Synthesis Cytotoxic Effect and DFT Investigation of some Benzoyl Thiourea Compounds

Abstract

Benzoyl thiourea derivatives have garnered significant interest due to their diverse biological and pharmacological properties. A series of benzoyl thiourea derivatives (L1–L5) were synthesized using 4-nitrobenzoyl chloride and 4-methoxybenzoyl chloride as starting acylating agents, reacting with various amines, including 3,4-dimethylaniline, benzene-1,2-diamine, and ethane-1,2-diamine. The chemical structures of the synthesized compounds were confirmed through various spectroscopic techniques, including electron ionization mass spectrometry (EI-MS), Fourier-transform infrared spectroscopy (FT-IR), ^1H and ^13C nuclear magnetic resonance (NMR) spectroscopy, as well as melting point analysis. To support and rationalize the experimental findings, a comprehensive theoretical investigation was performed using Density Functional Theory (DFT) with the B3LYP functional and 6-31G++(d,p) basis set. The computational study involved the determination of frontier molecular orbital energies (HOMO and LUMO), Mulliken atomic charges, and selected structural parameters. Furthermore, the analysis identified key donor atoms in each molecule, providing insights into their electronic behavior. The in vitro cytotoxic potential of the synthesized compounds (L1–L5) was assessed against MCF-7 human breast cancer cell lines using the MTT assay. The results revealed that the compounds exhibited low cytotoxic efficacy under the tested conditions.