Molecular structure and biological activities of 4-thiazolidinone derivatives: a combined theoretical and experimental study

In this study, we report the structural and biological characterization of (2Z,5Z)-5-(4-methyl benzylidene)-3-(2-methylpropyl)-2-(phenylimino)-1,3-thiazolin-4-one (6a) and (2Z,5Z)-5-(3-chlorobenzylidene)-3-(2-methylpropyl)-2-(phenylimino)-1,3-thiazolin-4-one (6b). These compounds were synthesized following the reported method and the molecular structures were confirmed by single-crystal X-ray diffraction studies. Density functional theory (DFT) calculation was carried out to complement the structural and spectral features. In vitro cytotoxicity of the compounds was tested against both the cancerous (SW-480 & MCF-7) and normal (HEK-293) cell lines using the MTT assay. The results indicated that compounds adopted (Z,Z)-configuration with respect to the exocyclic methylene proton and the exocyclic nitrogen. It was observed that compound 6a (IC50 = 190 +/- 0.23 mu g/mL on SW-480 & IC50 = 330 +/- 0.27 mu g/mL on MCF-7) showed a weaker anti-proliferative effect than 6b (IC50 = 119.87 +/- 0.24 mu g/mL on SW-480 & IC50 = 140.39 +/- 0.28 mu g/mL on MCF-7). These compounds showed acceptable toxicity on normal cell line.

Automated summary

This study reports the structural and biological characterization of two new compounds and evaluates their cytotoxicity against cancerous and normal cell lines. The results indicate that one of the compounds shows weaker anti-proliferative effect, but they both exhibit acceptable toxicity on normal cells.