In the modern world, where there is a growing demand for new substances with anticancer and antifungal activities, Schiff bases and phthalimide derivatives, which exhibit a wide diversity of biological activity, have become the focus of new therapeutic research studies. Accordingly, this study examined the anti-proliferative effects of two distinct compounds synthesized by cyclobutane substitution on breast cancer and liver cancer cell lines, which are two major cancer types, were investigated with MTT method and their antifugal activities on C. albicans were evaluated with disk diffusion method. Minimum inhibitory concentrations of the compounds against C. albicans were also determined in the scope of the study. The results revealed that the synthesized Schiff base was more effective on the breast cancer cell line MCF7, whereas the phthalimide-derivative was more effective against the liver cancer cell line Mahlavu. Besides, according to the data related to the antifungal properties of the compounds, it can be inferred that both compounds are suitable for further investigation as potential building blocks for the creation of novel and efficient antifungal medications.