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Synthesis, structural characterisation and biological activity of novel N-(ferrocenylmethyl)benzene-carboxamide derivatives |
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| Authors: | Paula N. Kelly,Adeline Prê tre,Isobel O&rsquo Rielly,Rosaleen Devery,Alok Goel,John F. Gallagher,Peter T.M. Kenny |
| Affiliation: | a National Institute for Cellular Biotechnology, DCU, Dublin 9, Ireland b School of Chemical Sciences, Dublin City University, Dublin 9, Ireland c University of Nantes, Nantes, France d School of Biotechnology, DCU, Dublin 9, Ireland e Department of Chemistry, 80 St. George St., University of Toronto, Ont., Canada M5S 3H6 |
| Abstract: | 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. |
| Keywords: | Ferrocene Bioorganometallic chemistry Breast cancer MDA-MB-435-S-F X-ray crystal structure |
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