Research Information System
Journal of Molecular Structure, vol.1355, 2026 (SCI-Expanded, Scopus)
A new 1,2,3-triazole-based compound, 1-(4-((1-(3,4-dichlorophenyl)-1H-1,2,3-triazol-4-yl)methoxy)-2-hydroxyphenyl)ethan-1-one, was synthesized via click chemistry and characterized using FT-IR, NMR, MALDI-TOF-MS, elemental analysis and single-crystal X-ray diffraction (SCXRD). Crystallographic analysis revealed an orthorhombic system with space group Pbca and void volume of 294.34 Å3, indicating efficient molecular packing. Hirshfeld surface and energy framework analyses showed that dispersion interactions and hydrogen bonding dominate the crystal stabilization. Molecular docking analyses revealed strong multi-target affinity, including minor-groove binding to DNA (PDB 1BNA), interaction with IMPDH2 (PDB 6UAJ) and binding to the active site of CA12 (PDB 1JCZ). These interactions suggest that the compound can simultaneously interfere with DNA replication, guanine nucleotide synthesis and carbonic-anhydrase-mediated redox regulation. In vitro cytotoxicity assays (MTT) demonstrated that the compound exhibited stronger anticancer activity than etoposide across multiple human cancer cell lines, showing the most potent effect in MDA-MB-231 cells (IC50=14.85±0.11 µM at 48 h). A high selectivity index (SI = 5.65) indicated preferential activity toward cancer cells. Annexin V/7-AAD staining confirmed dose-dependent apoptosis, supported by mitochondrial membrane potential (MMP) loss and increased reactive oxygen species (ROS) levels, indicating apoptosis induction through oxidative stress pathways. These results indicating potential of this triazole derivative as a selective and potent anticancer agent.