Synthesis of N-glycoside compounds from phthalimide and 5-nitrobenzimidazole via 1,2-O-sulfinyl derivatives and in vitro cytotoxic activity

Abstract

An efficient synthesis of 1,2-trans-N-glycosylated derivatives from phthalimide and nitrobenzimidazole via 1,2-O-sulfinyl monosaccharides has been established. Such SN2-type displacements at the anomeric center are stereospecific, giving a single anomer. The reaction was optimized using a polar aprotic solvent and K2CO3 at 80 °C. Phthalimide and nitrobenzimidazole 1,2-trans-N-glycoside derivatives were easily obtained with a free hydroxyl at C-2, which can be further functionalized. The compounds 3d–e displayed a significant cytotoxic activity exceeding 50% of inhibition at 125 μg/Ml against the human cancer cell line (Hep-2).