Discovery of N-(3-(morpholinomethyl)-phenyl)-amides as potent and selective CB2 agonists

Karin Worm, Damian G. Weaver, Rosalyn C. Green, Christopher T. Saeui, Doreen Marie S. Dulay, William M. Barker, Joel A. Cassel, Gabriel J. Stabley, Robert N. DeHaven, Christopher J. LaBuda, Michael Koblish, Bernice L. Brogdon, Steven A. Smith, Roland E. Dolle

Research output: Contribution to journalArticlepeer-review

11 Scopus citations

Abstract

Recently sulfamoyl benzamides were identified as a novel series of cannabinoid receptor ligands. Replacing the sulfonamide functionality and reversing the original carboxamide bond led to the discovery of N-(3-(morpholinomethyl)-phenyl)-amides as potent and selective CB2 agonists. Selective CB2 agonist 31 (Ki = 2.7; CB1/CB2 = 190) displayed robust activity in a rodent model of postoperative pain.

Original languageEnglish
Pages (from-to)5004-5008
Number of pages5
JournalBioorganic and Medicinal Chemistry Letters
Volume19
Issue number17
DOIs
StatePublished - Sep 1 2009

Keywords

  • Antiallodynic activity
  • Cannabinoid CB receptor agonist
  • Metabolic stability
  • Selectivity
  • Structure-activity relationship

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