Bioisosteric replacement of the hydrazide pharmacophore of the cannabinoid-1 receptor antagonist SR141716A. Part I: potent, orally-active 1,4-disubstituted imidazoles.

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Dow RL, Hadcock JR, Scott DO, Schneider SR, Paight ES, Iredale PA, Carpino PA, Griffith DA, Hammond M, Dasilva-Jardine P

Bioisosteric replacement of the hydrazide pharmacophore of the cannabinoid-1 receptor antagonist SR141716A. Part I: potent, orally-active 1,4-disubstituted imidazoles.

Bioorg Med Chem Lett. 2009 Sep 15;19(18):5351-4. doi: 10.1016/j.bmcl.2009.07.130. Epub 2009 Aug 6.

PubMed ID

19683918 [ View in PubMed

]

Abstract

A new series of CB(1) receptor antagonists incorporating an imidazole-based isosteric replacement for the hydrazide moiety of rimonabant (SR141716) is disclosed. Members of this imidazole series possess potent/selective binding to the rCB(1) receptor and exhibit potent hCB(1) functional activity. Isopropyl analog 9a demonstrated activity in the tetrad assay and was orally-active in a food intake model.

DrugBank Data that Cites this Article

Binding Properties

Drug	Target	Property	Measurement	pH	Temperature (°C)
Rimonabant	Cannabinoid receptor 1	Ki (nM)	1.6	N/A	N/A	Details