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Synthesis, characterization, antimicrobial activity and ultrastructure of the affected bacteria of new quinoline compounds

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Abstract

The reaction on 8-hydroxy quinoline-7-aldehyde azo compounds (HL n ) (where n = 1–5) with 4-amino-1,2-dihydro-2,3-dimethyl-1-phenylpyrazol-5-one to obtain HL n (where n = 6–10) have been characterized by means of TLC, melting point and spectral data, such as IR, 1H NMR, mass spectra and thermal studies. The X-ray diffraction patterns of two starting materials 8-hydroxy quinoline-7-aldehyde (start 1), 4-amino-1,2-dihydro-2,3-dimethyl-1-phenylpyrazol-5-one (start 2) and the ligands (HL5,10) are investigated in powder form. All the ligands have been screened for their antimicrobial activity against four local bacterial species, two Gram-positive bacteria (Bacillus cereus and Staphylococcus aureus) and two Gram-negative bacteria (Escherichia coli and Klebsiella pneumoniae) as well as against four local fungi; Aspergillus niger, Alternaria alternata, Penicillium italicum and Fusarium oxysporium. The results show that the azo ligands (HL n ) (where n = 1–5) have no antimicrobial activity against bacteria and fungi while most azomethine ligands (HL n ) (where n = 6–10) are good antibacterial agents against E. coli and K. pneumoniae as well as antifungal agents against P. italicum and A. alternata. The results were compared to standard substances (start 1) and (start 2). Among the azomethine ligands, HL10 was the most effective against the most microorganisms tested. The size of clear zone was ordered as p-(OCH3 < CH3 < H < Cl < NO2) as expected from Hammett’s constant (σ R). Also, the ultrastructure study of the affected bacteria confirmed that HL8 is good antibacterial agent against E. coli and S. aureus.

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Acknowledgments

The authors would like to thank Prof. Dr. Nabila El-Sayed Abdel Meguid Prof. Emeritus of Cytology and Cytochemistry, Zoology Department, Faculty of Science, Alexandria University, Egypt and Miss N.F. Omar, Botany Department, Faculty of Science, Damietta University, Egypt for their help during testing antimicrobial activities and ultrastructure study.

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Authors and Affiliations

  1. Botany Department, Faculty of Science, Damietta University, Damietta, Egypt

    M. I. Abou-Dobara

  2. Chemistry Department, Faculty of Science, Damietta University, Damietta, Egypt

    A. Z. El-Sonbati, M. A. Diab, A. A. El-Bindary & S. G. Nozha

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  1. A. Z. El-Sonbati
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  2. M. I. Abou-Dobara
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  3. M. A. Diab
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  4. A. A. El-Bindary
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  5. S. G. Nozha
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Correspondence to A. Z. El-Sonbati.

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On behalf of the authors of our paper entitled “Dielectrical properties and conduction mechanism of quinoline Schiff base and its complexes”, we certify that this paper is abstracted from our own work. This work is carried out in our laboratory and the obtained results have not been published in any journals. We have not received any grant from any agencies or company. We state that we do not have any conflict of interest with anyone.

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S. G. Nozha: Abstracted from her Ph.D. Thesis.

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El-Sonbati, A.Z., Abou-Dobara, M.I., Diab, M.A. et al. Synthesis, characterization, antimicrobial activity and ultrastructure of the affected bacteria of new quinoline compounds. Res Chem Intermed 42, 6449–6481 (2016). https://doi.org/10.1007/s11164-016-2474-2

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