N-ortho-Ferrocenyl benzoyl dipeptide esters: Synthesis, structural characterization and in vitro anti-cancer activity of N-{ortho-(ferrocenyl)benzoyl}-glycine-l-alanine ethyl ester and N-{ortho-(ferrocenyl)benzoyl}-l-alanine-glycine ethyl ester

N-ortho-ferrocenyl benzoyl dipeptide esters 2–6 were prepared by coupling ortho-ferrocenyl benzoic acid 1 to the dipeptide ethyl esters GlyGly(OEt) (2), GlyAla(OEt) (3), GlyPhe(OEt) (4), AlaGly(OEt) (5) and AlaPhe(OEt) (6). The compounds were fully characterized by a range of NMR spectroscopic techniques, mass spectrometry and cyclic voltammetry. The cytotoxicity of 3 and 5 towards lung cancer cells has been determined.

Graphical abstractN-ortho-ferrocenyl benzoyl dipeptide ethyl esters 2–6 have been prepared by coupling ortho-ferrocenyl benzoic acid to the dipeptide ethyl esters GlyGly(OEt) (2), GlyAla(OEt) (3), GlyPhe(OEt) (4), AlaGly(OEt) (5) and AlaPhe(OEt) (6) using the conventional 1,3-dicyclohexylcarbodiimide (DCC), 1-hydroxybenzatriazole (HOBt) procedure. The compounds were fully characterized by a range of NMR spectroscopic techniques, mass spectrometry and cyclic voltammetry. The IC50 values of 3 and 5 were found to be 5.3 and 21 μM, respectively, against highly invasive/super invasive lung cancer cells.Figure optionsDownload full-size imageDownload as PowerPoint slide