New acrylamide compounds based on 4-aminoantipyrine were synthesized. 4-Acetaminoantipyrine was synthesized and its reactivity with salicylic aldehyde, vanillin, isovanillin and 5-methoxysalicylaldehyde with the formation of new N-(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)-3-(aryl)acrylamides was investigated. In addition, synthesized acrylamides were screened for ADME studies to elucidate their properties. The antimicrobial and antioxidant activitiy of the newly synthesized compounds were exceptionally high, surpassing the performance of the reference standard drug. Molecular docking simulations further confirmed these results, highlighting the heightened activity attributed to the substitute groups on the aromatic rings with different proteins and showed different interactions, confirming their biological evaluation. The optimization of target compounds using the DFT/B3LYP/6-311G(d) basis set demonstrated their stability and provided insights into their physical descriptors—Electrostatic Potential (ESP) and Molecular Electrostatic Potential (MEP). The analysis revealed both electrophilic and nucleophilic characters, showcasing their versatile binding capabilities in various pockets and confirming the biological results.