Rico-Gómez Rodrigo, López-Romero J Manuel, Hierrezuelo Jesús, Brea José, Loza M Isabel, Pérez-González Maykel
Dept. de Química Orgánica, Facultad de Ciencias, Universidad de Málaga, 29071 Málaga, Spain.
Carbohydr Res. 2008 Apr 7;343(5):855-64. doi: 10.1016/j.carres.2008.01.011. Epub 2008 Jan 18.
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.
报道了通过乙酸二乙氧基甲酯（DEMA）诱导4-氨基-5-糖基亚胺基-1,3-二甲基尿嘧啶环化合成D-甘露糖基、D-半乳糖基和D-葡萄糖基茶碱核苷。还通过其亚胺前体的Ac(2)O/H⁺诱导环化制备了相同糖类的8-甲基茶碱衍生物。这种方法首次实现了β-D-甘露吡喃糖基、α-D-半乳呋喃糖基和β-D-葡呋喃糖基茶碱核苷的合成。还报道了甘露糖衍生物对A(1)、A(2A)、A(2B)和A(3)腺苷受体特异性结合的抑制作用。
