| Yazarlar |
Musa Erdoğan
Kafkas Üniversitesi, Turkey |
|
Ali Yeşildağ
Kafkas Üniversitesi, Turkey |
|
Barış Yıldız
Kafkas Üniversitesi, Turkey |
|
Burak Tüzün
Cumhuriyet Üniversitesi, Turkey |
|
Özkan Özden
Kafkas Üniversitesi, Turkey |
| Özet |
| 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.] |
| Anahtar Kelimeler |
| ADME/T | Anticancer activities | Azomethine derivatives | DLD1 | MDA-MB-231 | Molecular docking |
| Makale Türü | Özgün Makale |
| Makale Alt Türü | SSCI, AHCI, SCI, SCI-Exp dergilerinde yayımlanan tam makale |
| Dergi Adı | Chemical Papers |
| Dergi ISSN | 0366-6352 |
| Dergi Tarandığı Indeksler | SCI-Expanded |
| Dergi Grubu | Q3 |
| Makale Dili | Türkçe |
| Basım Tarihi | 07-2023 |
| Cilt No | 77 |
| Sayı | 11 |
| Sayfalar | 6829 / 6847 |
| Doi Numarası | 10.1007/s11696-023-02981-3 |
| Makale Linki | http://dx.doi.org/10.1007/s11696-023-02981-3 |
| Atıf Sayıları | |
| SCOPUS | 4 |
| Google Scholar | 10 |
