Dual inhibition of S. aureus TyrRS and S. aureus gyrase by two 4-amino-4′-acetyldiphenyl sulfide-based Schiff bases: Structural features, DFT study, Hirshfeld surface analysis and molecular docking

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dc.contributor.authorSoumia Kadri
dc.contributor.authorAmani Direm
dc.contributor.authorAthmani Hamza
dc.contributor.authorBrahim El Bali
dc.contributor.authorCemal Parlak
dc.contributor.authorRabihe Hebbachi
dc.date.accessioned2024-02-14T12:30:16Z
dc.date.available2024-02-14T12:30:16Z
dc.date.issued2022
dc.description.abstractTwo 4-amino-4′ -acetyldiphenyl sulfide-based Schiff bases, namely 1-[4-({4-[(E)-(2hydroxynaphthalen-1-yl) methylideneamino]phenyl}sulfanyl)-phenyl]ethanone (I) and (E)-1-[4-({4-[(4methoxybenzylidene)amino] phenyl}-sulfanyl)phenyl]ethan-1-one (II) were structurally studied. They crystallize respectively in the monoclinic Cc and the triclinic P1 space groups, with the respective cell parameters: [10.695(3) Å, 44.458(14) Å, 4.4437(11) Å, 99.004(9)°] and [5.7708(2) Å, 8.0867(3) Å, 19.6929(8) Å, 81.844(2)◦, 86.664(3)◦, 85.662(3)◦]. The asymmetric units of (I) and (II) are composed of one molecule and two crystallographically independent molecules, respectively. Their molecular structures were optimized by the density functional theory and correlated correspondingly to the crystal structures. Moreover, the IR vibration modes were assigned to the calculate wavenumbers, the Mulliken atomic charges obtained and the frontier molecular orbitals evaluated. The hydrogen bonding and the non-classical intermolecular interactions within the two frameworks were investigated using Hirshfeld surface analysis which indicated the presence of C–H…H–C, C–H⋅⋅⋅π, C–H⋅⋅⋅O, C–H⋅⋅⋅N, C–H⋅⋅⋅S and π⋅⋅⋅lp interactions as well as π⋅⋅⋅π stacking. Additionally, in order to understand the interacting binding sites of the two molecules with the bacterial S. aureus protein receptors, the studied compounds were in silico eval- uated by molecular docking against tyrosyl-tRNA synthetase 1JIJ and topoisomerase II DNA gyrase 2XCT en- zymes. The results revealed consequently potent antimicrobial efficacy through the formed hydrogen bonds, hydrophobic contacts, π-cation interactions and π…π stacking.
dc.identifier.urihttp://dspace.univ-khenchela.dz:4000/handle/123456789/922
dc.language.isoen
dc.publisherInorganic Chemistry Communications 143 (2022) 109779
dc.titleDual inhibition of S. aureus TyrRS and S. aureus gyrase by two 4-amino-4′-acetyldiphenyl sulfide-based Schiff bases: Structural features, DFT study, Hirshfeld surface analysis and molecular docking
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