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, ISSN: 1735-2428, Vol: 17, Issue: 7, Page: 1567-1573
2020
- 2Citations
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Article Description
An efficient synthesis of 1,2-trans-N-glycosylated derivatives from phthalimide and nitrobenzimidazole via 1,2-O-sulfinyl monosaccharides has been established. Such S2-type displacements at the anomeric center are stereospecific, giving a single anomer. The reaction was optimized using a polar aprotic solvent and KCO 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).
Bibliographic Details
http://www.scopus.com/inward/record.url?partnerID=HzOxMe3b&scp=85086282950&origin=inward; http://dx.doi.org/10.1007/s13738-020-01877-3; http://link.springer.com/10.1007/s13738-020-01877-3; http://link.springer.com/content/pdf/10.1007/s13738-020-01877-3.pdf; http://link.springer.com/article/10.1007/s13738-020-01877-3/fulltext.html; https://dx.doi.org/10.1007/s13738-020-01877-3; https://link.springer.com/article/10.1007/s13738-020-01877-3
Springer Science and Business Media LLC
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