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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
  • 2
    Citations
  • 0
    Usage
  • 7
    Captures
  • 0
    Mentions
  • 16
    Social Media
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Metrics Details

  • Citations
    2
  • Captures
    7
  • Social Media
    16
    • Shares, Likes & Comments
      16
      • Facebook
        16

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).

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