Synthesis of N-glycoside compounds from phthalimide and 5-nitrobenzimidazole via 1,2-O-sulfinyl derivatives and in vitro cytotoxic activity
Résumé
An efficient synthesis of 1,2-trans-N-glycosylated derivatives from phthalimide and nitrobenzimidazole via 1,2-O-sulfinyl monosaccharides has been established. Such S(N)2-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 degrees 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 mu g/Ml against the human cancer cell line (Hep-2).