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Synthesis 2011(22): 3635-3638  
DOI: 10.1055/s-0031-1260252
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

A New Synthesis of Cytotoxic Thiosulfonates and the First Synthesis of Deuterated Thiosulfonates

Feng Gaoa, Huiyuan Zhaib, Meina Jinb, Guobiao Chua, Hongquan Duanb, Chunbao Li*a
a Department of Chemistry, College of Science, Tianjin University, Tianjin 300072, P. R. of China
Fax: +86(22)27403475; e-Mail: lichunbao@tju.edu.cn ;
b School of Pharmaceutical Science, Research Center of Basic Medical Sciences, Tianjin Medical University, Tianjin 300070, P. R. of China
Further Information

Publication History

Received 12 July 2011
Publication Date:
05 October 2011 (online)

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Abstract

A new synthesis of thiosulfonates starting from thiophenols and cyanuric chloride activated dimethyl sulfoxide is reported herein. Although the yields of the reactions are moderate, this method enables the incorporation of the SCD3 group of dimethyl sulfoxide-d 6 into thiosulfonates. This is the first synthesis of deuterated thiosulfonates with a labeling purity above 99%. In addition, the cytotoxicity of the thiosulfonates is reported for the first time.

Key words

thiols - esterification - sulfoxides - cytotoxicity - thiosulfonates

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MDA-MB-231 is a type of human breast cancer cell. A549 is a type of human lung cancer cell. They were both supported by the Department of Immunology, Tianjin Medical University. The data for the concentrations and the inhibition are listed in the Supporting Information.