1,1′-Disubstituted azinylferrocenes: synthesis, antiaggregation and antioxidant activity
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 pr...
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Published in | Russian chemical bulletin Vol. 73; no. 8; pp. 2408 - 2421 |
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Main Authors | , , , , , , , , , , , , |
Format | Journal Article |
Language | English |
Published |
New York
Springer US
2024
Springer Nature B.V |
Subjects | |
Online Access | Get full text |
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Summary: | 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). |
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ISSN: | 1066-5285 1573-9171 |
DOI: | 10.1007/s11172-024-4364-x |