The current treatment of Chagas disease is based on the use of two drugs, nifurtimox and benznidazole, which present limited efficacy in the chronic stage of the disease and toxic side effects. Although some progress has been made in the development of new drugs to treat this disease, the discovery of novel compounds is urgently required. In this work we report the synthesis and biological evaluation of 1,2,3-triazole-based analogues of benznidazole. A small series of 27 compounds was successfully synthesized via microwave-assisted copper(I)-catalyzed azide-alkyne cycloaddition (CuAAC) and ruthenium-catalyzed azide-alkyne cycloaddition (RuAAC) from N-benzyl-2-azidoacetamide (1) and a set of commercial terminal alkynes. Analogues 24 (IC50 40 μM) and 28 (IC50 50 μM) showed comparable activities to benznidazole (IC50 34 μM) against trypomastigote form and analogue 15 (IC50 7 μM) was found to be the most active. Regarding the cytotoxicity assessment of the series, most compounds were not cytotoxic. This work shows that the designed strategy is efficiently capable of generating novel benzindazole analogues and reveals one analogue is more active than benznidazole.