Nucleophilic substitution reactions of [(η5-Cp*)Ru(η6-C6H5CO2H)]+: Synthesis, characterization and cytotoxicity of organoruthenium ester and amide complexes.

This article outlines the synthesis of an electrophilic organoruthenium carboxylic acid of the structure [(η 5 -Cp*)Ru(η 6 -C 6 H 5 CO 2 H)] + and explores the behavior of this molecule under a variety of nucleophilic substitution conditions using a range of oxygen and nitrogen based nucleophiles including alcohols, primary and secondary amines and aromatic sulfonamides. The resulting organoruthenium ester [(η 5 -Cp*)Ru(η 6 -C 6 H 5 COOR)] + and amide [(η 5 -Cp*)Ru(η 6 -C 6 H 5 CONHR)] + or [(η 5 -Cp*)Ru(η 6 -C 6 H 5 CONR)] + complexes are additionally reported. All prepared complexes have been fully characterized using Fourier-transform IR and NMR spectroscopy and electrospray mass spectrometry with single-crystal X-ray structural determinations reported for three complexes: 3[(η 5 -Cp*)Ru(η 6 -C 6 H 5 CO 2 H)]B(C 6 H 5 ) 4 .[(η 5 -Cp*)Ru(η 6 -C 6 H 5 CO 2 )].H 2 O, [(η 5 -Cp*)Ru(η 6 -C 6 H 5 CONHCH 2 Ph)]PF 6 and [(η 5 -Cp*)Ru(η 6 -C 6 H 5 CONHSO 2 C 6 H 4 COMe)]PF 6 . Complexes were also evaluated for in vitro cytotoxic activity against the MCF7 (hormone-dependant breast cancer), MDA-MD-231 (hormone-independent breast cancer), MM96L (human melanoma) tumourigenic cell lines and the normal NFF (neonatal foreskin fibroblasts) human cell line. [ABSTRACT FROM AUTHOR]