Two novel Schiff bases were synthesized from 4-amino-N-(4-aminophenyl)benzamide (DABA) and investigated after the spectral characterization techniques. Density functional theory (DFT) and molecular docking studies were conducted initially for the molecules for drug suitability. The toxicity of the synthesized molecules was evaluated using brine shrimp and 50% mortality concentrations of both the Schiff bases were examined with standard vincristine sulphate. Then, the antimicrobial activity was studied against selected bacterial strains such as E. coli, K. pneumoniae, S. typhimurium and P. mirabilis. The biological efficacy also extended to antioxidant study and the results showed that the inhibition concentrations between 150 and 305 µg/mL, which are in the toxicity limit. Out of two molecules, 2,4-dihydroxy group substituted Schiff bases showed better antimicrobial, antidiabetic and antioxidant activities. © 2024 Elsevier B.V., All rights reserved.