Synthesis, vibrational spectroscopic investigations, molecular docking, antibacterial and antimicrobial studies of 5-ethylsulphonyl-2-(p-aminophenyl)benzoxazole


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Parveen S. S. , Al-Alshaikh M. A. , Panicker C., El-Emam A. A. , ARISOY M., ARPACI Ö., ...More

Journal of Molecular Structure, vol.1115, pp.94-104, 2016 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 1115
  • Publication Date: 2016
  • Doi Number: 10.1016/j.molstruc.2016.02.057
  • Journal Name: Journal of Molecular Structure
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.94-104
  • Keywords: DFT, Benzoxazole, IR, Raman, Molecular docking, FOCAL ADHESION KINASE, TOPOISOMERASE-II INHIBITORS, AB-INITIO CALCULATIONS, FT-IR, UV INVESTIGATIONS, HETEROCYCLIC-COMPOUNDS, CHEMICAL-REACTIVITY, RAMAN, BENZOXAZOLE, H-1-NMR
  • Lokman Hekim University Affiliated: Yes

Abstract

© 2016 Elsevier B.V.The optimized molecular structure, vibrational wavenumbers, corresponding vibrational assignments of 5-ethylsulphonyl-2-(p-aminophenyl)benzoxazole have been investigated experimentally and theoretically based on density functional theory. Synthesis and antibacterial and antimicrobial activities of the title compound were reported. The FT-IR and FT-Raman spectra were recorded in solid phase and the experimental bands were assigned and characterized on the basis of potential energy distribution. The HOMO and LUMO energies show that the charge transfer occur within the molecule. Stability arising from hyperconjugative interactions and charge delocalization were analysed using natural bond orbital analysis. Binding free energy of -9.8 kcal/mol as predicted by docking studies suggests good binding affinity and the inhibitor forms a stable complex with FAK as is evident from the ligand-receptor interactions. The title compound possesses lower activity against Candida albicans with MIC value of 64 μg/ml than the compared reference drugs as fluconazole and amphotericin B and possesses the same activity with value of 64 μg/ml against Candida krusei as the reference drug, fluconazole.