Citation: 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 shu

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

College of Chemistry and Environmental Protection Engineering, Southwest University for Nationalities, Chengdu 610041

Corresponding author: Li Qinghan, lqhchem@163.com
Received Date: 28 November 2016
Revised Date: 7 January 2017

Fund Project: the Southwest University for Nationalities Students Innovation and Entrepreneurship Training Fund S201510656121the Sichuan Provincial Department of Science and Technology Support Projects 2015NZ0033

Figures(1)

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).
- 1-[bi (4-fluorophenyl) methyl]piperazine,
- 1, 2, 3-trizaole,
- carbodithioate,
- organic synthesis,
- antitumor activity
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