A synthesis of bis-and poly(benzimidazoles) as well as bis-and poly(benzothiazoles) was attempted using different protocols. The best results were obtained by employing the reaction of the appropriate bis-or poly(aldehydes) with o-phenylenediamine or 2-aminothiophenol, respectively, in ethanol at reflux in the presence of NaHSO 3 . The anticancer activities of the synthesized compounds were evaluated against human breast adenocarcinoma cell line (MCF-7), liver cancer cell line (HepG-2), and epithelial colorectal adenocarcinoma cells (CaCO-2). Hexakis(benzothiazole) was found to exhibit the highest activity against HepG-2 and MCF-7 cell lines with IC 50 values of 21.16 and 13.25 μM, respectively.