Free radicals are particles that have an unpaired electron. If they produced in high level in our bodies, they can produce damage to lipids, proteins, and DNA. Antioxidants are any compounds that can incorporate free radicals in a safe way, cease the reaction, and switch them to a risk-free molecule by donating a proton. On the other side, the infectious diseases are among the chief causes of death worldwide, and antimicrobial resistance has been regularly reported globally. Thus, these complications necessitate the investigation for new therapies with potential antioxidant and antimicrobial activities. This study aims to design, synthesize and evaluate the antioxidant and antimicrobial activities of new N,N'-(dialkoyl/diaroyl)-4,4'-methylenedianiline compounds. These compounds were synthesized by the reaction of carboxylic acids with 4,4'-methylenedianiline in presence of dicyclohexylcarbodiimide (DCC) as coupling agent. The structures of the synthesized compounds were characterized on the basis of the physical and spectral data. The antioxidant activity of these compounds was evaluated by testing their free radical scavenging activity of DPPH and H2O2 and their antimicrobial activity was evaluated via measuring the inhibition zones in the disk diffusion method. The tested synthesized compounds show varied antioxidant and antimicrobial activities. The hydroxyl and the amide moieties in the synthesized compound possess similar potent antioxidant activities. The fluoro-aromatic compound showed potent antibacterial and antifungal activities. While the chloro aliphatic and aromatic compounds showed only antibacterial activity. Whereas fluoro-aromatic compounds and compounds with the ether group exposed a potent antifungal activity.