The synthesis, structural characterization and in vitro anti-cancer activity of novel 1-alkyl-10-N-para-(ferrocenyl) benzoyl dipeptide esters

摘要

1-Alkyl-10-N-para-(ferrocenyl) benzoyl dipeptide esters 4-12 were prepared by coupling the alkyl ferrocenyl benzoic acids 1-3 to the dipeptide ethyl esters Gly-L-Ala(OEt), Gly-L-Leu(OEt) and Gly-LPhe(OEt) using the standard N-(3-dimethylaminopropyl)-N'-ethylcarbodiimide hydrochloride (EDC), 1- hydroxybenzotriazole (HOBt) protocol. All the compounds were fully characterized using a combination of ~1H NMR, ~(13)C NMR, DEPT-135 and ~1He~(13)C COSY (HMQC) spectroscopy, electrospray ionization mass spectrometry (ESI-MS) and cyclic voltammetry (CV). Selected compounds showed micromolar activity in the H1299 NSCLC cell line, with IC50 values in the range of 4.5-6.6 μM.