Synthesis, antibacterial activity, and docking studies of some novel N′-benzylidene-2-(2,4,5-trifluorophenyl)acetohydrazides

Synthesis, antibacterial activity, and docking studies of some novel... 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. http://www.deepdyve.com/assets/images/DeepDyve-Logo-lg.png Research on Chemical Intermediates Springer Journals

Synthesis, antibacterial activity, and docking studies of some novel N′-benzylidene-2-(2,4,5-trifluorophenyl)acetohydrazides

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Publisher
Springer Netherlands
Copyright
Copyright © 2017 by Springer Science+Business Media Dordrecht
Subject
Chemistry; Catalysis; Physical Chemistry; Inorganic Chemistry
ISSN
0922-6168
eISSN
1568-5675
D.O.I.
10.1007/s11164-017-2864-0
Publisher site
See Article on Publisher Site

Abstract

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.

Journal

Research on Chemical IntermediatesSpringer Journals

Published: Jan 28, 2017

References

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