Piperazinyl benzamidines: synthesis and affinity for the delta opioid receptor.
Piperazinyl benzamidines were prepared and found to bind to the rat delta (delta) 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 1.22nM K(i) for the rat delta opioid receptor and ca. 1000 x selectivity relative to the mu opioid subtype.
Nortey
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Drug Discovery Division, R. W. Johnson Pharmaceutical Research Institute, Welsh and McKean Roads, 19477, Spring House, PA, USA. snortey@prius.jnj.com
Baxter
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Codd
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Zhang
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Reitz
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D000818:Animals; D001550:Benzamidines / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism*; D010879:Piperazines / Q000737:chemistry*; D051381:Rats; D017465:Receptors, Opioid, delta / Q000378:metabolism*
D001550:Benzamidines; D010879:Piperazines; D017465:Receptors, Opioid, delta