Experimental and computational investigation of Z/E isomerism, X-ray crystal structure and molecular docking study of (2-(hydroxyimino)cyclohexyl)diphenylphosphine sulfide, a potential antibacterial agent - Archive ouverte HAL Access content directly
Journal Articles Journal of Molecular Structure Year : 2020

Experimental and computational investigation of Z/E isomerism, X-ray crystal structure and molecular docking study of (2-(hydroxyimino)cyclohexyl)diphenylphosphine sulfide, a potential antibacterial agent

Nejib Jebli
  • Function : Author
Youssef Arfaoui
  • Function : Author
Kristof van Hecke
  • Function : Author
Soufiane Touil

Abstract

(2-(hydroxyimino)cyclohexyl)diphenylphosphine sulfide [C18H20NOPS (2)] is a novel oxime derivative that has been identified, in a recent work from our group, as a potential antibacterial agent. Herein, we report the in-depth structural analysis of compound (2) by using various spectroscopic tools including FT-IR, NMR (1H, 31P, 13C), mass spectrometry and single crystal X-ray diffraction, which indicate that it is obtained as a mixture of Z and E isomers. The different mechanisms, inversion, rotation, or mixed inversion-rotation, by which could occur the Z/E isomerization, have been investigated computationally with DFT method. Total and frontier molecular orbitals energies for both isomers were derived in order to gain more insights into their relative stabilities and biological activities. In silico molecular docking studies in E. coli FabH enzyme active site were also performed to predict the possible interaction modes and binding energies for both Z and E isomers as compared with those of a reference FabH inhibitor.
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Dates and versions

hal-03046712 , version 1 (08-12-2020)

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Nejib Jebli, Youssef Arfaoui, Kristof van Hecke, Jean-François Cavalier, Soufiane Touil. Experimental and computational investigation of Z/E isomerism, X-ray crystal structure and molecular docking study of (2-(hydroxyimino)cyclohexyl)diphenylphosphine sulfide, a potential antibacterial agent. Journal of Molecular Structure, 2020, pp.129634. ⟨10.1016/j.molstruc.2020.129634⟩. ⟨hal-03046712⟩
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