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Design and synthesis of 1,4-dihydropyridine and cinnamic acid esters and their antioxidant properties

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Abstract

In this study, cinnamic acid derivatives with pyridine ring were synthesized via Hantzsch reaction in order to expand conjugation system and their antioxidant abilities were tested. According to the evaluation results of their antioxidant properties, compounds 2 and 3 have similar antioxidant activity to prevent DNA from •OH– and Cu2+/GSH induced oxidation, demonstrating that 1,4-dihydropyridine and pyridine nucleus exhibit good resistance to oxidation while the substituents have little effect. In the meantime, the AAPH-induced oxidative DNA damage [AAPH=2,2′-azobis(2-methylpropionamidine)dihydrochloride] and trapping ABTS+• test show that N—H bond and large conjugation systems are the pivotal parts to improve the activities of antioxidant.

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Authors and Affiliations

  1. School of Stomatology, Capital Medical University, Beijing, 100050, P. R. China

    Yang Gao & Zheng Sun

  2. The Second Hospital of Jilin University, Changchun, 130021, P. R. China

    Bowei Wang

  3. School of Stomatology, Jilin University, Changchun, 130021, P. R. China

    Shang Gao, Ruhui Zhang, Chunying Yang & Zhihui Liu

Authors
  1. Yang Gao
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  2. Bowei Wang
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  3. Shang Gao
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  4. Ruhui Zhang
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  5. Chunying Yang
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  6. Zheng Sun
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  7. Zhihui Liu
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Corresponding authors

Correspondence to Zheng Sun or Zhihui Liu.

Additional information

Supported by the Special Pharmaceutical Fund of Jilin Province, China(Nos.20140311088YY, 20150311070YY).

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Gao, Y., Wang, B., Gao, S. et al. Design and synthesis of 1,4-dihydropyridine and cinnamic acid esters and their antioxidant properties. Chem. Res. Chin. Univ. 32, 594–599 (2016). https://doi.org/10.1007/s40242-016-6047-0

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  • DOI: https://doi.org/10.1007/s40242-016-6047-0

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