Several new imidazole-5(4H)-one analog was synthesized using multi-step synthesis. All the synthesized compounds were characterized using FT-IR, 1H-NMR, Mass spectroscopy, and microanalysis to confirm their chemical structure. Molecular properties of the title compounds were predicted using Molinspiration online tool and binding studies of the title analogs against COX-1 & COX-2 were predicted by the molecular docking method. All novel imidazole-5(4H)-one analog were tested for their in-vivo anti-inflammatory activity using carrageenan-induced paw edema test in Wistar rats. Varying degree (weak to excellent) of anti-inflammatory activity was displayed by title compounds. In addition, in vitro anticancer potency of test compounds was estimated by the MTT assay method and found that most of the tested analogs were found to be inactive at 10 µM concentration against the tested cell lines. Among twelve tested title compounds, 2-methyl-1-(4-methyl piperazine-1-yl)-4-(naphthalen-1-ylmethylene)-1H-imidazol-5(4H)-one AL01, and 4-benzylidene-2-methyl-1-(4-methylpiperazin-1-yl)-1H-imidazol-5(4H)-one AL02 displayed more potent anti-inflammatory activity which is slightly higher than reference diclofenac.