QIMR Berghofer

Nucleophilic substitution reactions of [(eta(5)-Cp*)Ru(eta(6)-C6H5CO2H)](+): Synthesis, characterization and cytotoxicity of organoruthenium ester and amide complexes

Abstract

This article outlines the synthesis of an electrophilic organoruthenium carboxylic acid of the structure [(eta(5)-Cp*)Ru(eta(6)-C6H5CO2H)](+) 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 [(eta(5)-Cp*) Ru(eta(6)-C6H5COOR)](+) and amide [(eta(5)-Cp*) Ru(eta(6)-C6H5CONHR)](+) or [(eta(5)-Cp*) Ru(eta(6)-C6H5CONR)](+) 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[(eta(5)-Cp*)Ru(eta(6)-C6H5CO2H)]B(C6H5)(4)center dot[(eta(5)-Cp*) Ru(eta(6)-C6H5CO2)]center dot H2O, [(eta(5)-Cp*) Ru(eta(6)-C6H5CONHCH2Ph)]PF6 and [(eta(5)-Cp*) Ru(eta(6)-C6H5CONHSO2C6H4-COMe)] PF6. 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. (C) 2016 Elsevier B.V. All rights reserved.

Authors Loughrey, Bradley T.; Williams, Michael L.; Parsons, Peter G.; Healy, Peter C.
Journal JOURNAL OF ORGANOMETALLIC CHEMISTRY
Pages 1-10
Volume 819
Date 1/09/2016
Grant ID
Funding Body Griffith University
URL http://www.ncbi.nlm.nih.gov/pubmed/?term=10.1016/j.jorganchem.2016.06.012