EGFR and HER2 protein tyrosine kinases are expressed in a variety of cancers, including ovarian, breast, colon, and prostate subtypes. Lapatinib, an FDA-approved treatment for breast cancer, has acquired resistance due to various undetermined causes. Therefore, we synthesized novel TAK-285 derivatives (9a–h) by hybridizing 4-anilinequinazoline, a promising chemical moiety for EGFR/HER2 dual inhibition, with a 2-nitroimidazole group that is effective in tumor treatment. Each structure was confirmed by ¹H NMR,¹³C NMR, and HRMS, and 9f, which showed the best kinase inhibition, was further studied. Compound 9f exhibited IC₅₀ values of 2.3 nM against EGFR and 234 nM against HER2. In addition, MTT assays against human prostate cancer cell lines PC3 and 22RV1 were performed, and 9f showed the best results. When the cell cycle of 22RV1 and PC3 cells was analyzed, it was found that the G2/M phase inhibited up to 62.74% and 49.43%. In addition, cells were stained with Annexin V and DAPI and cell fluorescence analysis was performed using ADAMI LS, and 22RV1 showed early apoptosis, late apoptosis phase, and PC3 cells showed early apoptosis and late apoptosis phase compared to cancer cells in the control group.