In this work, some new 2-[(3,4-dichlorophenyl)methyl]-1H-benzimidazole derivatives containing different five-membered heterocycles like 1,3,4-oxadiamle, 1,3,4-triazole, and 1,3,4-thiadiazole moieties were designed and efficiently synthesized starting from 2-[(3,4-dichlorophenyl) methyl ]-1H-benzimidazole. The products were screened for their in vitro antioxidant and alpha-glucosidase inhibitory activities. Among the synthesized compounds, some of them showed efficient alpha-glucosidase inhibition with IC50 values ranging between 16.05 +/- 0.94 and 77.02 +/- 1.12 mu g/mL when they were compared with the standard alpha-glucosidase inhibitor acarbose having IC50 value 12.04 +/- 0.68 +/- g/mL. The antioxidant activity of all products was screened by using various in vitro antioxidant assays, including CUPric Reducing Antioxidant Capacity (CUPRAC) and Ferric Reducing Antioxidant Power (FRAP) assays. Also, the radical scavenging activities of the products were assayed by using the ARTS method.