Benzamide based structural analogues 1–15 were synthesized, and evaluated for α-glucosidase inhibition activity in vitro for the first time. Compounds 1–9 were found to be known, while compounds 10–15 were found to be new. However, to the best of our knowledge we are reporting α-glucosidase inhibitory activity of these bezamide derivatives of thiourea for the first time. Compounds 1, 3, 6–8, 10–14 were found to be potent inhibitors of α-glucosidase within IC₅₀ range of 20.44–333.41 µM, in comparison to the standard inhibitor, acarbose (IC₅₀ = 875.75 ± 2.08 µM). Mode of the enzyme inhibition was determined on the basis of kinetic studies which demonstrated that compounds 8, and 10 were non-competitive and competitive inhibitors of α-glucosidase enzyme, respectively. These compounds were also evaluated for their DPPH radical scavenging activity, and cytotoxicity against 3T3 mouse fibroblast cell lines. All synthesized compounds showed a significant to moderate DPPH radical scavenging activity and appeared to be non-cytotoxic except compound 9 which showed cytotoxicity against 3T3 normal mouse fibroblast cell lines. A single crystal X-ray and Hirshfeld Surface analysis of a representative compound is also presented.