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Russian Journal of Organic Chemistry

, Volume 54, Issue 10, pp 1480–1485 | Cite as

3,28-Bis-O-polyfluorobenzoylbetulin. Synthesis, Molecular Structure, and Cytotoxicity

  • Yu. G. TrishinEmail author
  • A. N. Fedorov
  • K. A. Lyssenko
  • D. S. Prokof’eva
  • Yu. S. Rudenok
  • V. V. Pavlova
Article
  • 14 Downloads

Abstract

Treatment of betulin with 2,3,4,5-tetrafluoro- and pentafluorobenzoyl chlorides in triethylamine afforded 3,28-bis-O-polyfluorobenzoylbetulins. According to the X-ray diffraction data, all six-membered rings in the 3,28-bis-O-pentafluorobenzoylbetulin molecule appear in a chair conformation, and the five-membered ring has an envelope conformation with the C17 atom deviating from the plane formed by the other four carbon atoms. Unlike betulin itself, the obtained bis-esters showed no cytotoxic effect on human lung adenocarcinoma cell line A549 and human glioblastoma cell line U251.

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Copyright information

© Pleiades Publishing, Ltd. 2018

Authors and Affiliations

  • Yu. G. Trishin
    • 1
    Email author
  • A. N. Fedorov
    • 1
  • K. A. Lyssenko
    • 2
  • D. S. Prokof’eva
    • 3
  • Yu. S. Rudenok
    • 1
  • V. V. Pavlova
    • 1
  1. 1.Higher School of Technology and EnergySt. Petersburg State University of Industrial Technologies and DesignSt. PetersburgRussia
  2. 2.Nesmeyanov Institute of Organoelement CompoundsRussian Academy of SciencesMoscowRussia
  3. 3.Institute of Experimental PharmacologyKuz’molovskii, Leningrad oblastRussia

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