Chin. J. Org. Chem. ›› 2017, Vol. 37 ›› Issue (4): 1000-1008.DOI: 10.6023/cjoc201611039 Previous Articles     Next Articles

Notes

含1-[4-二(4-氟苯)甲基]哌嗪及1,2,3-三唑官能团的二硫代氨基甲酸酯的合成及抗肿瘤活性研究

莫松, 丁勇, 张刚, 张震, 杓学蓓, 李清寒, 杨学军, 陈峰   

  1. 西南民族大学化学与环境保护工程学院 成都 610041
  • 收稿日期:2016-11-28 修回日期:2017-01-07 出版日期:2017-04-25 发布日期:2017-02-15
  • 通讯作者: 李清寒 E-mail:lqhchem@163.com
  • 基金资助:

    四川省科技厅科技支撑计划(No.2015NZ0033)、西南民族大学研究生创新基金(No.CX2016SZ063)资助项目.

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

Mo Song, Ding Yong, Zhang Gang, Zhang Zhen, Shao Xuebei, Li Qinghan, Yang Xuejun, Chen Feng   

  1. College of Chemistry and Environmental Protection Engineering, Southwest University for Nationalities, Chengdu 610041
  • Received:2016-11-28 Revised:2017-01-07 Online:2017-04-25 Published:2017-02-15
  • Contact: 10.6023/cjoc201611039 E-mail:lqhchem@163.com
  • 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 (VV=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).

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