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

Abstract

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