A series of novel (isopropylidene) uridine-[1,2,3]triazole hybrids (3a–3n) were efficiently synthesized via the copper-catalyzed azide–alkyne cycloaddition (CuAAC) from N-propargyl 2′,3′-O-(isopropylidene) uridine with different aryl azides. All the synthesized compounds were screened for their in vitro anticancer and antibacterial activities. The anticancer activity results revealed that compounds 3d and 3f have registered equipotent activity against MCF-7 and 3n has shown excellent activity against HeLa in comparison with the standard drug Cisplatin. Remaining compounds have shown moderate to good anticancer activity against MCF-7 and HeLa cell lines. The antibacterial activity screening results revealed that, compounds 3b and 3n have shown excellent inhibition against Escherichia coli and Bacillus subtilis, 3d against Proteus vulgaris, 3k against Staphylococcus aureus and 3l against S. aureus and B. subtilis have shown equipotent activity in comparison with the standard drug Streptomycin.