Chin. J. Org. Chem. ›› 2013, Vol. 33 ›› Issue (11): 2384-2390.DOI: 10.6023/cjoc201306035 Previous Articles     Next Articles



王盟盟, 段迎超, 叶先炜, 任景丽, 余斌, 张恩, 刘宏民   

  1. 郑州大学药学院 郑州 450001
  • 收稿日期:2013-06-21 修回日期:2013-07-07 发布日期:2013-07-11
  • 通讯作者: 刘宏民
  • 基金资助:

    国家自然科学基金(Nos. 81172937,U1204206)、教育部博士点新教师基金(No. 20114101120013)和中国博士后科学基金(Nos. 20100480857,201104402)资助项目.

Design, Synthesis and Antitumor Study of Novel 1,4-Bispiperazine-carbodithioic Acid [1-Substituted-(1,2,3-triazole)-4]-methyl Esters

Wang Mengmeng, Duan Yingchao, Ye Xianwei, Ren Jingli, Yu Bin, Zhang En, Liu Hongmin   

  1. School of Pharmaceutical Sciences, Zhengzhou University, Zhengzhou 450001
  • Received:2013-06-21 Revised:2013-07-07 Published:2013-07-11
  • Supported by:

    Project supported by the National Natural Science Foundation of China (Nos. 81172937, U1204206), the New Teachers’ Fund for Doctor Stations, Ministry of Education (No. 20114101120013) and the National Science Foundation for Post-doctoral Scientists of China (Nos. 20100480857, 201104402).

In order to find novel lead compounds with promising antitumor activity, a series of novel 1, 4-bispiperazine-carbodithioic acid [1-substituted-(1, 2, 3-triazole)-4]-methyl esters were designed and synthesized. Commercially available pi-perazine reacting with CS2 and propargyl bromide in the presence of Na3PO4·12H2O in one pot gave compound 1, which was further reacted with appropriately substituted azide derivatives by click reaction to afford desired target compounds 3a3o. The structures were characterized by 1H NMR, 13C NMR and HRMS. The compounds were evaluated for antitumor activity against four selected human tumor cell lines of EC-9706, MGC-803, SMMC-7721 and MCF-7. Several compounds exhibited moderate to potent activity. Particularly, compound 3a was more potent than 5-fluorouracil against MGC-803 and SMMC-7721 with IC50 values of 11.15 and 14.75 μmol/L.

Key words: 1,2,3-triazole, dithiocarbamate, click chemistry, antitumor activity