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

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.