In the present study, novel 5-substituted tetrazole derivatives bearing the sulfonamide group were synthesized using an azide-nitrile cycloaddition reaction. The easy availability of the inexpensive starting materials, avoiding isolation and handling of hazardous organic azide, and mild reaction conditions make this synthetic protocol a valuable tool for the synthesis of functionalized tetrazole derivatives. All reactions proceeded smoothly to achieve the corresponding 5-substituted tetrazole derivatives 5a-f in moderate to good yields (32-85%) using ZnBr2 as a catalyst and green solvent system H2O/2-propanol. The structure of all products was confirmed by FT-IR, 1HNMR, and 13CNMR analysis. Furthermore, we used molecular docking and ADMET studies to investigate the possible drug-likeness of the synthesized molecules 5a-f, revealing that some molecules are the most promising drug-like molecules out of the seven synthesized molecules. Antifungal activity of the compound 5c against standard strains of pathogenic fungi was also investigated in the final section of study.