Citation: Zhao Kai, Wang Shuai, Zhan Xiaoping, Liu Zenglu, Mao Zhenmin. Synthesis and Anti-tumor Activity of 4-(Methoxyl thienyl)-3-(substituted benzoyl) pyrroles[J]. Chinese Journal of Organic Chemistry, ;2017, 37(4): 943-953. doi: 10.6023/cjoc201610044 shu

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

School of Pharmacy, Shanghai JiaoTong University, Shanghai, 200240

Corresponding author: Mao Zhenmin, zmmao@sjtu.edu.cn
Received Date: 28 October 2016
Revised Date: 2 December 2016

Fund Project: the National Science and Technology Major Special Drug Discovery 2010ZX09401404-004

Figures(3)

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.
- pyrrole,
- thiophene,
- synthesis,
- anti-tumor activity
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