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Russian Journal of Organic Chemistry

, Volume 55, Issue 1, pp 17–24 | Cite as

Synthesis and Biological Activity of Alkane-1,1-diylbis(phosphonates) of Diterpenoid Isosteviol

  • I. Yu. Strobykina
  • A. V. Nemtarev
  • B. F. Garifullin
  • A. D. Voloshina
  • A. S. Sapunova
  • V. E. KataevEmail author
Article
  • 4 Downloads

Abstract

Isosteviol reacted with α,ω-dibromoalkanes to give 19-(ω-bromoahkyl) esters which were treated with tetraethyl methylenebis(phosphonate) to obtain bis(phosphonates) conjugated to the deterpenoid skeleton through a polymethylene spacer. The bis(phosphonates) were converted to the corresponding bis(phosphonic acids) by transformation to trimethylsilyl esters and subsequent methanolysis. One of the synthesized compounds showed a high antimicrobial activity (MIC 3.9 µg/mL) against S. aureus and a high cytotoxicity (IC50 15–18 µM) toward M-HeLa and MCF-7 human cancer cell lines.

Keywords

Isosteviol phosphonates phosphonic acids antimicrobial activity cytotoxicity 

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Copyright information

© Pleiades Publishing, Ltd. 2019

Authors and Affiliations

  • I. Yu. Strobykina
    • 1
  • A. V. Nemtarev
    • 1
  • B. F. Garifullin
    • 1
  • A. D. Voloshina
    • 1
  • A. S. Sapunova
    • 1
  • V. E. Kataev
    • 1
    Email author
  1. 1.Arbuzov Institute of Organic and Physical ChemistryKazan Scientific Center, Russian Academy of SciencesKazan, TatarstanRussia

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