Journal
CHEMBIOCHEM
Volume 21, Issue 20, Pages 2974-2981Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/cbic.202000311
Keywords
anti-tumor agents; bio-organometallics; chirality; enantioselective synthesis; ferrocifen
Funding
- Synthesis and Solid State Pharmaceutical Centre - Science Foundation Ireland (SFI) [12\RC\2275]
- European Regional Development Fund [14/SP/2750]
- Irish Research Council (IRC) [GOIPG/2017/390, RS/2012/607]
- Higher Education Authority's PRTLI
- Feroscan
- PSL
- Irish Research Council (IRC) [GOIPG/2017/390] Funding Source: Irish Research Council (IRC)
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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 Ag2O 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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