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A series of N-(ferrocenylmethyl amino acid) fluorinated benzene-carboxamide derivatives 4b, 4c, 4d, 4e, 4f, 4g, 4h, 4i and 5b, 5c, 5d, 5e, 5f, 5g, 5h, 5i have been synthesized by coupling ferrocenylmethyl amine 3 with various substituted N-(fluorobenzoyl) amino acid derivatives using the standard N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride, 1-hydroxybenzotriazole protocol. The amino acids employed in this study were glycine and L-alanine. All of the compounds were fully characterized using a combination of 1H NMR, 13C NMR, 19F NMR, distortionless enhancement by polarization transfer (DEPT)-135, 1H–1H correlation spectroscopy (COSY) and 1H–13C COSY (heteronuclear multiple-quantum correlation) spectroscopy. The compounds were biologically evaluated on the oestrogen-positive MCF-7 breast cancer cell line. Compounds 4g, 4i, 5h and 5i exhibited cytotoxic effects on the MCF-7 breast cancer cell line. N-(Ferrocenylmethyl-L-alanine)-3,4,5-trifluorobenzene-carboxamide (5h) was the most active compound, with an IC50 value of 2.84 μm. Compounds 4i, 5h and 5i had lower IC50 values than that found for the clinically employed anticancer drug cisplatin (IC50 = 16.3 μm against MCF-7). Guanine oxidation studies confirmed that 5h was capable of generating oxidative damage via a reactive oxygen species-mediated mechanism. Copyright © 2013 John Wiley & Sons, Ltd.

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.

A series of N -(ferrocenylmethyl)benzene-carboxamide derivatives ( 4a – f ) have been synthesised by coupling ferrocenylmethyl amine 3 with benzoic acid and various substituted fluorobenzoic acids using the standard 1,3-dicyclohexylcarbodiimide (DCC), 1-hydroxybenzotriazole (HOBt) protocol. All compounds were fully characterised using a combination of 1 H NMR, 13 C NMR, 19 F NMR, DEPT-135, 1 H– 1 H COSY and 1 H– 13 C COSY (HMQC) spectroscopy and electrospray ionisation mass spectrometry (ESI-MS). The compounds 4a , 4d , 4e and 4f exhibited cytotoxic effects on the MDA-MB-435-S-F breast cancer cell line. Single crystal X-ray crystallographic data for 4d is also presented.

N-para-ferrocenyl benzoyl dipeptide esters 2–5 were prepared by coupling para-ferrocenyl benzoic acid 1 to the dipeptide ethyl esters GlyGly(OEt) 2, GlyAla(OEt) 3, GlyLeu(OEt) 4 and GlyPhe(OEt) 5. The compounds were fully characterized by a range of NMR spectroscopic techniques, mass spectrometry (ESI-MS, FABMS, MS/MS) and cyclic voltammetry (CV). The a1 and b1 ions appeared at one mass unit less than the expected mass in the tandem mass spectra. The CV curves of compounds 2–5 exhibited quasi-reversible redox behavior similar to the Fc/Fc+ redox couple and displayed oxidation potential values in the 50–55 mV range, against the Fc/Fc+ redox couple.

A series of N - para -ferrocenyl benzoyl dipeptide esters 2 – 5 were prepared by coupling para -ferrocenyl benzoic acid ( 1 ) to the dipeptide ethyl esters using the conventional 1,3-dicyclohexylcarbodiimide (DCC), 1-hydroxybenzotriazole (HOBt) protocol. The dipeptides employed in the synthesis were Ala-Gly(OEt) ( 2 ), Ala-Ala(OEt) ( 3 ), Ala-Leu(OEt) ( 4 ) and Ala-Phe(OEt) ( 5 ). The compounds were fully characterized by a range of NMR spectroscopic techniques, electrospray ionization mass spectrometry (ESI-MS) and tandem mass spectrometry (MS/MS). In addition the X-ray crystal structure of the l -alanine-glycine derivative 2 has been determined.

A series of novel N-meta-ferrocenyl benzoyl dipeptide esters (2–5) have been prepared by coupling meta-ferrocenyl benzoic acid (1) to the dipeptide ethyl esters using the conventional 1,3-dicyclohexylcarbodiimide (DCC), 1-hydroxybenzotriazole (HOBt) protocol. The dipeptides employed were GlyGly(OEt) (2), GlyAla(OEt) (3), GlyLeu(OEt) (4) and GlyPhe(OEt) (5). The compounds were fully characterized by a range of NMR spectroscopic techniques and by mass spectrometry (MALDI-MS, ESI-MS).

A series of N - ortho -ferrocenyl benzoyl amino acid ethyl esters 3 – 9 have been prepared by coupling ortho -ferrocenyl benzoic acid 2 to the amino acid ethyl esters of glycine, l -alanine, l -leucine, l -phenylalanine, β-alanine, 4-aminobutyric acid and (±)-2-aminobutyric acid using the conventional 1,3-dicyclohexylcarbodiimide, 1-hydroxybenzotriazole protocol. The compounds were fully characterized by a range of NMR spectroscopic techniques and by mass spectrometry (MALDI-MS, ESI-MS). The X-ray crystal structure of the l -phenylalanine derivative 6 has been determined.

The title compound, [Fe(C₅H₅)(C₂₁H₁₆NO)], was synthesized from the coupling reaction of anthracene-9-carboxylic acid and ferrocenylmethylamine. The ferrocenyl (Fc) group and the anthracene ring system both lie approximately orthogonal to the amide moiety. An amide-amide interaction (along the a axis) is the principal interaction [N...O = 2.910 (2) A]. A C-H...π(arene) interaction [C...centroid = 3.573 (2) A] and a C-H...O interaction [C...O = 3.275 (3) A] complete the hydrogen bonding; two short (Fc)C...C(anthracene) contacts are also present.