Synthesis, structure and cytotoxicity of triphenylphosphinegold(I) sulfanylpropenoates

The reaction of triphenylphosphinegold(I) chloride in ethanol in a 1:1 molar ratio with the 3-(aryl)-2-sulfanylpropenoic acids H(2)xspa [x: p = 3-phenyl-, Clp = 3-(2-chlorophenyl)-, -o-mp = 3-(2-methoxyphenyl)-, -p-mp = 3-(4-methoxyphenyl)-, -o-hp = 3-(2-hydroxyphenyl)-, -p-hp = 3-(4-hydroxyphenyl)-, diBr-o-hp = 3-(3,5-dibromo-2-hydroxyphenyl)-, f = 3-(2-furyl)-, t = 3-(2-thienyl)-, -o-py = 3-(2-pyridyl)-; spa = 2-sulfanylpropenoato] gave compounds of the type [Au(PPh3)(Hxspa)], which were isolated and characterized as solids by elemental analysis, IR spectroscopy and FAB mass spectrometry and in solution by H-1, C-13 and P-31 NMR spectroscopy. The structures of the complexes [Au(PPh3)(HClpspa)], [Au(PPh3)(H-o-mpspa)] and [Au(PPh3)(H-p-mpspa)] center dot 2/3C(3)H(6)O were determined by X-ray diffractometry. Hydrogen bonding was found along with Au-S and Au-P bonds in all cases and weak pi-pi stacking was found in the H-p-mpspa derivative. The in vitro antitumour activities against the HeLa-229, A2780 and A2780cis cell lines were determined for all complexes. (c) 2007 Elsevier Inc. All rights reserved.