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Synthesis and biological evaluation of hydroxylcoumarin derivatives as antioxidant agents

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Abstract

In this study, esculetin(1) was chosen as a lead compound and some structural modifications were designed to explore the antioxidant activities of esculetin derivatives. Meanwhile, a convenient method for selective methylation of catechol coumarins with different bases was developed. Furthermore, a few 5,7-dihydroxylcoumarins were synthesized and 7-hydroxylcoumarins were employed in order to explore the potential structure-antioxidant activity relationships. The antioxidant activities of these compounds were evaluated and compared with standard antioxidant Trolox by the 2,2′-diphenyl-1-picrylhydrazyl(DPPH) assay, 2,2′-azinobis-(3-ethylbenzthiazoline-6-sulfonate) cation(ABTS+) assay and ferric reducing antioxidant power(FRAP) assay. The results show that the catechol group is the key pharmacophore. Meanwhile, introducing electronegative groups at the C4 position of esculetin(1) may enhance the antioxidative capacity, while introducing a group containing nitrogen as a hydrogen bond acceptor at the C8 position may slightly reduce the antioxidative capacity. Among them, the most powerful antioxidants are com-pounds 5 and 7, which exhibit higher antioxidant activity than esculetin(1) in all assays.

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Authors and Affiliations

  1. College of Life Science, Dalian Minzu University, Dalian, 116600, P. R. China

    Chen Chen & Wenzhong Hu

  2. Laboratory of Pharmaceutical Resource Discovery, Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian, 116023, P. R. China

    Ping Wang, Liwei Zou, Ling Yang, Yiming Fan & Guangbo Ge

Authors
  1. Chen Chen
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  2. Ping Wang
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  3. Liwei Zou
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  4. Ling Yang
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  5. Yiming Fan
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  6. Wenzhong Hu
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  7. Guangbo Ge
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Corresponding authors

Correspondence to Ping Wang or Guangbo Ge.

Additional information

Supported by the National Basic Research Program of China(No.2013CB531800), the National Natural Science Foundation of China(Nos.81402822, 81603187, 31471923, 31601517) and the Fundamental Research Funds for the Central Universities of China(No.DC201501020101).

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Chen, C., Wang, P., Zou, L. et al. Synthesis and biological evaluation of hydroxylcoumarin derivatives as antioxidant agents. Chem. Res. Chin. Univ. 33, 194–199 (2017). https://doi.org/10.1007/s40242-017-6411-8

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  • DOI: https://doi.org/10.1007/s40242-017-6411-8

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