Synthesis of New Series of 2-C-(β-D-glucopyranosyl)-Pyrimidines and Their Evaluation as Inhibitors of Some Glycoenzymes.

摘要: Despite the substantial interest in C-glycosyl heterocycles as mimetics of biologically active native glycans, appearance C-glycopyranosyl derivatives six-membered heterocycles, both synthetic and biological contexts, is rather scarce. As part our ongoing research program aimed at preparing hitherto barely known 2-C-glycopyranosyl pyrimidines, goal present study was to synthesize new 5-mono- multiply substituted this compound class. Thus, 2-C-(β-D-glucopyranosyl)-5,6-disubstituted-pyrimidin-4(3H)-ones 4-amino-2-C-(β-D-glucopyranosyl)-5,6-disubstituted-pyrimidines were prepared by base-mediated cyclocondensations O-perbenzylated O-unprotected C-(β-D-glucopyranosyl) formamidine hydrochlorides with methylenemalonic acid derivatives. The 2-C-(β-D-glucopyranosyl)-5-substituted-pyrimidines obtained from same amidine precursors upon treatment vinamidinium salts. deprotected these pyrimidines tested inhibitors some glycoenzymes. None them showed inhibitory activity towards glycogen phosphorylase α- β-glucosidase enzymes, but members sets exhibited moderate inhibition against bovine liver β-galactosidase.