The azoles pharmacophore is still considered a viable lead structure for the synthesis of more efficacious and broad spectrum antimicrobial agents. Potential antibacterial, antifungal and anti-inflammatory activities are encountered with Schiff’s bases of triazole. Therefore, this study presents the synthesis, characterization and evaluation of antimicrobial & anti-inflammatory activity a new series of Schiff’s bases of trizoles that are structurally related to the famous active azoles pharmacophore. A detailed discussion of the structural elucidation of the newly synthesized compounds was confirmed by elemental analysis, melting point, Thin Layer Chromatography, FT-IR, NMR and Mass spectra. Antimicrobial evaluation revealed that compounds were able to display variable growth inhibitory effects on the tested Gram- positive and Gram-negative bacteria with special efficacy against the Gram-negative strains. Some compounds showed reasonable anti-inflammatory activity.