A series of N1- and N2-substituted 4-(2,4-dichlorophenyl)-5-(4-chlorophenyl)-1,2,3-triazoles were regioselectively synthesized to explore the binding motifs of the diaryl-1,2,3-triazole scaffold at CB1 receptors. The N1 analogs were regioselectively constructed via Click chemistry to furnish analogs with modest CB1 receptor affinity (K i < 200 nM). The regioselective N2-alkylation of the 4-(2,4-dichlorophenyl)-5-(4-chlorophenyl)-1,2,3-triazole afforded analogs that exhibited good affinity for CB1 receptors (K i < 100 nM).
- Cannabinoid receptors
- Click chemistry
ASJC Scopus subject areas
- Pharmacology, Toxicology and Pharmaceutics(all)
- Organic Chemistry