Potent imidazole and triazole CB1 receptor antagonists related to SR141716

Brian Dyck; Val S Goodfellow; Teresa Phillips; Jonathan Grey; Mustapha Haddach; Martin Rowbottom; Gregory S Naeve; Brock Brown; John Saunders

doi:10.1016/j.bmcl.2003.12.068

Potent imidazole and triazole CB1 receptor antagonists related to SR141716

Bioorg Med Chem Lett. 2004 Mar 8;14(5):1151-4. doi: 10.1016/j.bmcl.2003.12.068.

Authors

Brian Dyck¹, Val S Goodfellow, Teresa Phillips, Jonathan Grey, Mustapha Haddach, Martin Rowbottom, Gregory S Naeve, Brock Brown, John Saunders

Affiliation

¹ Departments of Medicinal Chemistry, Pharmacology and Molecular Biology, Neurocrine Biosciences Inc., 10555 Science Center Drive, San Diego, CA 92121, USA.

PMID: 14980654
DOI: 10.1016/j.bmcl.2003.12.068

Abstract

Diarylimidazolecarboxamides and diaryltriazolecarboxamides related to SR141716 were synthesized and tested for binding to the human CB(1) receptor. Suitably substituted imidazoles are comparably potent to the clinical candidate, whereas the analogous triazoles are less so due to the absence of an additional substituent on the azole ring.

MeSH terms

Imidazoles / chemistry
Imidazoles / metabolism*
Piperidines / chemistry
Piperidines / metabolism*
Protein Binding
Pyrazoles / chemistry
Pyrazoles / metabolism*
Receptor, Cannabinoid, CB1 / antagonists & inhibitors*
Receptor, Cannabinoid, CB1 / metabolism*
Rimonabant
Triazoles / chemistry
Triazoles / metabolism*

Substances

Imidazoles
Piperidines
Pyrazoles
Receptor, Cannabinoid, CB1
Triazoles
imidazole
Rimonabant