Introduction: Now days, cancer is one of the most dangerous disease and is a widest topic for research as a challenging task is to develop new entities with selectivity towards cancerous cells. Compounds containing a benzimidazole moiety are an important member of the nitrogen containing heterocyclic ring system since it confers surprisingly good anticancer properties. Methodology: A series of 1H-Benzimidazole-5-carboxamide compounds have been designed and synthesized as per synthetic scheme. Newly synthesized compound(s) were characterized by their infrared, proton nuclear magnetic resonance and mass spectral analysis. In order to evaluate their biological activity, these compounds were tested for their anticancer potential. Furthermore, the experimental results were supported by molecular docking study. Result and Discussion: The results revealed that all newly synthesized compounds were exhibited moderate to potent anticancer activity. In case of potent anticancer activity, compound no. 5 and 3 gives prominent activity with comparison of all synthesized compounds. Conclusion: In conclusion, we have designed, synthesized and characterized an interesting and biologically important series of Benzimidazole bridged analogues of Benzimidazole derivatives derivatives. Most of the synthesized compounds were found more active as comparison with each other as manifested by theoretical as well as experimental results.