Synthesis and Anti-tumor Activity of Novel 3-Substituted-benzoyl-4-substituted-thienyl-pyrroles

doi:10.6023/cjoc201510016

Chin. J. Org. Chem. ›› 2016, Vol. 36 ›› Issue (3): 572-579.DOI: 10.6023/cjoc201510016 Previous Articles Next Articles

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新型3-取代苯甲酰基-4-取代噻吩基吡咯类化合物的合成及抗肿瘤活性研究

陈简, 张袁魁, 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:2015-10-14 修回日期:2015-11-06 发布日期:2015-11-20
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 Novel 3-Substituted-benzoyl-4-substituted-thienyl-pyrroles

Chen Jian, Zhang Yuankui, Zhan Xiaoping, Liu Zenglu, Mao Zhenmin

School of Pharmacy, Shanghai Jiao Tong University, Shanghai 200240

Received:2015-10-14 Revised:2015-11-06 Published:2015-11-20
Supported by:
Project supported by the National Science and Technology Major Special Drug Discovery (No. 2010ZX09401404-004).

1. Synthesis and Anti-tumor Activity of Novel 3-Substituted-benzoyl-4-substituted-thienyl-pyrroles.PDF(4345KB)

Abstract

29 novel 3-substituted-benzoyl-4-substituted-thienyl-pyrrole compounds 2a~5c were synthesized via aldol condensation and Van Leusen pyrrole reaction using substituted acetophenone and substituted 2-thenaldehyde as raw materials, and the cell proliferation inhibition efficacy of 2a~5c against human colon cancer (HCT-116), human gastric adenocarcinoma (SGC-7901), human cervical carcinoma (Hela) and human umbilical vein endothelial (HUVEC) cell lines were estimated. Then MTT assay was used to evaluate the anti-proliferative activity. The result indicated that some target compounds exhibited strong (IC₅₀≤20 μmol·L^-¹) or moderate (20 μmol·L^-¹50≤50 μmol·L^-¹) proliferation inhibition efficacy against tumor cells, meanwhile didn't have significate inhibition effect on HUVEC. Compounds 2c, 2i, 3i, 3j, 4a~4f and 5c showed strong or moderate inhibition efficacy against HCT-116. The IC₅₀ value of 2j was 4.3 μmol·L^-¹ against Hela, and compounds 2i and 3j exhibited moderate inhibition efficacy against Hela. The IC₅₀ value of 3j was 10.5 μmol·L^-¹ against SGC-7901, and compounds 2i indicated moderate inhibition efficacy against SGC-7901. Compounds 2i and 3j showed broad anti-proliferative activity against all selected tumor cells.

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

Cite this article

Chen Jian, Zhang Yuankui, Zhan Xiaoping, Liu Zenglu, Mao Zhenmin. Synthesis and Anti-tumor Activity of Novel 3-Substituted-benzoyl-4-substituted-thienyl-pyrroles[J]. Chin. J. Org. Chem., 2016, 36(3): 572-579.

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新型3-取代苯甲酰基-4-取代噻吩基吡咯类化合物的合成及抗肿瘤活性研究

Synthesis and Anti-tumor Activity of Novel 3-Substituted-benzoyl-4-substituted-thienyl-pyrroles

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