Synthesis, Molecular Docking, and DFT Studies of Some New 2,5-Disubstituted Benzoxazoles as Potential Antimicrobial and Cytotoxic Agents

EROL M., ÇELİK İ., UZUNHİSARCIKLI E., Kuyucuklu G.

Polycyclic Aromatic Compounds, vol.42, no.4, pp.1679-1696, 2022 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 42 Issue: 4
  • Publication Date: 2022
  • Doi Number: 10.1080/10406638.2020.1802305
  • Journal Name: Polycyclic Aromatic Compounds
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Academic Search Premier, Aerospace Database, Applied Science & Technology Source, CAB Abstracts, Chemical Abstracts Core, Communication Abstracts, Food Science & Technology Abstracts, Metadex, Pollution Abstracts, Veterinary Science Database, Civil Engineering Abstracts
  • Page Numbers: pp.1679-1696
  • Keywords: ADME prediction, antimicrobial activity, benzoxazole, cytotoxicity, molecular docking, RAPID COLORIMETRIC ASSAY, DERIVATIVES, ANTICANCER, RESISTANCE, BENZIMIDAZOLES, MECHANISMS, SURVIVAL, GROWTH
  • Kayseri University Affiliated: No

Abstract

© 2020 Taylor & Francis Group, LLC.In this study, a total of 17 piece 2,5-disubstituted benzoxazole derivatives were synthesized, 2 of which were not original, their antimicrobial activities were determined using microdilution method and their in vitro cytotoxic activities were investigated on MCF-7 and A549 cells by MTT test. When the activity results are examined, although the antibacterial effects of benzoxazole derivatives are weaker than standard drugs; 3N13 and 3N19 against Candida albicans isolate showed the closest activity to fluconazole with MIC: 16 µg/ml. The cytotoxicity test was measured at a concentration of 100 µM and a 24-h incubation period. The results showed that the compounds had weak activities against two cell lines. Molecular docking studies of synthesized compounds were performed on sterol 14α-demethylase protein (CYP51) and protein-ligand interactions of 3N13, the most effective derivative against C. albicans isolate, were showed (PDB: 5TZ1). Estimated ADME profiles of compounds were calculated and also 3N13’s were calculated HUMO-LUMO energies, molecular electrostatic potential analysis, and geometric optimization parameters with 6-311 G+ (d,p) base set using DFT/B3LYP theory, and the results were displayed.