In order to explore the therapeutic potential of pyrazole-based analogues, six Synthesis, anti-inflammatory, antimicrobial and antioxidant evaluation of novel N-((3-(substituted phenyl)-1-phenyl-1H-pyrazol-4-yl) methylene) naphthalen-1-amines (3a-f) were synthesized using multistep synthetic methodology. Structural elucidation of all synthesized molecules was performed by using IR and 1H NMR spectral reports. All molecules were accessed for their antimicrobial potential against a panel of four bacterial strains and one fungal strain. Results of in vitro antimicrobial data revealed compounds 3d as most potent antibacterial agent towards E. coli, S. aureus and B. subtilis with MIC values of 6.25 µg/mL while Compounds 3b, 3c, 3d and 3e as most active antifungal agents against tested fungal species i.e., R. oryaze (MIC=3.125 µg/mL). Further, in vitro anti-inflammatory antioxidant potential was evaluated for synthesized molecules in which compound 3d have powerful anti-inflammatory and antioxidant profile with IC50 values of 0.06289 and 0.024765 µmol/ml