A series of novel 3-phenyl-1-(4-(4-((4-(1,4,5-triphenyl-1H-imidazol-2-yl)phenoxy)methyl)-1H-1,2,3-triazol-1-yl)phenyl)prop-2-en-1-one derivatives 6a–j were synthesized in click chemistry reaction conditions and evaluated in silico by docking studies to recognize their hypothetical binding motif with cyclooxygenase-1 and cyclooxygenase-2. All docked compounds exhibited good docking scores in the range from 208.357 to 161.285 as compared with 145.934 for indomethacin, and 168.763 to 147.904 as compared with 145.934 for ibuprofen. Among all the tested compounds, 6b showed good docking score and good interactions with binding-site residues of the COX proteins.