Journal
CHINESE JOURNAL OF ORGANIC CHEMISTRY
Volume 41, Issue 7, Pages 2723-2734Publisher
SCIENCE PRESS
DOI: 10.6023/cjoc202012047
Keywords
tegafur; diaryl disulfides (diselenides); unsymmetrical sulfides (selenides); antitumor activity; apoptosis
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Funding
- National Natural Science Foundation of China [21802093]
- Scientific and Technological Innovation Programs of Higher Education Institutions in Shanxi Province [2019L0408]
- PhD Start-up Foundation of Shanxi Medical University [03201501]
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A series of novel aryl (N-3-tegafluoroalkyl) thio- and seleno-ether derivatives were efficiently synthesized by multiple-step synthesis methods, and their structures were confirmed by NMR and MS. These compounds exhibited better antitumor activities than tegafur, likely through inducing apoptosis to inhibit the growth of tumor cells.
Tegafur, as a raw material, reacted with chloroalkyl alcohols to give the intermediate N-hydroxyalkyl tegafur, then which reacted with p-toluenesulfonyl chloride to obtain tegafluoroalkyl sulfonate. A series of novel aryl (N-3-tegafluoroalkyl) thio- and seleno-ether derivatives were efficiently synthesized by the reaction of tegafluoroalkyl sulfonate with diaryl disulfides or diselenides under binuclear titanium(IV) salophen perfluorobutanesulfonate/zinc catalytic system. Their structures of the target products were confirmed by H-1 NMR, C-13 NMR and HRMS. Their antitumor activities were evaluated by colorectal carcinoma HCT116 cells and gastric carcinoma SGC-7901 cells. The preliminary bioassay results showed that most target compounds had more antitumor activities than tegafur. Moreover, HCT116 cells staining experiments (DAPI) and quantitative determination by flow cytometry indicated that the growth inhibition was associated with the induction of apoptosis. In addition, organic sulfur (selenium) tegafur derivatives had lower toxicity than tegafur on human embryonic kidney HEK 293 cells.
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