Asymmetric synthesis of phenanthroindolizidine alkaloids with hydroxyl group at the C14 position and evaluation of their antitumor activities

https://doi.org/10.1016/j.bmcl.2010.11.008Get rights and content

Abstract

The asymmetric total synthesis of the strongly cytotoxic phenanthroindolizidine alkaloid 3 was achieved. Using the same route, various derivatives were also synthesized. Cytotoxicity of those synthetic compounds was evaluated and compounds 19, 23, and 27 demonstrated potent cytotoxicities similar to that of 3. The in vivo antitumor efficacy of selected compounds was also evaluated and 23 demonstrated moderate antitumor efficacy.

Graphical abstract

The asymmetric total synthesis of the strongly cytotoxic phenanthroindolizidine alkaloid 3 was achieved. Using the same route, various derivatives were also synthesized. Cytotoxicity of those synthetic compounds and the in vivo antitumor efficacy of selected compounds were evaluated.

  1. Download : Download high-res image (36KB)
  2. Download : Download full-size image

Section snippets

Acknowledgments

The authors thank Miyuki Uchida and Fukiko Nishisaka for their excellent technical assistance.

References and notes (16)

  • B. Baumgartner et al.

    Phytochemistry

    (1990)
  • W. Gao et al.

    Bioorg. Med. Chem. Lett.

    (2008)
  • W. Gao et al.

    Bioorg. Med. Chem. Lett.

    (2007)
  • X. You et al.

    Arthritis Rheum.

    (2006)
  • C.-W. Yang et al.

    Mol. Pharmacol.

    (2006)
  • W. Gao et al.

    Cancer Res.

    (2004)
  • E. Gellert

    Alkaloids: Chemical and Biological Perspectives

  • H. Komatsu et al.

    J. Med. Chem.

    (2001)
There are more references available in the full text version of this article.

Cited by (0)

View full text