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

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

Research output: Contribution to journalArticlepeer-review

62 Scopus citations

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. This journal is © The Royal Society of Chemistry 2012.
Original languageEnglish (US)
Pages (from-to)2388
JournalChemical Science
Volume3
Issue number7
DOIs
StatePublished - 2012

ASJC Scopus subject areas

  • Chemistry(all)

Fingerprint

Dive into the research topics of 'A concise, efficient synthesis of sugar-based benzothiazoles through chemoselective intramolecular C-S coupling'. Together they form a unique fingerprint.

Cite this