An improved method was developed for synthesis of 2,4,5-trifluorobenzohydrazide derivatives through condensation of trifluorophenylacetohydrazide with different aryl aldehydes in ethanol with 70% perchloric acid as catalyst. The developed method is efficient in terms of shorter reaction time, easy workup, and purity of final products. We synthesized a total of 25 molecules and screened them for antibacterial activity. Among the synthesized compounds, 4q showed good antibacterial activity against Streptococcus mutans MTCC 497 and Staphylococcus aureus MTCC 737 [50% inhibition concentration (IC50): 30 and 35 µg/mL, respectively], followed by compound 4c (IC50: 45 µg/mL) against Streptococcus mutans MTCC 497 as well as Salmonella enterica MTCC 3858. Molecular docking study employing glucosamine 6-phosphate deaminase (NagB) enzyme (PDB: 2RI1) revealed that the Glide scores of the present ligands played a role. Compounds with 2-NO2, 4-(NCH3)2, and 3,4-di-OH functional groups on the benzylidene ring (4e, i, m) exhibited significant Glide score of −8.2 kcal/mol.
Research on Chemical Intermediates – Springer Journals
Published: Jan 28, 2017
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