Ferrocenyl catechols : synthesis, oxidation chemistry and anti-proliferative effects on MDA-MB-231 breast cancer cells
Tan, Kelvin Yong Leng
Hillard, Elizabeth A.
Leong, Weng Kee
Date of Issue2012
School of Physical and Mathematical Sciences
The synthesis and anti-tumoral properties of a series of compounds possessing a ferrocenyl group tethered to a catechol via a conjugated system is presented. On MDA-MB-231 breast cancer cell lines, the catechol compounds display a similar or greater anti-proliferative potency (IC50 values ranging from 0.48–1.21 μM) than their corresponding phenolic analogues (0.57–12.7 μM), with the highest activity found for species incorporating the ferrocenophane motif. On the electrochemical timescale, phenolic compounds appear to oxidize to the quinone methide, while catechol moieties form the o-quinone by a similar mechanism. Chemical oxidation of selected compounds with Ag2O confirms this interpretation and demonstrates the probable involvement of such oxidative metabolites in the in vitro activity of these species.
© 2012 The Royal Society of Chemistry.