(Thio)substituted-1,4-benzoquinones: Synthesis, electrochemistry, DFT calculations and potential antiproliferative effect against MDAMB- 231 cells

Abstract

This study explores the synthesis, electrochemical properties, and computational aspects of mono-, bis-, tris-, and tetrakis(thio)-substituted 1,4-benzoquinones. The electrochemical properties of the compounds were analyzed using staircase cyclic voltammetry (CV). Ground-state energies were determined through time-dependent density functional theory (TD-DFT), utilizing the B3LYP functional and the 6-311G(d,p) basis set. Additionally, the in vitro anticancer efficacy of 2-(tert-butylthio)-3,5,6-trichloro-cyclohexa-2,5-diene-1,4-dione (compound 5) was evaluated using the triple-negative breast cancer cell line (MDA-MB-231). Notably, compound 5 demonstrated significant potency, with values of 50 µM 50 % cytotoxic concentration (IC50).

Keywords

• Benzoquinones, thiols, p-chloranil, Time Dependent Density Functional Theory