Molecular modeling of cytotoxic activity of a new terpenoid-like bischalcone

Abstract

This study describes the synthesis and structure of (1E,4E)-1-(3-chlorophenyl)-5-(2,6,6-trimethylcyclohex-1-en-1-yl)penta-1,4-dien-3-one (BC I). X-ray single-crystal diffraction and Hirshfeld surface analysis describe supramolecular arrangement and topological analysis. Theoretical calculations, such as QTAIM, frontier molecular orbital, MEP and infrared spectra assignments, were performed at the B3LYP/6-311++G(d,p) level of theory. Also, this work evaluates molecular docking against DNA (PDB ID: 1BNA) and cytotoxic activity against two tumor cell lines. The BC I molecule has a half chair conformation of the cyclohexene ring, and the supramolecular arrangements are stabilized by C₆–H₆⋯O₁ and C₇–H₇⋯O₁ interactions. MEP and docking analyses indicate an electrophilic attack that is likely to occur on the carbonyl group.