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The synthesis, structural characterization and in vitro anti-cancer activity of novel N-(3-ferrocenyl-2-naphthoyl) dipeptide ethyl esters and novel N-(6-ferrocenyl-2-naphthoyl) dipeptide ethyl esters by Áine Mooney; Alan J. Corry; Dermot O’Sullivan; Dilip K. Rai; Peter T.M. Kenny is a Chemistry article available to read on EtoBox.

What is The synthesis, structural characterization and in vitro anti-cancer activity of novel N-(3-ferrocenyl-2-naphthoyl) dipeptide ethyl esters and novel N-(6-ferrocenyl-2-naphthoyl) dipeptide ethyl esters about?

N-(3-ferrocenyl-2-naphthoyl) dipeptide esters (5-7) and N-(6-ferrocenyl-2-naphthoyl) dipeptide esters (8-10) were prepared by coupling either 3-ferrocenylnaphthalene-2-carboxylic acid 2 or 6-ferrocenylnaphthalene-2-carboxylic acid 4 to the dipeptide ethyl esters GlyAla(OEt) (5, 8), AlaGly(OEt) (6, 9), and AlaAla(OEt) (7, 10) using the standard N-(3-dimethylaminopropyl)-N 0 -ethylcarbodiimide hydrochloride (EDC), 1-hydroxybenzotriazole (HOBt) protocol. All the compounds were fully characterized using a combination of 1 H NMR, 13 C NMR, DEPT-135 and 1 H-13 C COSY (HMQC) spectroscopy, electrospray ionization mass spectrometry (ESI-MS) and cyclic voltammetry (CV). In vitro, the cytotoxic effects of compounds 5-10 show improvements over the corresponding N-(ferrocenyl)benzoyl derivatives, with IC 50 values against the H1299 lung cancer cells ranging from 1.2 lM to 8.0 lM. N-(6-ferrocenyl-2-naphthoyl)-glycine-L-alanine ethyl ester 8 was found to be the most active derivative of the naphthoyl series so far, displaying an IC 50 value of 1.3 ± 0.1 lM. This value is slightly lower than that found for the clinically employed anti-cancer drug cisplatin (IC 50 = 1.5 ± 0.1 lM against H1299).

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Author

Áine Mooney; Alan J. Corry; Dermot O’Sullivan; Dilip K. Rai; Peter T.M. Kenny

Publisher

Elsevier Science; Elsevier ; Elsevier BV (ISSN 0022-328X)

Published

2009

Language

EN

Field

Chemistry (Physical Sciences)