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The employment of privileged scaffolds in medicinal chemistry supplies scientists with a solid start in the search for new and improved therapeutic molecules. One of these scaffolds is the imidazole ring, from which several derivatives have shown a wide array of biological activities. A series of 2,4,5-triphenyl imidazole derivatives were synthesized, characterized, and evaluated in vitro as antioxidant molecules using 1,1-diphenyl-2-picrylhydrazyl (DPPH^.) and 2-2′-azino-bis-(3-ethylbenzothiazoline-6-sulfonate) (ABTS^.+) assays, acetylcholinesterase (AChE) and xanthine oxidase (XO) inhibitors as well as antiproliferative agents. Additional in silico studies such as docking and determination of their absorption, distribution, metabolism, and excretion (ADME) properties were calculated. Compounds <b>3</b> and <b>10</b> were the most active antioxidants in both the DPPH and ABTS assays (EC₅₀ of 0.141 and 0.174 mg/mL, and 0.168 and 0.162 mg/mL, respectively). In the enzymatic inhibition, compound <b>1</b> showed the best activity, inhibiting 25.8% of AChE at a concentration of 150 μg/mL, and compound <b>3</b> was the most active XO inhibitor with an IC₅₀ of 85.8 μg/mL. Overall, against the six different evaluated cancerous cell lines, molecules <b>2</b>, <b>10</b>, and <b>11</b> were the most antiproliferative compounds. In silico predictions through docking point out <b>11</b>, and ADME analysis to <b>11</b> and <b>12</b>, as good candidates for being lead compounds for further derivations.