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

Handle URI:
http://hdl.handle.net/10754/561989
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 ( 0000-0003-1900-2658 ) ; Zhang, Pengfei; Liu, Xiaogang
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.
KAUST Department:
Biological and Environmental Sciences and Engineering (BESE) Division; KAUST Catalysis Center (KCC); Chemical Science Program; Physical Sciences and Engineering (PSE) Division; HCL
Publisher:
Royal Society of Chemistry (RSC)
Journal:
Chemical Science
Issue Date:
2012
DOI:
10.1039/c2sc20248d
Type:
Article
ISSN:
20416520
Sponsors:
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.
Appears in Collections:
Articles; Physical Sciences and Engineering (PSE) Division; Chemical Science Program; KAUST Catalysis Center (KCC); Biological and Environmental Sciences and Engineering (BESE) Division

Full metadata record

DC FieldValue Language
dc.contributor.authorShen, Chaoen
dc.contributor.authorXia, Haijunen
dc.contributor.authorYan, Huaen
dc.contributor.authorChen, Xinzhien
dc.contributor.authorRanjit, Sadanandaen
dc.contributor.authorXie, Xiaojien
dc.contributor.authorTan, Davinen
dc.contributor.authorLee, Richmonden
dc.contributor.authorYang, Yanmeien
dc.contributor.authorXing, Bengangen
dc.contributor.authorHuang, Kuo-Weien
dc.contributor.authorZhang, Pengfeien
dc.contributor.authorLiu, Xiaogangen
dc.date.accessioned2015-08-03T09:35:43Zen
dc.date.available2015-08-03T09:35:43Zen
dc.date.issued2012en
dc.identifier.issn20416520en
dc.identifier.doi10.1039/c2sc20248den
dc.identifier.urihttp://hdl.handle.net/10754/561989en
dc.description.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.en
dc.description.sponsorshipThis 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.en
dc.publisherRoyal Society of Chemistry (RSC)en
dc.titleA concise, efficient synthesis of sugar-based benzothiazoles through chemoselective intramolecular C-S couplingen
dc.typeArticleen
dc.contributor.departmentBiological and Environmental Sciences and Engineering (BESE) Divisionen
dc.contributor.departmentKAUST Catalysis Center (KCC)en
dc.contributor.departmentChemical Science Programen
dc.contributor.departmentPhysical Sciences and Engineering (PSE) Divisionen
dc.contributor.departmentHCLen
dc.identifier.journalChemical Scienceen
dc.contributor.institutionCollege of Material Chemistry and Chemical Engineering, Hangzhou Normal University, Hangzhou 310036, Chinaen
dc.contributor.institutionDepartment of Chemical and Biological Engineering, Zhejiang University, Hangzhou 310027, Chinaen
dc.contributor.institutionDepartment of Chemistry, National University of Singapore, 3 Science Drive 3, Singapore 117543, Singaporeen
dc.contributor.institutionInstitute of Materials Research and Engineering, Agency for Science and Technology and Research, 3 Research Link, Singapore 117602, Singaporeen
dc.contributor.institutionDivision of Chemistry and Biological Chemistry, Nanyang Technological University, Singapore 637371, Singaporeen
kaust.authorTan, Davinen
kaust.authorLee, Richmonden
kaust.authorHuang, Kuo-Weien
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