Piperazinyl benzamidines: Synthesis and affinity for the delta opioid receptor

Piperazinyl benzamidines: Synthesis and affinity for the delta opioid receptor

Piperazinyl benzamidines were prepared and found to bind to the rat delta (δ) opioid receptor. The most active compounds had a N,N-diethylcarboxamido group and a N-benzyl piperazine. The most potent among these was N,N-diethyl-4-[4-(phenylmethyl)-1-piperazinyl][2-(trifluoromethyl)phenyl]iminomethyl]...

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Veröffentlicht in:Bioorganic & medicinal chemistry letters 2001-07, Vol.11 (13), p.1741-1743
Hauptverfasser: Nortey, Samuel O., Baxter, Ellen W., Codd, Ellen E., Zhang, Sui-Po, Reitz, Allen B.
Format: Artikel
Sprache:eng
Schlagworte:
Animals
Benzamidines - chemical synthesis
Benzamidines - chemistry
Benzamidines - metabolism
Biological and medical sciences
Medical sciences
Neuropharmacology
Neurotransmitters. Neurotransmission. Receptors
Peptidergic system (neuropeptide, opioid peptide, opiates...). Adenosinergic and purinergic systems
Pharmacology. Drug treatments
Piperazines - chemistry
Rats
Receptors, Opioid, delta - metabolism
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Zusammenfassung:Piperazinyl benzamidines were prepared and found to bind to the rat delta (δ) opioid receptor. The most active compounds had a N,N-diethylcarboxamido group and a N-benzyl piperazine. The most potent among these was N,N-diethyl-4-[4-(phenylmethyl)-1-piperazinyl][2-(trifluoromethyl)phenyl]iminomethyl]benzamide ( 27) with a 1.22 nM K i for the rat δ opioid receptor and ca. 1000× selectivity relative to the μ opioid subtype. Piperazinyl benzamides such as 27 are potent and selective δ opioid receptor ligands.
ISSN:0960-894X
1464-3405
DOI:10.1016/S0960-894X(01)00272-4