Chinese Journal of Organic Chemistry >
Synthesis and Anti-tumor Activity Evaluation of a Novel Series of Dithiocarbamates Bearing 1,2,3-Triazole and [1-Bi(4-fluorophenyl)methyl]piperazine Unit
Received date: 2016-11-28
Revised date: 2017-01-07
Online published: 2017-02-15
Supported by
Project supported by the Sichuan Provincial Department of Science and Technology Support Projects (No. 2015NZ0033) and the Southwest University for Nationalities Students Innovation and Entrepreneurship Training Fund (No. S201510656121).
Sixteen novel dithiocarbamates containing 1,2,3-trizaole and [1-bi(4-fluorophenyl)methyl]piperazine group were prepared via two steps starting from [1-bi(4-fluorophenyl)methyl]piperazine, propargyl bromide, methanedithione and sodium azide, using a very simple catalytic system composed of 5 mol% copper(I) iodide and DMF-H2O (V∶V=1∶1) as solvent at 70 ℃ for 4 h with moderate yield (34%~65%). The structures of the new compounds were characterized by IR, MS, 1H NMR, 13C NMR and elemental analysis. The bioactive assay for the newly prepared compounds manifested that fourteen dithiocarbamate derivatives exhibited good to excellent inhibitory activity against CDC25B in 20 μg/mL (inhibitiory rate up to 97.96%, IC50 value up to 11.55 μg/mL), and six dithiocarbamate derivatives exhibited excellent inhibitory activity against leukemia HL-60 and lung cancer A-549 cell in 40 μmol·L-1 (inhibitiory rate up to 99.99% and 93.91%, respectively; IC50 value up to 12.11 and 22.45 μg/mL, respectively).
Mo Song , Ding Yong , Zhang Gang , Zhang Zhen , Shao Xuebei , Li Qinghan , Yang Xuejun , Chen Feng . Synthesis and Anti-tumor Activity Evaluation of a Novel Series of Dithiocarbamates Bearing 1,2,3-Triazole and [1-Bi(4-fluorophenyl)methyl]piperazine Unit[J]. Chinese Journal of Organic Chemistry, 2017 , 37(4) : 1000 -1008 . DOI: 10.6023/cjoc201611039
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