1,1′-Disubstituted azinylferrocenes: synthesis, antiaggregation and antioxidant activity

• Published in: Russian chemical bulletin Vol. 73; no. 8; pp. 2408 - 2421
• Main Authors: Zyryanova, E. Yu, Utepova, I. A., Musikhina, A. A., Boltneva, N. P., Kovaleva, N. V., Rudakova, E. V., Serebryakova, O. G., Makhaeva, G. F., Kiskin, M. A., Lazarev, V. F., Kuznetsova, L. S., Guzhova, I. V., Chupakhin, O. N.
• Format: Journal Article
• Language: English
• Published: New York Springer US 2024; Springer Nature B.V
• Subjects: Antioxidants; Chemistry; Chemistry and Materials Science; Chemistry/Food Science; Ferrocenes; Full Articles; Inorganic Chemistry; Organic Chemistry; Quinoline; azinylferrocenes; 2,2′-bipyridine; biological activity; butyrylcholinesterase; McMurry coupling; β-amyloid self-aggregation inhibitors; acetylcholinesterase; quinoline; ferrocene
• DOI: 10.1007/s11172-024-4364-x
• ISSN: 1066-5285

An approach to the synthesis of derivatives of unsymmetric 1,1′-disubstituted azinylferrocenes containing phenol fragments was proposed. It was found that the introduction of the quinoline or 2,2′-bipyridine moiety increases the E/Z selectivity of the reaction. The monosubstituted acetylferrocene produces the products of the pinacoline rearrangement due to the McMurry coupling, whereas only 1-azinyl-1′-{1-[(4-hydroxyphenyl)-phenylmethylene]ethyl}ferrocenes were formed in the reaction with 1-azinyl-1′-acetyl-ferrocenes. The high antioxidant activity of the synthesized compounds in the ABTS and FRAP assays and high inhibitory activity against self-aggregation of β-amyloid (1–42) was shown. Cytotoxic activity of these compounds was studied on human breast cancer cells (MCF7), non-small-cell lung cancer cells (A549), colorectal cancer cells (DLD-1), and normal dermal fibroblasts (DF-2).