Design, Synthesis, Biological Activity and Molecular Docking Study of Coumarin Derivatives Bearing 2-Methyl b iphenyl Moiety

doi:10.1007/s40242-019-8310-7

Chemical Research in Chinese Universities ›› 2019, Vol. 35 ›› Issue (3): 410-417.doi: 10.1007/s40242-019-8310-7

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Design, Synthesis, Biological Activity and Molecular Docking Study of Coumarin Derivatives Bearing 2-Methyl b iphenyl Moiety

MA Junjie¹, HUANG Kun¹, NI Xin¹, CHEN Roufen¹, XU Boxuan², WANG Cuifang³

1. School of Medicine, Huaqiao University, Quanzhou 362000, P. R. China;
2. Key Laboratory of Structure-based Drug Design and Discovery, Ministry of Education, Shenyang Pharmaceutical University, Shenyang 110016, P. R. China;
3. College of Oceanology and Food Science, Quanzhou Normal University, Quanzhou 362000, P. R. China

Received:2018-09-25 Revised:2019-02-28 Online:2019-06-01 Published:2019-03-27
Contact: MA Junjie, WANG Cuifang E-mail:majunjie3612@hqu.edu.cn;wlycf@163.com
Supported by:
Supported by the National Natural Science Foundation of China(No.81602970), the Promotion Program for Young and Mid-dle-aged Teacher in Science and Technology Research of Huaqiao University, China(No.ZQN-PY519), the Science and Techno- logy Project of Quanzhou City, China(No.2018C074R) and the Subsidized Project for Postgraduates' Innovative Fund in Scientific Research of Huaqiao University, China.

Abstract

Abstract: A hybrid pharmacophore approach was used to design and synthesize a series of coumarin derivatives bearing 2-methylbiphenyl moiety, which were evaluated for their in vitro anticancer activities against four cancer cell lines(MCF-7, A549, H460 and HT29) and PD-1/PD-L1 inhibitory activities. Moreover, several compounds with excellent anticancer activities were selected to evaluate the cytotoxicities against one normal cell line(HEK-293). The most promising compound 11o showed the best anticancer activities against the four tested cancer cell lines with the IC₅₀ values of 6.45, 8.65, 6,57 and 8.13 μmol/L, respectively, and displayed weak cytotoxicity on the normal cell(HEK-293). Furthermore, screening of PD-1/PD-L1inhibitory activity revealed that compound 11o could effectively inhibit the binding of PD-1/PD-L1, and the binding interactions of compound 11o with PD-L1 protein were explored by molecular docking. All above evidences showed that compound 11o might be worthy of further study as a valuable leading compound for the treatment of cancer.

Key words: Coumarin, 2-Methylbiphenyl, Anticancer activity, PD-1/PD-L1 inhibitory activity, Molecular docking

MA Junjie, HUANG Kun, NI Xin, CHEN Roufen, XU Boxuan, WANG Cuifang. Design, Synthesis, Biological Activity and Molecular Docking Study of Coumarin Derivatives Bearing 2-Methyl b iphenyl Moiety[J]. Chemical Research in Chinese Universities, 2019, 35(3): 410-417.

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Design, Synthesis, Biological Activity and Molecular Docking Study of Coumarin Derivatives Bearing 2-Methyl b iphenyl Moiety

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