Synthesis, cytotoxic and antioxidant activities of new n-substituted 3-(benzimidazol-2-yl)-chromones containing 2,6-di-tert-butylphenol fragment

• Published in: Journal of molecular structure 2022-02, Vol.1249, p.131683, Article 131683
• Main Authors: Shatokhin, Stanislav S., Tuskaev, Vladislav A., Gagieva, Svetlana Ch, Markova, Alina A., Pozdnyakov, Dmitry I., Melnikova, Elizaveta K., Bulychev, Boris M., Oganesyan, Eduard T.
• Format: Article
• Language: English
• Subjects: 3-formylchromone; Antioxidant activity; Benzimidazole; Cytotoxic activity; DFT-calculation; Drug-likeness; Sterically hindered phenols
• ISSN: 0022-2860; 1872-8014
• DOI: 10.1016/j.molstruc.2021.131683

•One-pot metal free synthesis of new hybride molecules.•9 new compounds have been synthesized and characterized.•Cytotoxicity against human colon cancer cells HCT116 and breast cancer cells MCF7.•Antioxidant activity comparable to the reference drug Trolox. The reaction of 3-formylchromones and 4-((2-aminophenyl)imino)-2,6-di‑tert-butylcyclohexa-2,5-dienone gave a series of N-substituted benzimidazole derivatives, characterized by 1H and 13C NMR spectroscopy, mass spectrometry and elemental analysis. The molecular structures of compounds 1 and 4 were determined by single crystal X-ray diffraction studies. Compounds 1–8 exhibit cytotoxic activity against human colon cancer cells HCT116 and breast cancer cells MCF7 at submicromolar concentrations. Compound 6 is more active against tumor cells than non-malignant fibroblasts. Compounds 1, 3, 5 and 7 exhibit antioxidant activity comparable to the reference drug Trolox. [Display omitted]