A series of 1,4-disubstituted pyrimidine-1,2,3-triazole phenyl derivatives were synthesized through Cu(I)-catalyzed click chemistry using N-(3-(6-amino-5-(2-(methyl(pr-yn-1-yl)amino)ethoxy)pyrimidin-4-yl)-5-fluoro-2-methylphenyl)-4-cyclopropyl-2-fluorobenzamide and various substituted aryl azides. The compounds were characterized using IR, ¹H NMR, ¹³C NMR, and HRMS techniques. Molecular docking studies assessed their anticancer, antioxidant, and antidiabetic activities against target proteins: human placental aromatase (PDB ID: 4GL7), human peroxiredoxin-5 (PDB ID: 1HD2), and glycogen phosphorylase receptor (PDB ID: 1NOI). Compounds 10a-o exhibited excellent binding scores ranging from -6.0 to -10.6 kcal/mol. Five compounds with favorable scores were selected for in vitro anticancer evaluation against the MDA-MB-231 breast cancer cell line, revealing notable activities for compounds 10i, 10l, and 10m with IC50 values of 73.30 μg/ml, 88.28 μg/ml, and 88.28 μg/ml, compared to doxorubicin (IC50= 1.96 μg/ml). For antioxidant activity, compounds 10b, 10c, 10h, and 10o demonstrated significant ABTS radical scavenging with IC50 values ranging from 6.649± 0.236 μM to 7.153± 0.234 μM, comparable to Trolox (IC50= 7.138±0.053 μM). Compounds 10a, 10f, 10i, 10j, and 10l showed prominent anti-diabetic activity with IC50 values around 5.675 ± 0.168 μM to 5.893 ± 0.175 μM, relative to metformin (IC50= 5.309 ±0.034 μM). ADMET analysis confirmed the drug-likeness and pharmacokinetic properties, indicating the potential of these derivatives as anticancer, antioxidant, and antidiabetic agents.