A cytotoxic bis(carbene)gold(I) complex of ferrocenyl complexes: Synthesis and structural characterisation

Date
2008, 2008
Authors
Horvath U.E.I.
Bentivoglio G.
Hummel M.
Schottenberger H.
Wurst K.
Nell M.J.
Van Rensburg C.E.J.
Cronje S.
Raubenheimer H.G.
Horvath U.E.I.
Journal Title
Journal ISSN
Volume Title
Publisher
Abstract
The N-heterocyclic carbene (NHC) precursors 1-[(E)-2-butenyl]-3-(4- ferrocenylphenyl)imidazolium bromide (2) and 1-[(E)-2-butenyl]-3-(4- ferrocenylphenyl)imidazolium tetrafluoroborate (3) were derived from 1-(4-ferrocenylphenyl)imidazole. Ferrocenyl complex 3 reacts with Ag 2O and chloro(dimethylsulfide)gold(i) in the presence of tetraethylammonium chloride to produce the mixed metal species bis{1-[(E)-2-butenyl]-3-(4-ferrocenylphenyl)-2H-imidazol-2-ylidene}gold(i) tetrafluoroborate (4). Single crystal X-ray structure analyses of 1, 3 and 4 indicate that the NCHN-hydrogen in 3 is hydrogen bonded to the BF 4- anion [C(H1)⋯F, 3.265(4) Å], as is also reflected in the position of its 1H NMR chemical shift. Cytotoxicity studies show that complex 4 is selective for cancer cells and active against the tumour cell lines Jurkat and MCF 7. © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique.
The N-heterocyclic carbene (NHC) precursors 1-[(E)-2-butenyl]-3-(4- ferrocenylphenyl)imidazolium bromide (2) and 1-[(E)-2-butenyl]-3-(4- ferrocenylphenyl)imidazolium tetrafluoroborate (3) were derived from 1-(4-ferrocenylphenyl)imidazole. Ferrocenyl complex 3 reacts with Ag 2O and chloro(dimethylsulfide)gold(i) in the presence of tetraethylammonium chloride to produce the mixed metal species bis{1-[(E)-2-butenyl]-3-(4-ferrocenylphenyl)-2H-imidazol-2-ylidene}gold(i) tetrafluoroborate (4). Single crystal X-ray structure analyses of 1, 3 and 4 indicate that the NCHN-hydrogen in 3 is hydrogen bonded to the BF 4- anion [C(H1)⋯F, 3.265(4) Å], as is also reflected in the position of its 1H NMR chemical shift. Cytotoxicity studies show that complex 4 is selective for cancer cells and active against the tumour cell lines Jurkat and MCF 7. © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique.
Description
Keywords
tetrafluoroborate; imidazole derivative; unclassified drug; article; cancer cell culture; chemical reaction; chemical structure; crystal structure; cytotoxicity; hydrogen bond; priority journal; proton nuclear magnetic resonance; synthesis, tetrafluoroborate, imidazole derivative, unclassified drug, article, cancer cell culture, chemical reaction, chemical structure, crystal structure, cytotoxicity, hydrogen bond, priority journal, proton nuclear magnetic resonance, synthesis
Citation
New Journal of Chemistry
32
3
New Journal of Chemistry
32
3