Synthesis, quantum mechanical calculations, antimicrobial activities and molecular docking studies of five novel 2,5-disubstituted benzoxazole derivatives

ARPACI Ö., Zeyrek C. T., ARISOY M., EROL M., Celik I., Kaynak-Onurdag F.

Journal of Molecular Structure, vol.1245, 2021 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 1245
  • Publication Date: 2021
  • Doi Number: 10.1016/j.molstruc.2021.131084
  • Journal Name: Journal of Molecular Structure
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Academic Search Premier, Chemical Abstracts Core, INSPEC
  • Keywords: ADME prediction, Antimicrobial activity, Benzoxazole, Density functional theory, Molecular docking, BIOLOGICAL EVALUATION, ANTICANCER, BENZIMIDAZOLES, BINDING
  • Lokman Hekim University Affiliated: Yes


© 2021 Elsevier B.V.In this study, five new 2-(p-(Substituted)phenyl)-5-(3-(4-ethylpiperazine-1-yl) propionamido)benzoxazole derivatives (B7-B11) were designed, synthesized, and their antimicrobial activities were determined by the microdilution method. The novel benzoxazole compounds were characterized using FTIR, 1H NMR, and 13C NMR spectroscopy, mass spectroscopy, and elemental analysis. B7 and B11 showed promising activity against P. aeruginosa isolate at 16 µg/mL compared to the reference drugs. Quantum mechanical calculations were performed on five compounds in the ground state using density functional theory (DFT) with the B3LYP/6–311G(d,p) level. Molecular docking studies of the compounds were also performed a complex structure of the DNA gyrase enzyme with ciprofloxacin (PDB: 2XCT), and it was observed that the binding poses were similar to ciprofloxacin. Theoretical ADME profiles of the compounds conform to Lipinski and other limiting rules.