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Chemistry of Natural Compounds

, Volume 55, Issue 5, pp 883–889 | Cite as

Synthesis and Cytotoxicity of A-Azepanodammaradiene

  • I. E. SmirnovaEmail author
  • A. V. Petrova
  • O. B. Kazakova
Article
  • 28 Downloads

Sequential transformations of dipterocarpol (oximation, first-order Beckmann rearrangement, dehydration, isomerization) synthesized the new dammarane-type triterpenoid A-azepanodammara-20(21),24(25)-diene. Its cytotoxicity was studied in vitro against 60 cell lines of 9 human tumor types. The cytotoxicity against all cancer cell types increased significantly as compared to native dipterocarpol if an azepane fragment was introduced into ring A (percent inhibition from 15.72% to 82.08%). Detailed cytotoxicity studies confirmed the activity against a broad spectrum of human tumor cell lines with a mean (MID) log LC50 of 5.57.

Keywords

dammarane triterpenoids dipterocarpol azepanes cytotoxicity 

Notes

Acknowledgment

The work was performed on State Task Topic No. AAAA-A17-117011910023-2. We thank the National Cancer Institute for determining the in vitro antitumor activity of 1 and 35.

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Copyright information

© Springer Science+Business Media, LLC, part of Springer Nature 2019

Authors and Affiliations

  • I. E. Smirnova
    • 1
    Email author
  • A. V. Petrova
    • 1
  • O. B. Kazakova
    • 1
  1. 1.Ufa Institute of Chemistry, Ufa Scientific CenterRussian Academy of SciencesUfaRussia

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