ► Development of a potent κ agonist.
ISSN:	0223-5234 1768-3254
DOI:	10.1016/j.ejmech.2011.02.024