Chin. J. Org. Chem. ›› 2015, Vol. 35 ›› Issue (1): 129-136.DOI: 10.6023/cjoc201405020 Previous Articles     Next Articles



李英俊a, 于洋a, 靳焜b, 高立信c, 罗潼川a, 盛丽c, 邵昕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:2014-05-12 修回日期:2014-08-01 发布日期:2014-09-25
  • 通讯作者: 李佳
  • 基金资助:

    辽宁省自然科学基金(No. 20102126)资助项目.

Synthesis and Biological Activities of Novel 2,5-Disubstituted- 1,3,4-thiadiazole Derivatives

Li Yingjuna, Yu Yanga, Jin Kunb, Gao Lixinc, Luo Tongchuana, Sheng Lic, Shao Xina, Li Jiac   

  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 National Center for Drug Screening, State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Shanghai 201203
  • Received:2014-05-12 Revised:2014-08-01 Published:2014-09-25
  • Supported by:

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

Sixteen novel 2,5-disubstituted-1,3,4-thiadiazole derivatives containing benzisoselenazolone moiety 7a7p were synthesized by the reaction of 2-amino-5-substituted-1,3,4-thiadiazoles (2) with ortho-(chloroseleno)benzoyl chloride (6). The structures were characterized by IR, 1H NMR spectra and elemental analysis. Their biological activities were evaluated. The experimental results indicate that some compounds exhibit inhibitory activity against cell division cycle 25B phosphatase (Cdc25B) (IC50=1.67~6.66 mmol·L-1). All the target compounds showed good inhibitory activity against protein tyrosine phosphatase 1B (PTP1B) (IC50=0.73~4.50 mmol·L-1), and some compounds exhibited higher inhibitory activity than positive control oleanolic acid (IC50=1.90 mmol·L-1). Compound 7k displayed antitumor activity in vitro for human colon cancer (HCT-8) cell (IC50=12.54 mmol·L-1). Some compounds showed the medium scavenging ability for hydroxyl radical (HO·) and superoxide anion (O2·-), but no scavenging ability for DPPH·.

Key words: 2,5-disubstituted-1,3,4-thiadiazole, benzisoselenazolone, synthesis, bioactivity