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Synthesis of novel oleanolic acid and ursolic acid in C-28 position derivatives as potential anticancer agents

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Abstract

A series of nitrogen-containing derivatives of oleanolic acid and ursolic acid were prepared by a modification at C-28 position via esterification with 2-hydroxyacetic acid followed by amidation with amines, such as piperazine, N-methylpiperazine, and alkane-1, 2-diamines, alkane-1, 4-diamines, alkane-1, 6-diamines. In vitro antiproliferative activities of the compounds prepared towards MCF-7, Hela and A549 cell lines were evaluated by a MTT method to show that OA-5a, OA-5b, OA-5c and UA-5a showed somewhat improved antiproliferative activities against MCF-7, Hela and A549 cells comparing to that of the positive control, gefitinib.

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Acknowledgements

This work was supported by the National Natural Science Foundation of China (Nos. 21102067).

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Authors and Affiliations

  1. School of Chemistry and Chemical Engineering, Liaoning Normal University, Dalian, 116-029, Liaoning, People’s Republic of China

    Tian Tian, Xinyu Liu, Jingyang Sun, Zhonghua Feng & Longxuan Zhao

  2. Liaoning Provincial Key Laboratory of Biotechnology and Drug Discovery, Liaoning Normal University, Dalian, 116-029, Liaoning, People’s Republic of China

    Longxuan Zhao & Chunhui Zhao

  3. College of Pharmacy, Yeungnam University, Kyongsan, 712-749, Korea

    Eung-Seok Lee

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  1. Tian Tian
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  2. Xinyu Liu
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  3. Eung-Seok Lee
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  4. Jingyang Sun
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  5. Zhonghua Feng
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  6. Longxuan Zhao
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  7. Chunhui Zhao
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Correspondence to Longxuan Zhao or Chunhui Zhao.

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Tian, T., Liu, X., Lee, ES. et al. Synthesis of novel oleanolic acid and ursolic acid in C-28 position derivatives as potential anticancer agents. Arch. Pharm. Res. 40, 458–468 (2017). https://doi.org/10.1007/s12272-016-0868-8

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  • DOI: https://doi.org/10.1007/s12272-016-0868-8

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