Synthesis and antibacterial evaluation of pyrazolines carrying (benzyloxy)benzaldehyde moiety

Abstract

A novel series of 1,2,3-triazole-linked pyrazoline analogues were prepared by the reaction of 3-(4-(benzyloxy)phenyl)-1-(1-(arylphenyl)-5-methyl-1H-1,2,3-triazol-4-yl)prop-2-en-1-one with hydrazine hydrate in the presence of glacial acetic acid medium. The structures of the newly synthesized pyrazoline derivatives were established by elemental analysis, FT-IR, sup(1)H NMR, sup(13)C{sup(1)H} NMR, and mass spectral analysis. In addition, synthesized compounds DFT calculations and 3D structures of the synthesized compounds were performed using Gaussian 09 software, hybrid models and MM2 force techniques were used to obtain energy minimized structures. The antibacterial activities of the synthesized pyrazolines were determined against Gram-positive and Gram-negative strains. Among them, compounds with meta-chloro substitution on phenyl ring of pyrazoline showed the highest magnitude of inhibition against Pseudomonas aeruginosa and bromo substitution on para position of phenyl ring exhibited highest magnitude of inhibition against Staphylococcus aureus.