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

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

“…The E 0 (oxidation potential) values for the N-(3-ferrocenyl-2-naphthoyl) derivatives 5-7 were in the range of 5-10 mV (versus Fc/Fc + ), whilst the N-(6-ferrocenyl-2-naphthoyl) derivatives 8-10 showed values in the 42-56 mV range (versus Fc/Fc + ). The values for compounds 8-10 are comparable with those reported for the N-(ferrocenyl)benzoyl dipeptide derivatives (46-59 mV versus Fc/Fc + ), which are significantly lower than ferrocenoyl dipeptide ester derivatives [20,22]. For example, Fc-Ala-Ala-OMe, was reported as E 0 ¼ 230 mV (versus Fc/Fc + ) [39].…”

“…A comprehensive review on the bioorganometallic chemistry of ferrocene has been published [6]. Examples of biologically active ferrocenyl derivatives encompass anti-bacterial [7][8][9], anti-fungal [10,11], anti-malarial [12][13][14][15] and anti-cancer therapeutic agents including ferrocifen [16][17][18][19][20][21][22][23][24][25].…”

“…Our work is focused on the synthesis of ferrocene derivatives incorporating various natural amino acids and peptide derivatives [20,22,[26][27][28][29][30][31][32][33][34][35]. In particular, several N-(ferrocenyl)benzoyl dipeptide ethyl esters have been found to possess good anti-cancer activity in vitro against the human lung carcinoma cell line H1299, the most active of which is the N-{ortho-(ferrocenyl)benzoyl}-glycine-L-alanine ethyl ester (IC 50 = 5.3 ± 0.4 lM) [20,22].…”

“…In particular, several N-(ferrocenyl)benzoyl dipeptide ethyl esters have been found to possess good anti-cancer activity in vitro against the human lung carcinoma cell line H1299, the most active of which is the N-{ortho-(ferrocenyl)benzoyl}-glycine-L-alanine ethyl ester (IC 50 = 5.3 ± 0.4 lM) [20,22].…”

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

“…Compound 5 showed an IC 50 value of 21 lM (RSD 15%), while compound 3 showed an IC 50 value of 5.3 lM (RSD 8%). N-{ortho-(ferrocenyl)-benzoyl}-glycine ethyl ester was initially tested against the above cell line and showed an IC 50 value of 48 lM (RSD 13%), while the meta analogue of 5 had an IC 50 value of 26 lM (RSD 20%) [36]. A comparison between the ortho amino acid and dipeptide compounds 3 and 5 is seen in Fig.…”