Investigation of structural, spectral, electronic, and biological properties of 1,3-disubstituted benzimidazole derivatives

• Published in: Journal of molecular structure Vol. 1219; p. 128582
• Main Authors: Akkoç, Senem, Tüzün, Burak, İlhan, İlhan Özer, Akkurt, Mehmet
• Format: Journal Article
• Language: English
• Published: Elsevier B.V 05-11-2020
• Subjects: Benzimidazolium salt; DFT; Molecular docking; Spectroscopic properties; X-ray; Spectroscopic properties; DFT; X-ray; Benzimidazolium salt; Molecular docking
• ISSN: 0022-2860; 1872-8014
• DOI: 10.1016/j.molstruc.2020.128582

This article reports studies on benzimidazole based heterocyclic compounds (S3-S5). X-ray diffraction technique was applied to study the structure of (C23H19N4O2)+.Br−.H2O, namely 1-[(2-cyanophenyl)methyl]-3-[2-(4-nitrophenyl)ethyl]-1H-benzimidazol-3-ium bromide monohydrate (S3). The molecules are linked by C—H⋯Br hydrogen bonds in the crystal and there are π-π stacking interactions between the centroids of the benzene ring in the benzimidazole nucleus. The theoretical, and chemical data of S3-S5 were compared with experimental calculations via NMR, IR, and UV–Vis spectra of the molecules. Afterwards, the biological activities of the molecules were compared against colon cancer antigen proteins, ID 2HQ6, and a breast cancer protein, which is a crystal structure of a dimeric caspase-9, ID 2AR9. Experimental and theoretical studies have shown that the biological activity of the molecule S5 is higher than that of other molecules.
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•A compound was characterized by X-ray diffraction method.•The theoretical data of molecules were compared with experimental results.