Synthesis of N4-aryl-β-D-glucopyranosylcytosines: a methodology study


Mamais M, Kouloumoundra V, Smyrli E, Grammatopoulos P, Chrysina ED, Gimisis T. Synthesis of N4-aryl-β-D-glucopyranosylcytosines: a methodology study. Tetrahedron Lett. [Internet]. 2015;56:5549–5552.


© 2015 Elsevier Ltd. All rights reserved.A number of leaving groups, including arylsulfonates, triazoles, 3-nitrotriazoles, and tetrazoles, have been studied for the substitution reaction by aryl and alkyl amines at the 4-position of $\beta$-D-glucopyranosyluracils. Examination of the stability, ease of purification and reactivity in the substitution reaction led to a number of optimized conditions with the most convenient involving substitution of triazole derivatives under microwave conditions in the presence of silica gel. Under these conditions, a number of N4-aryl-substituted $\beta$-D-glucopyranosylcytosines were prepared as potential inhibitors of glycogen phosphorylase, a molecular target for type-2 diabetes mellitus.

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