Chin. J. Org. Chem. ›› 2017, Vol. 37 ›› Issue (4): 943-953.DOI: 10.6023/cjoc201610044 Previous Articles     Next Articles



赵凯, 王帅, 詹晓平, 刘增路, 毛振民   

  1. 上海交通大学药学院 上海 200240
  • 收稿日期:2016-10-28 修回日期:2016-12-02 发布日期:2017-01-04
  • 通讯作者: 毛振民
  • 基金资助:


Synthesis and Anti-tumor Activity of 4-(Methoxyl thienyl)-3- (substituted benzoyl)pyrroles

Zhao Kai, Wang Shuai, Zhan Xiaoping, Liu Zenglu, Mao Zhenmin   

  1. School of Pharmacy, Shanghai JiaoTong University, Shanghai, 200240
  • Received:2016-10-28 Revised:2016-12-02 Published:2017-01-04
  • Contact: 10.6023/cjoc201610044
  • Supported by:

    Project supported by the National Science and Technology Major Special Drug Discovery (No. 2010ZX09401404-004).

33 novel 4-substituted thienyl pyrrole compounds were synthesized via replacement, Vilsmeier-Hack, aldol condensation and Van Leusen pyrrole reaction using 2-methoxythiophen, 3-methoxythiophene, 3,4-dibromothiophene and substituted acetophenone as raw materials. The structures of all target compounds were characterized by 1H NMR, 13C NMR and HRMS, meanwhile the cell proliferation inhibition efficacy was estimated against CHO, HCT-116, MGC80-3, SGC-7901 and HUVEC cell lines. The results revealed that some target compounds exhibited strong (IC50≤20 μmol/L) or moderate (20 μmol/L < IC50≤50 μmol/L) proliferation inhibition efficacy against tumor cells, meanwhile no significant inhibition activity on HUVEC, which indicated that these compounds had high selectivity. Herein, some compounds showed strong or moderate inhibition efficacy against MGC80-3. The IC50 values of [4-(3,4-dimethoxythiophen-2-yl)-1H-pyrrol-3-yl](4-phenylphenyl)-methanone (4a-2) and [4-(3,4-dimethoxythiophen-2-yl)-1H-pyrrol-3-yl](3-bromophenyl)methanone (4a-7), were 8.6 and 8.5 μmol/L against MGC80-3, respectively, and the IC50 value of 4a-7 was 20.0 μmol/L against HCT-116. Both compounds 4a-2 and 4a-7 exhibited moderate inhibition efficacy against SGC-7901.

Key words: pyrrole, thiophene, synthesis, anti-tumor activity