Novel pyridine derivatives as potent and selective CB2 cannabinoid receptor agonists

Guo Hua Chu, Christopher T. Saeui, Karin Worm, Damian G. Weaver, Allan J. Goodman, Robert L. Broadrup, Joel A. Cassel, Robert N. DeHaven, Christopher J. LaBuda, Michael Koblish, Bernice Brogdon, Steve Smith, Bertrand Le Bourdonnec, Roland E. Dolle

Research output: Contribution to journalArticle

15 Scopus citations

Abstract

Replacement of the phenyl ring in our previous (morpholinomethyl)aniline carboxamide cannabinoid receptor ligands with a pyridine ring led to the discovery of a novel chemical series of CB2 ligands. Compound 3, that is, 2,2-dimethyl-N-(5-methyl-4-(morpholinomethyl)pyridin-2-yl)butanamide was identified as a potent and selective CB2 agonist exhibiting in vivo efficacy after oral administration in a rat model of neuropathic pain.

Original languageEnglish
Pages (from-to)5931-5935
Number of pages5
JournalBioorganic and Medicinal Chemistry Letters
Volume19
Issue number20
DOIs
StatePublished - Oct 15 2009
Externally publishedYes

Keywords

  • Cannabinoid receptors
  • Pain
  • Pyridine derivatives
  • Selective CB agonists

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    Chu, G. H., Saeui, C. T., Worm, K., Weaver, D. G., Goodman, A. J., Broadrup, R. L., Cassel, J. A., DeHaven, R. N., LaBuda, C. J., Koblish, M., Brogdon, B., Smith, S., Bourdonnec, B. L., & Dolle, R. E. (2009). Novel pyridine derivatives as potent and selective CB2 cannabinoid receptor agonists. Bioorganic and Medicinal Chemistry Letters, 19(20), 5931-5935. https://doi.org/10.1016/j.bmcl.2009.08.063