Synthesis, Characterization, Molecular Docking Studies and Antimicrobial Activity of Azomethine Derivatives of 1,3-Substituted Pyrazoles

Abstract

Two different series of azomethine derivatives of 1,3-substitued pyrazoles were synthesized from the intermediates 3-(4-chlorophenyl)-1-phenyl-1H-pyrazole-4-carbaldehyde (3a) and 3-(furan-2-yl)-1-phenyl-1H-pyrazole-4-carbaldehyde (3b) by the condensation of various substituted anilines. The intermediates were obtained from the appropriate phenylhydrazones via Vilsmeier–Haack reaction. The synthesized compounds were characterized by IR, 1H NMR and MASS spectral studies. Molecular docking studies results revealed that 4a7 and 4a8 showed highest binding affinity against fungal target secreted aspartic proteinase (Sap) 1 (2QZW) and compounds 4a8 and 4a5 showed highest binding affinity against bacterial target glucosamine-6-phosphate synthase (2VF5). In vitro antimicrobial activity of corresponding azomethine derivatives were assessed on Gram-positive and Gram-negative bacteria. Antifungal activity was assessed on Candida albicans. The results revealed that six out of fifteen compounds screened have shown good antimicrobial activity. Among them, 4a1, 4a4, 4a6 and 4a7 shown good inhibition against Candida albicans.