Akademik Veri Yönetim Sistemi
Chemical Papers, cilt.77, sa.11, ss.6829-6847, 2023 (SCI-Expanded)
In this study, a benzidine-based azomethine derivate 2 with a proposed new mechanism and its two derivatives 4a-b have been designed, synthesized and characterized by 1H, 13C NMR, FT-IR, and HRMS spectroscopic techniques, and their anticancer properties were investigated. The target compounds 2, 4a-b were obtained with excellent yields (91% and above) by condensation of benzidine (1) with three different aldehyde derivatives (formaldehyde, benzaldehyde 3a or p-nitrobenzaldehyde 3b) in refluxing EtOH. Surprisingly, treatment of benzidine (1) with formaldehyde afforded N 4,N 4,N 4',N 4'-tetrakis(ethoxymethyl)-[1,1'-biphenyl]-4,4'-diamine (2). The anticancer properties of these benzidine derivatives 2, 4a-b against two cell lines (MDA-MB-231 human breast adenocarcinoma and DLD1 human colorectal adenocarcinoma cell lines) were investigated with a colorimetric assay using the tetrazolium salt WST-8 (2-(2-methoxy-4-nitrophenyl)-3-(4-nitrophenyl)-5-(2,4-disulfophenyl)-2H-tetrazolium, monosodium salts). The obtained results showed that the benzidine-based azomethine derivatives 2, 4a-b had a significant effect on the human breast cancer cell line (MDA-MB-231). Then, molecular docking calculations were made to compare the biological activities of benzidine-based azomethine derivatives 2, 4a-b against cancer proteins. ADME/T analysis was performed to examine the drug properties of benzidine-based azomethine derivatives 2, 4a-b. The compounds 2, 4a-b are promising as potential anticancer drug candidates. Graphical Abstract: [Figure not available: see fulltext.]