A concise, efficient synthesis of sugar-based benzothiazoles through chemoselective intramolecular C-S coupling
KAUST DepartmentBiological and Environmental Sciences and Engineering (BESE) Division
KAUST Catalysis Center (KCC)
Chemical Science Program
Physical Sciences and Engineering (PSE) Division
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AbstractSugar-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. This journal is © The Royal Society of Chemistry 2012.
SponsorsThis study was supported in part by the Science and Technology Plan of Zhejiang Province (No. 2011C24004), the Key-Sci-Tech Innovation Team of Zhejiang Province (No. 2010R50017), the Natural Science Foundation of China (No. 21076052), the Singapore Ministry of Education and the Agency for Science, and Technology and Research (A*STAR). We are also grateful to Prof. J. Zhang for providing the cytotoxicity analysis.
PublisherRoyal Society of Chemistry (RSC)