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 Ac(2)O/H(+)-induced cyclization of their imine precursors. This approach has allowed beta-D-mannopyranosyl-, alpha-D-galactofuranosyl- and beta-D-glucofuranosyltheophylline nucleosides to be synthesized for the first time. The inhibition of specific binding at A(1), A(2A), A(2B) and A(3) adenosine receptors in the mannose derivatives is also reported.
Rico-Gómez
Rodrigo
R
Dept. de Química Orgánica, Facultad de Ciencias, Universidad de Málaga, 29071 Málaga, Spain. rrico@uma.es
López-Romero
J Manuel
JM
Hierrezuelo
Jesús
J
Brea
José
J
Loza
M Isabel
MI
Pérez-González
Maykel
M
D000085:Acetates / Q000737:chemistry; D001667:Binding, Competitive; D003500:Cyclization; D005690:Galactose / Q000031:analogs & derivatives / Q000138:chemical synthesis / Q000737:chemistry; D005947:Glucose / Q000031:analogs & derivatives / Q000138:chemical synthesis / Q000737:chemistry; D006801:Humans; D007097:Imines / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D008358:Mannose / Q000031:analogs & derivatives / Q000138:chemical synthesis / Q000737:chemistry; D015394:Molecular Structure; D009705:Nucleosides / Q000138:chemical synthesis* / Q000737:chemistry; D058915:Purinergic P1 Receptor Antagonists; D018047:Receptors, Purinergic P1 / Q000737:chemistry; D011994:Recombinant Proteins / Q000737:chemistry; D013806:Theophylline / Q000138:chemical synthesis* / Q000737:chemistry; D014498:Uracil / Q000737:chemistry*
D000085:Acetates; D007097:Imines; D009705:Nucleosides; D058915:Purinergic P1 Receptor Antagonists; D018047:Receptors, Purinergic P1; D011994:Recombinant Proteins; C529223:diethoxymethyl acetate; D014498:Uracil; D013806:Theophylline; D005947:Glucose; D008358:Mannose; D005690:Galactose