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A concise, efficient synthesis of sugar-based benzothiazoles through chemoselective intramolecular C-S coupling

Chemical Science, ISSN: 2041-6539, Vol: 3, Issue: 7, Page: 2388-2393
2012
  • 70
    Citations
  • 0
    Usage
  • 19
    Captures
  • 0
    Mentions
  • 0
    Social Media
Metric Options:   Counts1 Year3 Year

Metrics Details

  • Citations
    70
    • Citation Indexes
      70
  • Captures
    19

Article Description

Sugar-based benzothiazoles are a new class of molecules promising for many biological applications. Here, we have synthesized a wide range of sugar-based benzothiazoles from readily accessible glycosyl thioureas by chemoselective, palladium-catalyzed C-S coupling reactions. Corroborated by theoretical calculations, a mechanistic investigation indicates that the coordination to the palladium by a pivaloyl carbonyl group and the presence of intramolecular hydrogen bonding play important roles in the efficiency and chemoselectivity of reaction. These fluorescent glycoconjugates can be observed to readily enter mammalian tumor cells and exhibit potential in vitro antitumor activity. © The Royal Society of Chemistry 2012.

Bibliographic Details

Chao Shen; Haijun Xia; Hua Yan; Pengfei Zhang; Xinzhi Chen; Sadananda Ranjit; Xiaoji Xie; Xiaogang Liu; Davin Tan; Richmond Lee; Kuo Wei Huang; Yanmei Yang; Bengang Xing

Royal Society of Chemistry (RSC)

Chemistry

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