This paper elicits the synthesis of twenty five 1,4-disubstituted 1,2,3-triazole analogs (5a–5y) comprising thioether and ester linkages from aryl(prop-2-yn-1-yl)sulfanes and benzyl 2-azidoacetates employing Cu(I) catalyzed Huisgen 1,3-dipolar cycloaddition. Structures of synthesized compounds were elucidated by spectroscopic techniques like FTIR, 1H NMR, 13C NMR, and HRMS. Newly synthesized compounds were screened for in vitro antimalarial evaluation against P. falciparum strain and microbicidal potential against B. subtilis, S. epidermidis, E. coli, P. aeruginosa, C. albicans, and A. niger. Some of synthesized triazoles displayed moderate antimalarial activity against tested strain, while, the compounds 5i and 5n were found to exhibit significant inhibitory activity against most of the tested microbial strains.