Please use this identifier to cite or link to this item: https://hdl.handle.net/10356/101575
Title: A concise, efficient synthesis of sugar-based benzothiazoles through chemoselective intramolecular C–S coupling
Authors: Shen, Chao
Xia, Haijun
Yan, Hua
Chen, Xinzhi
Ranjit, Sadananda
Xie, Xiaoji
Tan, Davin
Lee, Richmond
Yang, Yanmei
Xing, Bengang
Huang, Kuo-Wei
Zhang, Pengfei
Liu, Xiaogang
Issue Date: 2012
Source: Shen, C., Xia, H., Yan, H., Chen, X., Ranjit, S., Xie, X., et al. (2012). A concise, efficient synthesis of sugar-based benzothiazoles through chemoselective intramolecular C–S coupling. Chemical Science, 3(7), 2388-2393.
Series/Report no.: Chemical science
Abstract: 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.
URI: https://hdl.handle.net/10356/101575
http://hdl.handle.net/10220/11113
DOI: 10.1039/c2sc20248d
Rights: © 2012 The Royal Society of Chemistry.
Fulltext Permission: none
Fulltext Availability: No Fulltext
Appears in Collections:SPMS Journal Articles

Google ScholarTM

Check

Altmetric


Plumx

Items in DR-NTU are protected by copyright, with all rights reserved, unless otherwise indicated.