Synthesis of N-glycoside compounds from phthalimide and 5-nitrobenzimidazole via 1,2-O-sulfinyl derivatives and in vitro cytotoxic activity - Archive ouverte HAL Accéder directement au contenu
Article Dans Une Revue Journal of the Iranian Chemical Society Année : 2020

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

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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).
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hal-03613850 , version 1 (18-03-2022)

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Abdelhafid Benksim, Said Elhizazi, Brahim Lakhrissi, Mohamed Amine, Mohamed Cherkaoui, et al.. Synthesis of N-glycoside compounds from phthalimide and 5-nitrobenzimidazole via 1,2-O-sulfinyl derivatives and in vitro cytotoxic activity. Journal of the Iranian Chemical Society, 2020, 17 (7), pp.1567-1573. ⟨10.1007/s13738-020-01877-3⟩. ⟨hal-03613850⟩
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