Synthesis and bioactivity of 2-cyanoacrylates containing a trifluoromethylphenyl moiety

A series of 2-cyanoacrylates containing a trifluoromethylphenyl moiety were synthesized in three steps: ethyl 2-cyano-3,3-dimethylthioacrylate was prepared from ethyl cyanoacetate with carbon disulfide and dimethyl sulfate, then its reaction with 4-trifluoromethylaniline yielded ethyl 2-cyano-3-(4-trifluoromethylphenylamino)-3-methylthioacrylate, and then reacted with an alkylamine. The new structures were verified by elemental analysis, IR, H-1 NMR and mass spectra. In the MTT test, these new compounds were found to possess high antitumor activities against PC3 and A431 cells. (C) 2004 Elsevier B.V. All rights reserved.