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Synthesis, structural characterisation and biological activity of novel N-(ferrocenylmethyl)benzene-carboxamide derivatives

2006; Elsevier BV; Volume: 692; Issue: 6 Linguagem: Inglês

10.1016/j.jorganchem.2006.11.012

1872-8561

Paula N. Kelly, Adeline Prêtre, Siobhan Devoy, Isobel O’Rielly, Rosaleen Devery, Alok Goel, John F. Gallagher, Alan J. Lough, Peter T.M. Kenny,

Synthesis and Biological Evaluation

A series of N-(ferrocenylmethyl)benzene-carboxamide derivatives (4a–f) have been synthesised by coupling ferrocenylmethyl amine 3 with benzoic acid and various substituted fluorobenzoic acids using the standard 1,3-dicyclohexylcarbodiimide (DCC), 1-hydroxybenzotriazole (HOBt) protocol. All compounds were fully characterised using a combination of 1H NMR, 13C NMR, 19F NMR, DEPT-135, 1H–1H COSY and 1H–13C COSY (HMQC) spectroscopy and electrospray ionisation mass spectrometry (ESI-MS). The compounds 4a, 4d, 4e and 4f exhibited cytotoxic effects on the MDA-MB-435-S-F breast cancer cell line. Single crystal X-ray crystallographic data for 4d is also presented.