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

doi:10.1039/c2sc20248d

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 journal › Article › peer-review

70 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 language	English (US)
Pages (from-to)	2388
Journal	Chemical Science
Volume	3
Issue number	7
DOIs	https://doi.org/10.1039/c2sc20248d
State	Published - 2012

Bibliographical note

KAUST Repository Item: Exported on 2020-10-01
Acknowledgements: This 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.

ASJC Scopus subject areas

General Chemistry

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

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 {\textcopyright} The Royal Society of Chemistry 2012.",

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

note = "KAUST Repository Item: Exported on 2020-10-01 Acknowledgements: This 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.",

year = "2012",

doi = "10.1039/c2sc20248d",

language = "English (US)",

volume = "3",

pages = "2388",

journal = "Chemical Science",

issn = "2041-6520",

publisher = "Royal Society of Chemistry",

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TY - JOUR

T1 - A concise, efficient synthesis of sugar-based benzothiazoles through chemoselective intramolecular C-S coupling

AU - Shen, Chao

AU - Xia, Haijun

AU - Yan, Hua

AU - Chen, Xinzhi

AU - Ranjit, Sadananda

AU - Xie, Xiaoji

AU - Tan, Davin

AU - Lee, Richmond

AU - Yang, Yanmei

AU - Xing, Bengang

AU - Huang, Kuo-Wei

AU - Zhang, Pengfei

AU - Liu, Xiaogang

N1 - KAUST Repository Item: Exported on 2020-10-01 Acknowledgements: This 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.

PY - 2012

Y1 - 2012

N2 - 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.

AB - 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.

UR - http://hdl.handle.net/10754/561989

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DO - 10.1039/c2sc20248d

M3 - Article

SN - 2041-6520

VL - 3

SP - 2388

JO - Chemical Science

JF - Chemical Science

IS - 7

ER -

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

Abstract

Bibliographical note

ASJC Scopus subject areas

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