Computational investigation and biological activity of selected Schiff bases

Segun Oladipo; Adesola A. Adeleke; Abosede A. Badeji; Katherine I. Babalola; Ayomide H. Labulo; Ibrahim Hassan; Sadiq T. Yussuf; Samuel O. Olalekan

doi:10.46481/jnsps.2024.2103

Authors

Segun Oladipo
[email protected]

Department of Chemical Sciences, Olabisi Onabanjo University, Ago-Iwoye, P.M.B. 2002, Nigeria
Adesola A. Adeleke
Department of Chemical Sciences, Olabisi Onabanjo University, Ago-Iwoye, P.M.B. 2002, Nigeria
Abosede A. Badeji
Department of Chemical Sciences, Tai Solarin University of Education, Ijagun, Ogun-State, Nigeria
Katherine I. Babalola
Department of Chemical Sciences, Olabisi Onabanjo University, Ago-Iwoye, P.M.B. 2002, Nigeria
Ayomide H. Labulo
Department of Chemistry, Federal University of Lafia, P.M.B. 146, Lafia, Nasarawa State, Nigeria
Ibrahim Hassan
Department of Chemistry, Federal University of Lafia, P.M.B. 146, Lafia, Nasarawa State, Nigeria
Sadiq T. Yussuf
Department of Chemical Sciences, Olabisi Onabanjo University, Ago-Iwoye, P.M.B. 2002, Nigeria
Samuel O. Olalekan
Department of Physiology, Olabisi Onabanjo University, Ago-Iwoye, P.M.B. 2002, Nigeria

Keywords:

Schiff base, DFT, Molecular docking, Antibacterial

Abstract

Two Schiff bases, (E)-N-(4-bromophenyl)-1-(2,6-dichlorophenyl)methanimine (S1) and (E)-4-(((4-bromophenyl)imino)methyl)phenol (S2) were synthesized and elucidated using basic spectroscopic methods such as Fourier-transform-infrared, Ultraviolet-visible as well as ¹H & ¹³C-NMR while purity of the compounds was ascertained by the means of elemental analysis. The stability, chemical reactivities and electronic properties of S1 and S2 were evaluated using Density Functional Theory (DFT). Energy band gap (?E) of S1 and S2 are 2.81 eV and 3.02 eV respectively and this inferred that S1 is more reactive as well as less stable than S2. The Molecular electrostatic potential (MEP) mapping evaluation showed that both S1 and S2 are having more of the yellow, green and red region than the blue region, signifying that these structures are prone to electrophilic attack. The compounds were screened against one Gram-negative (Staphylococcus aureus) and two Gram-positive bacteria (Klebsiella pneumoniae and Psedomonas aeruginosa) to evaluate their antibacterial potential. S1 as well as S2 showed antibacterial potential against Staphylococcus aureus and exhibited less of no activity against Klebsiella pneumoniae and Escherichia coli. In silico studies of S1 and S2 against Staphylococcus aureus was carried out and the outcomes corroborate with experimental findings. Pharmacological evaluation of S1 and S2 showed that both compounds exhibited less violation of Lipinski’s rule of five (Ro5) which pose them to be less toxic and orally available.

Dimensions

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