A new series of phenylalanine‐derived carboxamides with sulfonamide functionality is designed, synthesized, and assessed for their in silico studies, in vitro antimalarial, and antioxidant activities. The interaction of 4‐nitrobenzene sulfonyl chloride with phenylalanine in a basic aqueous solution yielded an intermediate ((4‐nitrophenyl)sulfonyl)phenylalanine. The reaction of various cyclic amines with the intermediate, utilizing phenylboronic acid as the coupling agent, yielded the carboxamides derivatives. The derived‐carboxamides passed in silico test and fulfilled all the allowed ranges for molecular descriptors. Optimization was achieved before compounds were deployed as ligands in molecular docking studies using density functional theory utilizing the functional B3LYP and the basis set 6–31G**. The docking experiments were done on the active site of FKBP35 binding domain of Plasmodium falciparum for antimalarial impact whereas that of antioxidants was performed on the active site of PDB ID:IXAN. The computational antimalarial and antioxidant study demonstrated that the compounds displayed a high binding affinity with the target protein residues via hydrogen bonding, π‐π, π‐alkyl, π‐sigma, and π‐cation bonding interactions. Additionally, the new compounds were evaluated for in vitro antimalarial and antioxidant properties. The screening findings suggest that the new compounds exhibit effective antimalarial and antioxidant action compared to traditional medicines.