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

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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.

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Acknowledgements

The authors are grateful to Acharya Nagarjuna University for constant encouragement and the University Grant Commission (New Delhi, India) for providing a fellowship (BSR Meritorious Fellowship to N.R. [F.4-1/2006(BSR)/11-67/2008(BSR) dt. 13.01.2011) and CSIR, New Delhi for providing financial support for some chemicals (F.No. 02(198)/EMR-II. Dt. 14.11.2014). The authors are also very grateful to Surender Singh Jadav, Department of Pharmaceutical Sciences and Technology, Birla Institute of Technology, Jharkhand, India for his kind help with the docking study.

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Authors and Affiliations

  1. Department of Chemistry, Acharya Nagarjuna University, NNagar, Guntur, AP, 522510, India

    Navudu Ramesh, Mannem Gangadhara Rao, A. Vasu Babu & B. Hari Babu

  2. Department of Botany and Microbiology, Acharya Nagarjuna University, NNagar, Guntur, AP, 522510, India

    P. Nagababu & V. Umamaheswara Rao

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  1. Navudu Ramesh
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Correspondence to B. Hari Babu.

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Ramesh, N., Gangadhara Rao, M., Vasu Babu, A. et al. Synthesis, antibacterial activity, and docking studies of some novel N′-benzylidene-2-(2,4,5-trifluorophenyl)acetohydrazides. Res Chem Intermed 43, 4145–4164 (2017). https://doi.org/10.1007/s11164-017-2864-0

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