2,4-bis(bromomethyl)-1,3,5-trimethylbenzene with 2-mercaptopyridine based derivative: Synthesis, crystal structure, in vitro anticancer activity, DFT, Hirshfeld surface analysis, antioxidant, DNA binding and molecular docking studies

•Single crystal of 2-mercaptopyridine based derivative was obtained by slow evaporation method.•Hirshfeld surface analysis and fingerprint plots were performed to confirm the intermolecular interactions in the crystal structure.•The stability and reactivity of M2MCP were achieved from DFT calculations.•In vitro anticancer studies showed that M2MCP has promising anticancer properties.•M2MCP has good DPPH antioxidant character and DNA binding ability. The compound 2,2′-[(2,4,6-trimethyl-1,3 phenylene)bis(methylenesulfanediyl)]dipyridine (M2MCP) was synthesised by the condensation of 2,4-bis(bromomethyl)-1,3,5-trimethylbenzene with 2-mercaptopyridine. The crystal structure of the title molecule is Triclinic with the space group P-1. Using density functional theory, the optimised geometrical parameters were compared with the experimental values. The HOMO and LUMO levels indicate the compound's stability and reactivity. Hirshfeld surface analysis has been used to study the intermolecular interactions. In vitro antioxidant properties reveal that M2MCP has high DPPH scavenging activity. Furthermore, the compound inhibits the human colon cancer cell line HT-29, human lung adenocarcinoma cell line A549 and human gastric cancer cell line MKN45, indicating that it has promising anticancer properties. As a result of its unique interaction mode with DNA, the title compound may act as a potential anticancer agent. Studies using molecular docking indicated that the title compound may inhibit the mouse Aurora A (PDB:3D15). [Display omitted]