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1,5-Diaryl-3-oxo-1,4-pentadienes based on (4-oxopiperidin-1-yl)(aryl)methyl phosphonate scaffold: synthesis and antitumor properties

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Abstract

Novel 3,5-bis(arylidene)-4-piperidones modified with diethyl[(aryl)methyl]phosphonate moiety attached to the piperidone nitrogen atom have been synthesized by crotonic condensation of aromatic aldehydes with diethyl[(4-oxopiperidin-1-yl)(aryl)methyl]phosphonates in the presence of LiClO4/Et3N system or acetonitrile solution of boron trifluoride etherate. The synthesized phosphonate derivatives of 3,5-bis(arylidene)-4-piperidone series displayed inhibitory properties toward RD, PC3, HCT116, and MCF7 human cancer cell lines with IC50 values in the range of 2.5–8.5 μM, as assessed by an in vitro 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide assay.

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Acknowledgments

This work was supported by the Russian Foundation for Basic Research (project no. 14-03-00687).

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Authors and Affiliations

  1. Nesmeyanov Institute of Organoelement Compounds, RAS, Moscow, 119991, Russian Federation

    Mikhail V. Makarov, Victor N. Khrustalev, Zinaida S. Klemenkova & Valery K. Brel

  2. Institute of Carcinogenesis, Blokhin Russian Cancer Research Center, Moscow, 115478, Russian Federation

    Ekaterina Yu. Rybalkina

  3. Institute of Physiologically Active Substances, RAS, Chernogolovka, 142432, Russian Federation

    Lada V. Anikina, Sergey A. Pukhov, Sergey G. Klochkov & Margarita E. Neganova

  4. Institute of Problems of Chemical Physics, RAS, Chernogolovka, 142432, Russian Federation

    Denis V. Mischenko

  5. Peoples’ Friendship University of Russia, Moscow, 117198, Russian Federation

    Victor N. Khrustalev

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  1. Mikhail V. Makarov
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  2. Ekaterina Yu. Rybalkina
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  3. Lada V. Anikina
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  9. Zinaida S. Klemenkova
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Correspondence to Mikhail V. Makarov.

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Makarov, M.V., Rybalkina, E.Y., Anikina, L.V. et al. 1,5-Diaryl-3-oxo-1,4-pentadienes based on (4-oxopiperidin-1-yl)(aryl)methyl phosphonate scaffold: synthesis and antitumor properties. Med Chem Res 26, 140–152 (2017). https://doi.org/10.1007/s00044-016-1726-4

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  • DOI: https://doi.org/10.1007/s00044-016-1726-4

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