Schiff bases have been important compounds ever since their discovery and are both found in nature and synthesized in the laboratory. They participate in a variety of synthetic processes and possess desirable biological activity, including antibacterial, anti-inflammatory, antioxidant, and anticancer activity, among others. In this study, eight Schiff bases derived from the reaction of 4-aminoantipyrine with various cinnamaldehydes have been synthesized and characterized. All derivatives were tested in vitro on several human carcinoma cell lines to determine their antitumor activity and against different bacteria strains of clinical and food industry importance to evaluate their antibacterial activity. Various of the Schiff bases evaluated inhibited tumor cell growth in a dose-dependent manner. The compound that exhibited the most activity against all cell lines had IC₅₀ values of less than 18 μM, and the compound with the best therapeutic index presented IC₅₀ values between 24 – 48 μM. On the other hand, during the evaluation of the antibacterial activity, only two Schiff base derivatives showed interesting antibacterial effects, with MIC values ranging from 250 – 15.6 μM. These two Schiff bases derivatives mainly exhibited a bacteriostatic effect against most of the studied bacterial strains. It is interesting to note that the same Schiff base presents the best activity in both biological evaluations.