This study involved the synthesis of a new category of tetra-1,2,3-triazole derivatives of types (I), (II), (III), and (IV) 7-14 using a Cu(I)-catalyzed Azide-Alkyne Cycloaddition (CuAAC) procedure, also known as the Click reaction. The reaction between terminal alkynes ethynylbenzene 5 and 2-ethynylpyrazine 6 with substituted aryl azides 1-4 yielded the corresponding 1,2,3-triazole-hybrids 7-14. The synthesized products were analyzed using NMR (1H and 13C), mass spectrometry, and elemental analysis. The anticancer activities of the synthesized compounds were assessed in vitro against three cancer cell lines: colorectal carcinoma (HCT-116), hepatoblastoma (HePG-2), breast adenocarcinoma (MCF-7), and a normal human cell line (WI-38) through the MTT assay. Notably, compounds 10, 14, and 9 demonstrated the most potent inhibitory effects on colon, liver, and breast cancer cells, respectively, while maintaining low toxicity towards normal cells compared to doxorubicin. Moreover, the molecular dynamics simulations revealed that compound 10 demonstrated significant interactions with essential residues of the binding site, resulting in a stable complex throughout the entire simulation run. As a result of these findings, it can be concluded that these tetra-1,2,3-Triazole hybrids may prove to be promising candidates for development as novel anticancer agents.