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, cilt.42, sa.4, ss.1679-1696, 2022 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 42 Sayı: 4
  • Basım Tarihi: 2022
  • Doi Numarası: 10.1080/10406638.2020.1802305
  • Dergi Adı: POLYCYCLIC AROMATIC COMPOUNDS
  • Derginin Tarandığı İndeksler: 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
  • Sayfa Sayıları: ss.1679-1696
  • Anahtar Kelimeler: ADME prediction, antimicrobial activity, benzoxazole, cytotoxicity, molecular docking
  • Erciyes Üniversitesi Adresli: Evet

Özet

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 theirin vitrocytotoxic 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;3N13and3N19againstCandida albicansisolate showed the closest activity to fluconazole with MIC: 16 mu g/ml. The cytotoxicity test was measured at a concentration of 100 mu M 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 14 alpha-demethylase protein (CYP51) and protein-ligand interactions of3N13, the most effective derivative againstC. albicansisolate, were showed (PDB: 5TZ1). Estimated ADME profiles of compounds were calculated and also3N13'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.