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

doi:10.6023/cjoc201610044

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

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4-(甲氧基噻吩基)-3-(取代苯甲酰基)-吡咯类化合物的合成与抗肿瘤活性研究

赵凯, 王帅, 詹晓平, 刘增路, 毛振民

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 E-mail:zmmao@sjtu.edu.cn
基金资助:
国家科技重大新药创制专项（No.2010ZX09401404-004）资助项目.

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

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

School of Pharmacy, Shanghai JiaoTong University, Shanghai, 200240

Received:2016-10-28 Revised:2016-12-02 Published:2017-01-04
Contact: 10.6023/cjoc201610044 E-mail:zmmao@sjtu.edu.cn
Supported by:
Project supported by the National Science and Technology Major Special Drug Discovery (No. 2010ZX09401404-004).

1. Synthesis and Anti-tumor Activity of 4-(Methoxyl thienyl)-3- (substituted benzoyl)pyrroles.PDF(3431KB)

Abstract

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

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Zhao Kai, Wang Shuai, Zhan Xiaoping, Liu Zenglu, Mao Zhenmin. Synthesis and Anti-tumor Activity of 4-(Methoxyl thienyl)-3- (substituted benzoyl)pyrroles[J]. Chin. J. Org. Chem., 2017, 37(4): 943-953.

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4-(甲氧基噻吩基)-3-(取代苯甲酰基)-吡咯类化合物的合成与抗肿瘤活性研究

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

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