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- Title
The synthesis, structural characterization and biological evaluation of N-(ferrocenylmethyl amino acid) fluorinated benzene-carboxamide derivatives as potential anticancer agents.
- Authors
Butler, William E.; Kelly, Paula N.; Harry, Andy G.; Tiedt, Rachel; White, Blanaid; Devery, Rosaleen; Kenny, Peter T. M.
- Abstract
A series of N-(ferrocenylmethyl amino acid) fluorinated benzene-carboxamide derivatives 4b 4c 4d 4e 4f 4g 4h 4i and 5b 5c 5d 5e 5f 5g 5h 5i 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 . 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 4g, 4i, 5h and 5i exhibited cytotoxic effects on the MCF-7 breast cancer cell line. N-(Ferrocenylmethyl-L-alanine)-3,4,5-trifluorobenzene-carboxamide ( 5h) was the most active compound, with an IC50 value of 2.84 μ m. Compounds 4i, 5h and 5i had lower IC50 values than that found for the clinically employed anticancer drug cisplatin (IC50 = 16.3 μ m against MCF-7). Guanine oxidation studies confirmed that 5h was capable of generating oxidative damage via a reactive oxygen species-mediated mechanism. Copyright © 2013 John Wiley & Sons, Ltd.
- Publication
Applied Organometallic Chemistry, 2013, Vol 27, Issue 6, p361
- ISSN
0268-2605
- Publication type
Article
- DOI
10.1002/aoc.2994