Design and synthesis of new 1,2,3-triazole-pyrazole hybrids as antimicrobial agents

Resumo

In the present study, a series of novel 1,2,3-triazoles derivatives (4a–4c) were synthesized by the 1,3-dipolar cycloaddition (click-reaction) of 1-phenyl-3-[2-(prop-2-yn-1-yloxy)phenyl substituted]-1H-pyrazole-4-carbaldehyade (3a–3c) with various aryl azides in the presence of sodium ascorbate and copper sulphate with high yields. The required precursors 3a–3c were synthesized by the reaction of 1-(2-hydroxy phenyl substituted)ethanones (1a–1c) with propargyl bromide via 1-[2-(prop-2-yn-1-yloxy)phenyl substituted] ethanone (2a–2c), followed by reaction with phenyl hydrazine. The newly synthesized 1,2,3-triazole-pyrazole derivatives were characterized by analytical and spectral data. All synthesized compounds were evaluated in vitro for their antibacterial and antifungal activity. The most active compounds 4a₅–4a₇ demonstrated a broad spectrum of antibacterial activity against all strains used for testing. Compounds (4a₄, 4b₁, 4c₁, 4c₂) demonstrated significant antifungal activity at the concentration of 10 μg/mL.