(+/-)-4-[(N-allyl-cis-3-methyl-4-piperidinyl)phenylamino]-N,N-diethylben zamide displays selective binding for the delta opiod receptor

F. Ivy Carroll; S. Mascarella; Jason P. Burgess; James B. Thomas; James B. Thomas; Xavier Herault; RB Rothman; Jason P. Burgess; S. Wayne Mascarella; Heng Xu; RB Horel; CM Dersch; Ivy Carroll

(+/-)-4-[(N-allyl-cis-3-methyl-4-piperidinyl)phenylamino]-N,N-diethylben zamide displays selective binding for the delta opiod receptor

Thomas, J., Herault, X., Rothman, RB., Burgess, J., Mascarella, S., Xu, H., Horel, RB., Dersch, CM., & Carroll, F. (1999). (+/-)-4-[(N-allyl-cis-3-methyl-4-piperidinyl)phenylamino]-N,N-diethylben zamide displays selective binding for the delta opiod receptor. Bioorganic and Medicinal Chemistry Letters, 9(20), 3053-3056.

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Abstract

Racemic 4-[(N-allyl-cis-3-methyl-4-piperidinyl)phenylamino]-N,N-diethylbenzamide (3a) was synthesized and found to have good affinity and selectivity for the 6 receptor. These compounds can be viewed as an analog of BW373U86 and SNC-80 where an internal piperazine nitrogen has been transposed with a benzylic carbon. Functionally, 3a behaves as an agonist at the 6 receptor with no measurable stimulation of either the mu or kappa receptor subtypes and was found to be devoid of any measurable amount of antagonist activity for any opioid receptor. A comparison of 3a to SNC-80 and DPDPE in the [S-35]GTP gamma S functional assay suggests that 3a may be more like the peptide DPDPE. (C) 1999 Elsevier Science Ltd. All rights reserved