Inspired by the literature and the lack of anticancer activity studies of benzimidazolone hybrid compounds, in this work, we have synthesized benzimidazolone-conjugated biscoumarin and piperazine and investigated their anticancer activities against breast cancer (MCF-7), lung cancer (A549), and cervical cancer (HeLa) cell lines and performed an in silico molecular docking study targeting the critical oncological enzymes VEGFR-2 and CDK4 to understand the potential mechanism of action. Here, CDK4 is linked to breast carcinoma.