The synthesis and biological evaluation of a library of thirty differently substituted pyrazolo[3,4 b]pyridines bearing benzenesulfonamide moiety at position-1 and trifluoromethyl group at position-4 are reported. Fused heterocyclic system present in the target compounds (5a–j, 6a–j, and 7a–j) was constructed by refluxing various 5-aminopyrazoles (3a–c) with differently substituted trifluoromethyl-b-diketones (4a–j) in glacial acetic acid. All the target compounds (5–7) were evaluated for their in vitro antibacterial activity against four pathogenic bacterial strains namely, Staphylococcus aureus, Bacillus subtilis (Gram-positive), Escherichia coli, Pseudomonas aeruginosa (Gram-negative) and in vitro antifungal activity against two pathogenic fungal yeasts namely, Saccharomyces cerevisiae and Candida albicans.