A new approach for the synthesis of new benzothiazole derivatives and their biological and docking evaluation | ||||
| Mansoura Journal of Chemistry | ||||
| Volume 62, Issue 4, August 2023, Page 39-55 PDF (1.74 MB) | ||||
| Document Type: Original Article | ||||
| DOI: 10.21608/mjcc.2023.411561 | ||||
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| Authors | ||||
| Mina Nader* 1; Ehab Abdel-Latif1; Ahmed A. Fadda1; Nanees N. Soliman1; Yasmin Tag2 | ||||
| 1Department of Chemistry, Faculty of Science, Mansoura University, Egypt | ||||
| 2Oral Biology Department, Faculty of Oral and Dental Medicine, Delta University for Science and Technology, Mansoura, Egypt | ||||
| Abstract | ||||
| Here, we describe how hydrazonoyl malononitrile compound 2 reacts with a variety of secondary amines in boiling ethanol to synthesis the corresponding acrylonitrile compounds 3–8. Additionally, compound 2 produced the pyrazole derivative 9 and the pyridazine derivative 11, respectively, through reactions with hydrazine hydrate and malononitrile. Additionally, in a boiling solution of ethanolic sodium ethoxide, malononitrile and 7 reacted to form pyrimidine 14. N-Acetylpentaacetate 15 was produced by heating 7 in boiling acetic anhydride, and N-acetyl-2-pyridone 16 was formed by prolonged heating in DMF with catalytic amounts of TEA. In addition, when compound 7 and triethyl orthoformate were reacted with "acetic anhydride", the resulting "ethoxymethyleneamino" 17 was produced. By refluxing a solution of compound 7 and DMF/DMA in dry xylene, dimethyl formimidamide 18 was produced. The phthalimide derivatives 19–26 were formed by refluxing acid anhydride derivatives with compound 7 in DMF and acetic acid. Compounds 7 and 8 have been determined to have the strongest antioxidant activity. The effectiveness of the newly synthesized compounds 3, 4, 7, 8, 9, 11, 14–18, and 19–26 was evaluated for their antitumor activities against four cell lines; HepG2, WI–38, VERO, and MCF-7. Additionally, it was found that the two drugs, 14, and 20, exhibit potent efficacy against the four cell lines tested. Molecular docking (PDB=1M17) was used to examine the binding disposition of the docked compounds, in particular 7, 8, 11, and 14, towards the binding site of the EGFR complexed with the co-crystallized ligand | ||||
| Keywords | ||||
| Enaminonitrile; Pyrazole; Pyrimidine; Pyridine; Malononitrile; N-methyl glucamine | ||||
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