N,N-dialkyl-4-[(8-azabicyclo[3.2.1]-oct-3-ylidene)phenylmethyl]benzamides, potent, selective delta opioid agonists

John R Carson; Steven J Coats; Ellen E Codd; Scott L Dax; Jung Lee; Rebecca P Martinez; Lou Anne Neilson; Philip M Pitis; Sui-Po Zhang

doi:10.1016/j.bmcl.2004.02.051

N,N-dialkyl-4-[(8-azabicyclo[3.2.1]-oct-3-ylidene)phenylmethyl]benzamides, potent, selective delta opioid agonists

Bioorg Med Chem Lett. 2004 May 3;14(9):2109-12. doi: 10.1016/j.bmcl.2004.02.051.

Authors

John R Carson¹, Steven J Coats, Ellen E Codd, Scott L Dax, Jung Lee, Rebecca P Martinez, Lou Anne Neilson, Philip M Pitis, Sui-Po Zhang

Affiliation

¹ Drug Discovery, Johnson and Johnson Pharmaceutical Research and Development, LLC, Welsh and McKean Roads, PO 776, Spring House, PA 19477-0776, USA. jcarson@prdus.jnj.com

PMID: 15080989
DOI: 10.1016/j.bmcl.2004.02.051

Abstract

A series of N,N-dialkyl-4-(9-aryltropanylidenemethyl)benzamides was prepared. The lead compounds, 15a and 15c, exhibited extremely high affinity for the delta opioid receptor with excellent selectivity versus the micro opioid receptor. They were full agonists at the delta opioid receptor, as assessed by stimulation of GTPgammaS binding, and displayed antinociceptive activity.

MeSH terms

Analgesics, Opioid / chemistry
Analgesics, Opioid / pharmacology*
Benzamides / chemistry
Benzamides / pharmacology*
Guanosine 5'-O-(3-Thiotriphosphate) / metabolism
Receptors, Opioid, delta / agonists*
Structure-Activity Relationship

Substances

Analgesics, Opioid
Benzamides
Receptors, Opioid, delta
Guanosine 5'-O-(3-Thiotriphosphate)