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The synthesis and structural characterization of novel N-meta-ferrocenyl benzoyl dipeptide esters: The X-ray crystal structure and in vitro anti-cancer activity of N-{meta-ferrocenyl)benzoyl}-l-alanine-glycine ethyl ester |
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| Authors: | Alok Goel,David Savage,Paula N. Kelly,Dermot O&rsquo Sullivan,Peter T.M. Kenny |
| Affiliation: | a School of Chemical Sciences, Dublin City University, Glasnevin, Dublin 9, Ireland b National Institute for Cellular Biotechnology, Dublin City University, Glasnevin, Dublin 9, Ireland c Department of Chemistry, University College Dublin, Belfield, Dublin 4, Ireland |
| Abstract: | A series of N-meta-ferrocenyl benzoyl dipeptide esters 2-5 have been prepared by coupling meta-ferrocenyl benzoic acid 1b to the dipeptide ethyl esters using the conventional 1,3-dicyclohexylcarbodiimide (DCC), 1-hydroxybenzotriazole (HOBt) protocol. The dipeptides employed in the synthesis were AlaGly(OEt) (2), AlaAla(OEt) (3), AlaLeu(OEt) (4) and AlaPhe(OEt) (5). The compounds were fully characterized by a range of NMR spectroscopic techniques, mass spectrometry (MALDI-MS, ESI-MS), and cyclic voltammetry (CV). In addition, the X-ray crystal structure and cytotoxicity of N-{meta-(ferrocenyl)-benzoyl}-l-alanine-glycine ethyl ester (2) towards lung cancer cells has been determined. |
| Keywords: | Ferrocene Bioorganometallic chemistry ESI CV Dipeptides X-ray Cytotoxicity Lung cancer |
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