Synthesis and biological testing of 3,5-bis(arylidene)-4-piperidone conjugates with
Margarita E Neganova1, Yulia R Aleksandrova1, Natalia S Nikolaeva2
1Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, Moscow 119991, Russia; Institute of Physiologically Active Compounds, Russian Academy of Sciences, Chernogolovka 142432, Russia.
Abstract:
Using the methodology of "click" chemistry, a series of conjugates of 3,5-bis(benzylidene)-1-(prop-2-yn)piperidin-4-ones with 4-alkyl-3-azidomethyl-2-ethoxy-2,5-dihydro-5H-1,2 oxaphosphol 2-oxides was synthesized. All newly obtained compounds 8-18 were characterized by 1H, 13C, 31P, 19F NMR and IR spectroscopy. The potential antitumor activity of the synthesized conjugates8-18was studied in terms of their ability to influence the viability of variouscancercell lines, including A549, SH-SY5Y, Hep-2, and HeLa. Compound 15, which contains two fluorine atoms in the benzene ring, was shown to be the most promising. The mechanism of the cytotoxic action of this conjugate is supposed to be associated with the ability to inhibit the glycolytic profile of transformed cells.
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