Synthesis, Molecular Docking, and DFT Studies of Some New 2, 5-Disubstituted Benzoxazoles as Potential Antimicrobial and Cytotoxic Agents. (21st April 2022)

• Record Type: Journal Article
• Authors: Erol, Meryem; Celik, Ismail; Uzunhisarcikli, Ebru; Kuyucuklu, Gulcan
• Is Part Of: Polycyclic aromatic compounds. Volume 42:Number 4(2022)
• Page Start: 1679
• Page End: 1696
• Publication Date: 2022-04-21
• Subjects: ADME prediction -- antimicrobial activity -- benzoxazole -- cytotoxicity -- molecular docking; Polycyclic aromatic compounds -- Periodicals; 547
• DOI: 10.1080/10406638.2020.1802305
• Languages: English
• ISSNs: 1040-6638

Abstract

Abstract: 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.