Chin. J. Org. Chem. ›› 2018, Vol. 38 ›› Issue (5): 1242-1250.DOI: 10.6023/cjoc201709022 Previous Articles     Next Articles



李英俊a, 王思远a, 靳焜b, 高立信c, 盛丽c, 张楠a, 杨凯栋a, 赵月a, 李佳c   

  1. a 辽宁师范大学化学化工学院 大连 116029;
    b 大连理工大学精细化工国家重点实验室 大连 116012;
    c 中国科学院上海药物研究所 国家新药筛选中心 药物研究国家重点实验室 上海 201203
  • 收稿日期:2017-09-13 修回日期:2017-12-04 发布日期:2018-01-03
  • 通讯作者: 李英俊,
  • 基金资助:


Synthesis and Cell Division Cycle 25B Phosphatase/Protein Tyrosine Phosphatase 1B Inhibitory Activity Evaluation of Novel Acylthiourea Derivatives

Li Yingjuna, Wang Siyuana, Jin Kunb, Gao Lixinc, Sheng Lic, Zhang Nana, Yang Kaidonga, Zhao Yuea, Li Jianc   

  1. a College of Chemistry and Chemical Engineering, Liaoning Normal University, Dalian 116029;
    b State Key Laboratory of Fine Chemicals, Dalian University of Technology, Dalian 116012;
    c State Key Laboratory of Drug Research, National Center for Drug Screening, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Shanghai 201203
  • Received:2017-09-13 Revised:2017-12-04 Published:2018-01-03
  • Contact: 10.6023/cjoc201709022
  • Supported by:

    Project supported by the Natural Science Foundation of Liaoning Province (No. 20102126).

A series of new acylthiourea derivatives 3 containing carbazole moity have been synthesized by the techniques of ultrasonic irradiation and solid-liquid phase transfer catalysis. Their structures were characterized by IR, 1H NMR, 13C NMR spectra and elemental analysis. This synthetic method has the advantages of short reaction time, simple operation and high yield. All synthesized target compounds were screened for their inhibitory activity against cell division cycle 25B phosphatase (Cdc25B) and protein tyrosine phosphatase 1B (PTP1B). The results show that all the compounds 3 display significant inhibitory activities against Cdc25B, and partial target compounds 3 also show significant inhibitory activities against PTP1B. Among them, 1-(4-nitrobenzoyl)-3-(9-ethyl-carbazole-3-yl)thiourea (3n) exhibits highest inhibitory activity against Cdc25B [IC50=(0.49±0.12) mg/mL] and 1-(2-nitrobenzoyl)-3-(9-ethyl-carbazole-3-yl)thiourea (3l) displays highest inhibitory activity against PTP1B [IC50=(3.59±1.15) mg/mL]. It is noteworthy that compound 3n shows higher inhibitory activity against Cdc25B and PTP1B. The preliminary research results of molecular docking revealed the structural-activity of the inhibitors. The active compounds can be considered as potential Cdc25B and PTP1B inhibitors, and have great application prospects in the treatment of cancers and diabetes.

Key words: acylthiourea, carbazole, synthesis, Cdc25B and PTP1B inhibitors, molecular docking