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

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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.

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Authors and Affiliations

  1. School of Medicine, Huaqiao University, Quanzhou, 362000, P. R. China

    Junjie Ma, Kun Huang, Xin Ni & Roufen Chen

  2. Key Laboratory of Structure-based Drug Design and Discovery, Ministry of Education, Shenyang Pharmaceutical University, Shenyang, 110016, P. R. China

    Boxuan Xu

  3. College of Oceanology and Food Science, Quanzhou Normal University, Quanzhou, 362000, P. R. China

    Cuifang Wang

Authors
  1. Junjie Ma
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  2. Kun Huang
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  3. Xin Ni
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  4. Roufen Chen
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  5. Boxuan Xu
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  6. Cuifang Wang
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Corresponding authors

Correspondence to Junjie Ma or Cuifang Wang.

Additional information

Supported by the National Natural Science Foundation of China(No.81602970), the Promotion Program for Young and Middle- aged Teacher in Science and Technology Research of Huaqiao University, China(No.ZQN-PY519), the Science and Technology Project of Quanzhou City, China(No.2018C074R) and the Subsidized Project for Postgraduates’ Innovative Fund in Scientific Research of Huaqiao University, China.

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Ma, J., Huang, K., Ni, X. et al. Design, Synthesis, Biological Activity and Molecular Docking Study of Coumarin Derivatives Bearing 2-Methylbiphenyl Moiety. Chem. Res. Chin. Univ. 35, 410–417 (2019). https://doi.org/10.1007/s40242-019-8310-7

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  • DOI: https://doi.org/10.1007/s40242-019-8310-7

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