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

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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.

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Authors and Affiliations

  1. Arbuzov Institute of Organic and Physical Chemistry, Kazan Scientific Center, Russian Academy of Sciences, ul. Akademika Arbuzova 8, 420088, Kazan, Tatarstan, Russia

    I. Yu. Strobykina, A. V. Nemtarev, B. F. Garifullin, A. D. Voloshina, A. S. Sapunova & V. E. Kataev

Authors
  1. I. Yu. Strobykina
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  2. A. V. Nemtarev
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  3. B. F. Garifullin
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  4. A. D. Voloshina
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  5. A. S. Sapunova
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  6. V. E. Kataev
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Correspondence to V. E. Kataev.

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Dedicated to Full Member of the Russian Academy of Sciences A.I. Konovalov on his 85th anniversary

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Strobykina, I.Y., Nemtarev, A.V., Garifullin, B.F. et al. Synthesis and Biological Activity of Alkane-1,1-diylbis(phosphonates) of Diterpenoid Isosteviol. Russ J Org Chem 55, 17–24 (2019). https://doi.org/10.1134/S1070428019010044

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  • DOI: https://doi.org/10.1134/S1070428019010044

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