Chalcones have been reported to have a broad range of biological activities such as antimalarial, antibacterial, antitumor, antioxidant, antihyperglycemic, and anti-HIV. An enhancement of the antitumor activity has been observed when one of the aromatic rings is replaced with ferrocene, however, the mechanism of action is still uncertain. Therefore, our research explores and chemically modifies the structure of ferrocenyl chalcone-based scaffolds to study their anticancer and antioxidant activities. This study will also yield information regarding possible mechanisms of action. Among the proposed modifications to the ferrocenyl chalcone-based scaffolds is the incorporation of heterocyclic moieties. This can be afforded either by introducing a heterocyclic aromatic substituent or functionalizing the α,βunsaturated system. Another modification is to form ammonium or pyridinium salts to increase water solubility. All compounds are extensively characterized by Infrared, 1H, and 13C-NMR spectroscopy, UV-Vis spectrophotometry, single-crystal x-ray diffraction, and cyclic voltammetry. Antioxidant activity is studied applying DPPH radical scavenging assay and antitumor by MTS colorimetric cell proliferation assay.