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Butler W.;Kelly P.;Harry A.;Tiedt R.;White B.;Devery R.;Kenny P.
Applied Organometallic Chemistry
The synthesis, structural characterization and biological evaluation of N-(ferrocenylmethyl amino acid) fluorinated benzene-carboxamide derivatives as potential anticancer agents
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bioorganometallic chemistry breast cancer ferrocene MCF-7
A series of N-(ferrocenylmethyl amino acid) fluorinated benzene-carboxamide derivatives and have been synthesized by coupling ferrocenylmethyl amine 3 with various substituted N-(fluorobenzoyl) amino acid derivatives using the standard N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride, 1-hydroxybenzotriazole protocol. The amino acids employed in this study were glycine and L-alanine. All of the compounds were fully characterized using a combination of 1H NMR, 13C NMR, 19F NMR, distortionless enhancement by polarization transfer (DEPT)-135, 1H-1H correlation spectroscopy (COSY) and 1H-13C COSY (heteronuclear multiple-quantum correlation) spectroscopy. The compounds were biologically evaluated on the oestrogen-positive MCF-7 breast cancer cell line. Compounds, and exhibited cytotoxic effects on the MCF-7 breast cancer cell line. N-(Ferrocenylmethyl-L- alanine)-3,4,5-trifluorobenzene-carboxamide () was the most active compound, with an IC50 value of 2.84 μm. Compounds, and had lower IC 50 values than that found for the clinically employed anticancer drug cisplatin (IC50 = 16.3 μm against MCF-7). Guanine oxidation studies confirmed that was capable of generating oxidative damage via a reactive oxygen species-mediated mechanism. Copyright © 2013 John Wiley & Sons, Ltd.
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