Synthesis, structural characterization and anticancer activity of 3-(3,5-dinitrobenzoyl)-1H-imidazolidine-2-thione

Abstract

The present study describes the synthesis, characterization and in vitro anticancer potential evaluation of a novel 3-(3,5-dinitrobenzoyl)-1H-imidazolidine-2-thione compound. In the first step, structure analysis of the compound has been elucidated by NMR and FT-IR techniques. Theoretical NMR, FT-IR spectra, HOMO and LUMO orbital energies and MEP analyses have been used to determine the activity of the molecule by Gaussian 09 package program using DFT techniques. Furthermore, docking calculations have been performed for the BRCA2 (PDB Code: 3EU7) active side to foresee the possible mechanism of action of the synthesized compound. In the second step of the study, the synthesized compound has been screened for its potential in vitro anticancer activity against MCF-7 human breast cancer cell line using the cell proliferation (XTT), apoptosis, cell cycle arrest and intracellular ROS production assays. The results of XTT test revealed significant dereases in MCF-7 cell viability with the 24h IC₅₀ value of 7.57 µM. It has been also observed that treatment with the IC₅₀ concentration of the compound can significantly induce apoptosis, intracellular ROS production and
G2/M phase arrest in MCF-7 cells.