Novel fluorinated thiazolidin-4-one derivatives: synthesis and anti-cancer potential against HepG2 and HCT116 cell lines

Abstract

A novel synthetic route has been designed to introduce fluorine functionality into a series of compounds containing thiazolidin-4-one rings. These compounds were synthesised from various aniline derivatives using a two-step approach: an addition reaction of ethyl isothiocyanate with different aromatic fluorinated anilines, followed by cyclisation to yield the final products. A total of 15 novel fluorinated thiazolidinone compounds were synthesised and characterised using ¹H NMR, ¹⁹F NMR, Fourier transform–infrared, elemental analysis and liquid chromatography–mass spectrometry. Stereochemistry around the imine bond in the synthesised derivatives was determined using nuclear Overhauser effect spectroscopy. The in vitro anticancer potential of the compounds was tested against two human cancer cell lines, liver (HepG2) and colon (HCT116). The study revealed that the derivatives having fluorine functionality at both the m-positions in the aromatic ring showed promising anticancer potential, as compared to those at o- and p-positions.