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Synthesis, antimicrobial activity and molecular docking study of novel alpha-(diphenylphosphoryl)- and alpha-(diphenylphosphorothioyl)cycloalkanone oximes

Nejib Jebli, Selma Hamimed, Kristof Van Hecke (UGent) , Jean-Francois Cavalier and Soufiane Touil
(2020) CHEMISTRY & BIODIVERSITY. 17(8).
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Abstract
A series of novel alpha-(diphenylphosphoryl)- and alpha-(diphenylphosphorothioyl)cycloalkanone oximes have been synthesized in search for novel bioactive molecules. Their structures were characterized by various spectroscopic methods including IR, NMR (H-1,P-31,C-13), mass spectrometry and single crystal X-ray diffraction. The newly synthesized phosphorus-containing oximes were screened for theirin vitroantimicrobial activity against Gram-positive bacteria (Staphylococcus aureusandBacillus subtilis), Gram-negative bacteria (Escherichia coliandSalmonella typhimurium) and fungal strains (Candida albicansandCandida glabrata). The biological assays showed that all the studied compounds exhibited high antibacterial and antifungal activities at only 0.1-2.1 mu g/mL.In silicomolecular docking studies in FabH enzyme active site were performed in order to predict the possible interaction modes and binding energies of the drug candidates at the molecular level.
Keywords
BECKMANN REARRANGEMENT, DERIVATIVES, SYNTHASE, FABH, ENAMINES, KETO, oximes, phosphine oxides, phosphine sulfides, phosphonyl oximes, antibacterial activity, antifungal activity, molecular docking

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MLA
Jebli, Nejib, et al. “Synthesis, Antimicrobial Activity and Molecular Docking Study of Novel Alpha-(Diphenylphosphoryl)- and Alpha-(Diphenylphosphorothioyl)Cycloalkanone Oximes.” CHEMISTRY & BIODIVERSITY, vol. 17, no. 8, 2020, doi:10.1002/cbdv.202000217.
APA
Jebli, N., Hamimed, S., Van Hecke, K., Cavalier, J.-F., & Touil, S. (2020). Synthesis, antimicrobial activity and molecular docking study of novel alpha-(diphenylphosphoryl)- and alpha-(diphenylphosphorothioyl)cycloalkanone oximes. CHEMISTRY & BIODIVERSITY, 17(8). https://doi.org/10.1002/cbdv.202000217
Chicago author-date
Jebli, Nejib, Selma Hamimed, Kristof Van Hecke, Jean-Francois Cavalier, and Soufiane Touil. 2020. “Synthesis, Antimicrobial Activity and Molecular Docking Study of Novel Alpha-(Diphenylphosphoryl)- and Alpha-(Diphenylphosphorothioyl)Cycloalkanone Oximes.” CHEMISTRY & BIODIVERSITY 17 (8). https://doi.org/10.1002/cbdv.202000217.
Chicago author-date (all authors)
Jebli, Nejib, Selma Hamimed, Kristof Van Hecke, Jean-Francois Cavalier, and Soufiane Touil. 2020. “Synthesis, Antimicrobial Activity and Molecular Docking Study of Novel Alpha-(Diphenylphosphoryl)- and Alpha-(Diphenylphosphorothioyl)Cycloalkanone Oximes.” CHEMISTRY & BIODIVERSITY 17 (8). doi:10.1002/cbdv.202000217.
Vancouver
1.
Jebli N, Hamimed S, Van Hecke K, Cavalier J-F, Touil S. Synthesis, antimicrobial activity and molecular docking study of novel alpha-(diphenylphosphoryl)- and alpha-(diphenylphosphorothioyl)cycloalkanone oximes. CHEMISTRY & BIODIVERSITY. 2020;17(8).
IEEE
[1]
N. Jebli, S. Hamimed, K. Van Hecke, J.-F. Cavalier, and S. Touil, “Synthesis, antimicrobial activity and molecular docking study of novel alpha-(diphenylphosphoryl)- and alpha-(diphenylphosphorothioyl)cycloalkanone oximes,” CHEMISTRY & BIODIVERSITY, vol. 17, no. 8, 2020.
@article{8694715,
  abstract     = {{A series of novel alpha-(diphenylphosphoryl)- and alpha-(diphenylphosphorothioyl)cycloalkanone oximes have been synthesized in search for novel bioactive molecules. Their structures were characterized by various spectroscopic methods including IR, NMR (H-1,P-31,C-13), mass spectrometry and single crystal X-ray diffraction. The newly synthesized phosphorus-containing oximes were screened for theirin vitroantimicrobial activity against Gram-positive bacteria (Staphylococcus aureusandBacillus subtilis), Gram-negative bacteria (Escherichia coliandSalmonella typhimurium) and fungal strains (Candida albicansandCandida glabrata). The biological assays showed that all the studied compounds exhibited high antibacterial and antifungal activities at only 0.1-2.1 mu g/mL.In silicomolecular docking studies in FabH enzyme active site were performed in order to predict the possible interaction modes and binding energies of the drug candidates at the molecular level.}},
  author       = {{Jebli, Nejib and Hamimed, Selma and Van Hecke, Kristof and Cavalier, Jean-Francois and Touil, Soufiane}},
  issn         = {{1612-1872}},
  journal      = {{CHEMISTRY & BIODIVERSITY}},
  keywords     = {{BECKMANN REARRANGEMENT,DERIVATIVES,SYNTHASE,FABH,ENAMINES,KETO,oximes,phosphine oxides,phosphine sulfides,phosphonyl oximes,antibacterial activity,antifungal activity,molecular docking}},
  language     = {{eng}},
  number       = {{8}},
  pages        = {{12}},
  title        = {{Synthesis, antimicrobial activity and molecular docking study of novel alpha-(diphenylphosphoryl)- and alpha-(diphenylphosphorothioyl)cycloalkanone oximes}},
  url          = {{http://doi.org/10.1002/cbdv.202000217}},
  volume       = {{17}},
  year         = {{2020}},
}
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