A facile and convenient protocol is developed for designing new heterocyclic compounds using nontoxic, simple, and eco-friendly methods.  A group of novel compounds containing either pyrazole or pyranopyrazole moieties was synthesized using 2-(5-oxo-4, 5-dihydro-1H-pyrazol-3-yl)-N-phenylacetamide (1a,b) as a precursor. The structure of the prepared compounds; namely pyranopyrazole derivatives 2 and pyrazole derivatives 3-6 was elucidated using different spectroscopic methods (such as FTIR, ¹H-NMR, Mass spectroscopy, and ¹³C-NMR) as well as elemental analyses. Consequently, the newly prepared compounds were all evaluated against different human pathogenic bacterial strains such as Escherichia coli, Staphylococcus aureus, Pseudomonas aeruginosa, and Bacillus subtilis using the commercial bactericide chloramphenicol as a reference. Most of the tested compounds showed moderate to high antibacterial activity. Molecular docking study was performed to predict binding affinities and the modes of interactions between the synthesized ligands and the active site of the topoisomerase IV. Presumably, the obtained results provide valuable information for designing, developing, and synthesizing novel heterocyclic scaffolds with enhanced pharmacological applications as antibacterial materials.