N-substituted-1,2,3-triazoles: Synthesis, characterization and evaluation as cannabinoid ligands

Abstract

A series of new N1-, N2-and N3-substituted 1,2,3-triazole derivatives has been synthesized by cycloaddition of butyltin azide with substituted alkynes followed by a N-alkylation reaction. The regioisomers have been isolated and characterized using NMR techniques. GIAO/B3LYP calculations of the absolute shieldings have been performed to verify the assignments and so the structures have been unequivocally identified. The proportion in which the three isomers are obtained corresponds with the relative order of stability indicated by the energy values calculated at the B3LYP level. CB1 cannabinoid receptor binding assays have been performed but none of the compounds showed significant activity. © ARKAT USA, Inc.