Synthesis, biological evaluation, molecular docking, and acid dissociation constant of new bis-1,2,3-triazole compounds
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In this study, new bis-1,2,3-triazole derivatives, N,N′-(1,3-phenylene)bis(2-(4-R-1H-1,2,3-triazol-1-yl)acetamide), were synthesized by copper-catalyzed azide-alkyne cycloaddition click chemistry in 84–96 % yield. A wide range bioactivity screening was performed to determine DNA cleavage, antioxidant, antibacterial and antifungal activities. All of the synthesized bis-1,2,3-triazoles showed excellent DNA cleavage activity and 4 e, bearing 2-bromoethyl moiety as a substituent, was almost degraded all of the plasmid DNA. Molecular docking simulations suggest that the synthesized compounds act as minor groove binders of DNA. The antioxidant activities of the bis-1,2,3-triazoles were determined based on the radical scavenging effect of the stable 2,2-diphenyl-1-picrylhydrazyl (DPPH) free radical and iron chelating activity. The compounds exhibited effective iron chelating activity at 200 mg/L while showing a moderate ability to scavenge DPPH radical. The compounds exhibited antibacterial activity against B. cereus, L. pneumophila subsp. pneumophila, S. aureus, P. aeruginosa, E. coli and E. hirae bacterial strains, and antifungal activity against C. albicans and C. tropicalis microfungus strains with a MIC value in the range of 4–128 μg/mL. 4 d, bearing cyclohexylmethyl moiety as substituent, exhibited a broad-spectrum antimicrobial activity (both antibacterial and antifungal). Four different acid dissociation constant (pKa) values of each product were determined potentiometrically in 20 % (v/v) dimethyl sulfoxide-water at 25±0.1 °C, at an ionic background of 0.1mol/L of NaCl using the HYPERQUAD program.
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