Two series of diversely substituted 1-(3,5-dimethyl-4-(substitutedphenyldiazenyl)-1Hpyrazol-1-yl)-2-((2-methylquinolin-8-yl)oxy)ethanones (8a-g) and 3-methyl-1-(2-((2-methylquinolin-8-yl)oxy)acetyl)-4-(2-substitutedphenylhydrazono)-1H-pyrazol-5(4H)-ones (9a-h) were synthesized. All the newly synthesized compounds were characterized by IR, 1 H NMR, 13 C NMR, Mass and chemical analysis. The compounds were evaluated for their in vitro antibacterial activity against some Gram-positive bacteria, Staphylococcus aureus, Bacillus subtilis, Gram-negative bacteria, Escherichia coli, Pseudomonas aeruginosa, Salmonella typhi and screened for antifungal activity against Aspergillus niger, Ustilago maydis using the agar disc diffusion method. All the tested compounds showed significant antibacterial activity against both the strains with compounds 8d and 9d being more potent.