The newly synthesized hetero annulated carbazoles were prepared in good yields and structurally characterized by all spectral means. The in vitro cytotoxicity was evaluated for all the synthesized compounds by MTT (3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide) assay against HeLa and MCF 7 and compared with the standard drug ellipticine. Compound 5b outperformed the standard drug ellipticine. All the compounds showed moderate to potent activity against the cell lines. The preliminary structure–activity relationships were carried out. In order to understand the nature of interactions of these molecules we carried out molecular docking studies using the protein kinase CK2 inhibitors. The docking results provided some useful information for the future design of more potent inhibitors.