Skip to main content
SpringerLink
Log in

Synthesis and Biological Evaluation of Ligustrazine Derivatives

  • Published:
Chemistry of Natural Compounds Aims and scope

Synthesized ligustrazine derivatives (1a, 1b, 1c (novel)) were structurally confirmed by mass spectrometry, 1H NMR, and 13C NMR. The cytotoxic activities of all derivatives were evaluated by MTS assay in three human prostate cancer cell lines (PC-3, LNCaP, and DU145) and in the A549 human lung cancer cell line. Compound 1a exhibited strong cytotoxic activity against PC-3 cells (IC50 3.63 μM). In addition, compounds 1–1c showed moderate α 1-adrenergic receptor (AR) subselective antagonistic and β 2-AR agonistic effects, indicating potential use for the treatment of chronic obstructive pulmonary disease. Molecular docking results showed 1b bound to one region of the active site in β 2-AR, but 1, 1a, and 1c bound to a different region.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

References

  1. X. C. Cheng, X. Y. Liu, W. F. Xu, X. L. Guo, and Y. Ou, Bioorg. Med. Chem., 15, 3315 (2007).

    Article  CAS  PubMed  Google Scholar 

  2. C. C. Tsai, T. Y. Lai, W. C. Huang, I. M. Liu, and J. T. Cheng, Life Sci., 71, 1321 (2002).

    Article  CAS  PubMed  Google Scholar 

  3. X. L. Zhu, L. Z. Xiong, Q. Wang, Z. G. Liu, X. Ma, Z. H. Zhu, S. Hu, G. Gong, and S. Y. Chen, Neurosci Lett., 449, 24 (2009).

    Article  CAS  PubMed  Google Scholar 

  4. D. H. Wu, X. J. Xu, M. Z. Zhang, and L. Wang, Lett. Drug Des. Discov., 8, 1009 (2011).

    Article  CAS  Google Scholar 

  5. R. Barbaro, L. Betti, M. Botta, F. Corelli, G. Giannaccini, L. Maccari, F. Manetti, G. Strappaghetti, and F. Corsano, J. Med. Chem., 44, 2118 (2001).

    Article  CAS  PubMed  Google Scholar 

  6. S. C. Sato, T. Hatanaka, H.Yuyama, M. Ukai, Y. Noguchi, A. Ohtake, K. Taguchi, M. Sasamata, and K. Miyata, Biol. Pharm. Bull., 35, 72 (2012).

  7. Sybyl Molecular Modeling Software Packages, V 8.1.1, TRIPOS Inc., St Louis, 2009.

  8. V. Cherezov, D. M. Rosenbaum, M. A. Hanson, S. G. Rasmussen, F. S. Thian, T. S. Kobilka, H. J. Choi, P. Kuhn, W. I. Weis, B. K. Kobilka, and R. C. Stevens, Science, 318, 1258 (2007).

    Article  CAS  PubMed  PubMed Central  Google Scholar 

Download references

Acknowledgment

This work was supported by the Department of Education of Guangdong Province scientific research projects fund (Nos. 2013KJCX0151 and 2014KTSCX096).

Author information

Authors and Affiliations

  1. School of Pharmaceutical Sciences, Guangzhou Medical University, Xinzao, Panyu District, 511436, Guangzhou, People’s Republic of China

    Chao Zhang, Lang-di Chen, Xin-tong Liang, Wei-xiong Liu & Wen-hao Wu

Authors
  1. Chao Zhang
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Lang-di Chen
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Xin-tong Liang
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Wei-xiong Liu
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Wen-hao Wu
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Chao Zhang.

Additional information

Published in Khimiya Prirodnykh Soedinenii, No. 1, January–February, 2017, pp. 96–98.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Zhang, C., Chen, Ld., Liang, Xt. et al. Synthesis and Biological Evaluation of Ligustrazine Derivatives. Chem Nat Compd 53, 114–117 (2017). https://doi.org/10.1007/s10600-017-1922-6

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10600-017-1922-6

Keywords

Search

Navigation