title: Synthesis of 5-halogenated 1,2,3-triazoles under stoichiometric Cu(I)-mediated azide-alkyne cycloaddition (CuAAC or 'Click Chemistry').
abstract: Glucosylated heterocycles have been identified as potent inhibitors of glycogen phosphorylase (GP), a biomolecular target for the treatment of hyperglycemia and therefore type 2 diabetes. Several glucosylated triazoles have been evaluated as GP inhibitors and additional structures are being considered in the present study with the introduction of a substituent at the 5-position of the triazole ring. The 1,3-dipolar cycloaddition of azide and alkyne using stoichiometric amounts of Cu(I) halides favored the formation of the 5-halogenated 1,2,3-triazoles. The influence of the copper halide introduced (CuI, CuBr, or CuCl) provided different results and more specifically for the CuCl system which afforded a dimeric 5,5'-bistriazole in good yield (56%) as evidenced by crystallographic data.
authors.affiliation: Institut de Chimie et Biochimie Moléculaires et Supramoléculaires, Laboratoire de Chimie Organique 2-Glycochimie, UMR 5246, CNRS, Université Claude Bernard Lyon 1, Villeurbanne, France.
authors.forename: David
authors.initials: D
authors.lastname: Goyard
authors.forename: Jean-Pierre
authors.initials: JP
authors.lastname: Praly
authors.forename: Sébastien
authors.initials: S
authors.lastname: Vidal
mesh_terms: D000480:Alkynes / Q000737:chemistry*; D001386:Azides / Q000737:chemistry*; D002384:Catalysis; D057930:Click Chemistry; D003300:Copper / Q000737:chemistry*; D018360:Crystallography, X-Ray; D061565:Cycloaddition Reaction; D004791:Enzyme Inhibitors / Q000138:chemical synthesis*; D024981:Glycogen Phosphorylase / Q000037:antagonists & inhibitors; D054879:Halogenation; D006801:Humans; D007004:Hypoglycemic Agents / Q000138:chemical synthesis*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D013237:Stereoisomerism; D014230:Triazoles / Q000138:chemical synthesis*
chemical_list: D000480:Alkynes; D001386:Azides; D004791:Enzyme Inhibitors; D007004:Hypoglycemic Agents; D014230:Triazoles; D003300:Copper; D024981:Glycogen Phosphorylase