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

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.

Graphical abstractA series of N-meta-ferrocenyl benzoyl dipeptide esters were prepared by coupling meta-ferrocenyl benzoic acid 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), AlaAla(OEt), AlaLeu(OEt) and AlaPhe(OEt). 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.Figure optionsDownload full-size imageDownload as PowerPoint slide