1-butyl-3-methylimidazolium bromide mediated synthesis of eleven Schiff base compounds (1-11) bearing benzhydrazide moiety is carried out followed by their structural investigation based on ESI-Mass, UV-Vis, FTIR and ¹H NMR spectroscopic techniques. The antibacterial activity of the compounds was assessed against Bacillus licheniformis, Staphylococcus epidermidis, Pseudomonas syringae and Klebsiella pneumoniae. The DPPH assay was followed to check the antioxidant potential while BSA denaturation model was used to find the anti-inflammatory potency of the compounds. The Schiff bases are found to possess very good biological activities. Docking studies have also been conducted to understand the interaction between the ligands and the protein involved in antibacterial activity.