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In the present investigation, in order to identify GI-safe anti-inflammatory and analgesic agents, a series of novel 1, 2 and 5-substituted benzimidazole derivatives were synthesized and biologically evaluated. The results demonstrated that the compounds 3b, 4b, and 5b could serve as gastroprotective lead compounds for developing a novel class of potent as well as orally active anti-inflammatory and analgesic agents in the future research.