Enantioselective Synthesis of Planar Chiral Ferrocifens that Show Chiral Discrimination in Antiproliferative Activity on Breast Cancer Cells.
Chembiochem
; 21(20): 2974-2981, 2020 10 15.
Article
em En
| MEDLINE
| ID: mdl-32453493
ABSTRACT
The design and first enantioselective synthesis of a series of chiral ferrocifens and ferrociphenols was realised by enantioselective palladium-catalysed intramolecular direct C-H bond activation followed by McMurry coupling. Biological evaluation revealed moderate anticancer activities on breast cancer cells and evidence of chiral discrimination between enantiomers. Treatment of the novel ferrocifens with Ag2 O revealed that these systems are unable to form a neutral quinone methide, yet still demonstrate marked antiproliferative properties against both the hormone-dependent MCF-7 and hormone-independent MDA-MB-231 cell lines. This bioactivity arises from two mechanisms Fenton-type chemistry and the anti-estrogenic activity associated with the tamoxifen-like structure.
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MEDLINE
Assunto principal:
Neoplasias da Mama
/
Compostos Ferrosos
/
Antineoplásicos
Idioma:
En
Ano de publicação:
2020
Tipo de documento:
Article