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

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 calculated at 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 for cyclohexene ring, and the supramolecular arrangements are stabilized for 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.