Enantioselective Synthesis of Planar Chiral Ferrocifens that Show Chiral Discrimination in Antiproliferative Activity on Breast Cancer Cells | Zendy

Cunningham Laura | Zendy; Wang Yong | Zendy; Nottingham Chris | Zendy; Pagsulingan Jammah | Zendy; Jaouen Gérard | Zendy; McGlinchey Michael J. | Zendy; Guiry Patrick J. | Zendy

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Enantioselective Synthesis of Planar Chiral Ferrocifens that Show Chiral Discrimination in Antiproliferative Activity on Breast Cancer Cells

Author(s) -

Cunningham Laura,

Wang Yong,

Nottingham Chris,

Pagsulingan Jammah,

Jaouen Gérard,

McGlinchey Michael J.,

Guiry Patrick J.

Publication year - 2020

Publication title -

chembiochem

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.05

H-Index - 126

eISSN - 1439-7633

pISSN - 1439-4227

DOI - 10.1002/cbic.202000311

Subject(s) - enantioselective synthesis , quinone methide , tamoxifen , enantiomer , intramolecular force , chemistry , stereochemistry , cancer cell , combinatorial chemistry , breast cancer , quinone , catalysis , biochemistry , cancer , medicine

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 Ag 2 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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