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

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. © 2016, Springer Science+Business Media New York.

Authors
Makarov M.V.1 , Rybalkina E.Y.2 , Anikina L.V.3 , Pukhov S.A.3 , Klochkov S.G.3 , Mischenko D.V.4 , Neganova M.E.3 , Khrustalev V.N. 1, 5 , Klemenkova Z.S.1 , Brel V.K.1
Journal
Medicinal Chemistry Research
Publisher
Birkhauser Boston
Number of issue
1
Language
English
Pages
140-152
Status
Published
Link
External link
DOI
10.1007/s00044-016-1726-4
Volume
26
Year
2017
Organizations
  • 1 Nesmeyanov Institute of Organoelement Compounds, RAS, Moscow, 119991, Russian Federation
  • 2 Institute of Carcinogenesis, Blokhin Russian Cancer Research Center, Moscow, 115478, Russian Federation
  • 3 Institute of Physiologically Active Substances, RAS, Chernogolovka, 142432, Russian Federation
  • 4 Institute of Problems of Chemical Physics, RAS, Chernogolovka, 142432, Russian Federation
  • 5 Peoples’ Friendship University of Russia, Moscow, 117198, Russian Federation
Keywords
1,5-Diaryl-3-oxo-1,4-pentadienes; 3,5-Bis(arylidene)-4-piperidones; Aminophosphonates; Antitumor activity; Aryl(methyl) phosphonates
Date of creation
19.10.2018
Date of change
19.10.2018
Short link
https://repository.rudn.ru/en/records/article/record/6312/
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