Citation: 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]. Chinese Journal of Organic Chemistry, ;2016, 36(3): 572-579. doi: 10.6023/cjoc201510016 shu

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

1.
School of Pharmacy, Shanghai Jiao Tong University, Shanghai 200240

Corresponding author: Mao Zhenmin, zmmao@sjtu.edu.cn
Received Date: 14 October 2015
Revised Date: 6 November 2015

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

Figures(2)

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^-1 < IC₅₀≤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 3jexhibited moderate inhibition efficacy against Hela. The IC₅₀ value of 3j was 10.5 μmol·L^-¹ against SGC-7901, and compounds 2iindicated moderate inhibition efficacy against SGC-7901. Compounds 2iand 3j showed broad anti-proliferative activity against all selected tumor cells.
- pyrrole,
- thiophene,
- synthesis,
- MTT assay,
- anti-tumor activity
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沈阳化工大学材料科学与工程学院沈阳 110142