Synthesis, characterization and evaluation of in vitro anticancer potential of novel fluorinated 5-benzylidene-3-ethyl-2-(2-methyl-3-trifluoromethyl-phenylimino)thiazolidin-4-one derivatives: Comparison of reflux and ultrasonic conditions for Knoevenagel reaction

A set of novel 5-benzylidene-3-ethyl-2-(2-methyl-3-trifluoromethyl-phenylimino)-thiazolidin-4-one derivatives have been synthesized by Knoevenagel reaction via both conventional as well as non-conventional methods on the synthesized iminothiazolidinone core. In terms of yield and reaction time, the ultrasound mediated Knoevenagel reaction method has proved to be more effective than the conventional approach using heat. The H-1 NMR spectra have been used to deduce the structure of the compounds, while LC-MS, FTIR, and elemental analysis data have also been utilized for better confirmation. Using a 2D NOESY NMR experiment, the stereochemistry of the final compound has been verified. The synthesized benzylidine compounds have been screened for in vitro anticancer potential against Human Hepatoma (Hep-G2) cell line. The compound having p-substituted methoxy group on benzylidine moiety is observed to be the most active against the tested cell line as compared to the rest of the compounds.