Design and synthesis of 1-glycosyl-4-{N-[(2′-morpholinethoxy)- phenyl]aminomethyl}-1H-1,2,3-triazoles as calcium activators

Abstract

A series of novel 1-glycosyl-4-{N-[(2′-morpholinethoxy)phenyl]aminomethyl}-1H-1,2,3-triazoles was designed and synthesized through a simple and efficient multistep synthetic method in good yields. The 1,2,3-triazole moiety acted as a single disubstituted ring and a linker between carbohydrates(D-glucose, D-galactose, maltose and lactose) and morpholine. The compounds were characterized by 1 H NMR, 13 C NMR and mass spectra(MS). Two different deprotection methods were discussed. The effects of compounds 5a, 5c and 6e on the intracellular calcium ion concentration([Ca 2+ ] i ) in the central neurons of S. exigua were well investigated by calcium imaging technique. The results demonstrated that compound 6e could elevate the calcium concentration in the glial cells, not in the neurons.