Synthesis of new mannosyl, galactosyl and glucosyl theophylline nucleosides with potential activity as antagonists of adenosine receptors. DEMA-induced cyclization of glycosylideneiminouracils

The synthesis of d-mannosyl, d-galactosyl and d-glucosyl theophylline nucleosides by diethoxymethyl acetate (DEMA)-induced cyclization of 4-amino-5-glycosylideneimino-1,3-dimethyluracil is reported. 8-Methyltheophylline derivatives of the same sugars were also prepared by Ac2O/H+-induced cyclization of their imine precursors. This approach has allowed β-d-mannopyranosyl-, α-d-galactofuranosyl- and β-d-glucofuranosyltheophylline nucleosides to be synthesized for the first time. The inhibition of specific binding at A1, A2A, A2B and A3 adenosine receptors in the mannose derivatives is also reported.

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