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

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dc.contributor.authorHorvath U.E.I.
dc.contributor.authorBentivoglio G.
dc.contributor.authorHummel M.
dc.contributor.authorSchottenberger H.
dc.contributor.authorWurst K.
dc.contributor.authorNell M.J.
dc.contributor.authorVan Rensburg C.E.J.
dc.contributor.authorCronje S.
dc.contributor.authorRaubenheimer H.G.
dc.contributor.authorHorvath U.E.I.
dc.contributor.authorBentivoglio G.
dc.contributor.authorHummel M.
dc.contributor.authorSchottenberger H.
dc.contributor.authorWurst K.
dc.contributor.authorNell M.J.
dc.contributor.authorVan Rensburg C.E.J.
dc.contributor.authorCronje S.
dc.contributor.authorRaubenheimer H.G.
dc.date.accessioned2011-05-15T16:05:15Z
dc.date.accessioned2011-05-15T16:05:15Z
dc.date.available2011-05-15T16:05:15Z
dc.date.available2011-05-15T16:05:15Z
dc.date.issued2008
dc.date.issued2008
dc.description.abstractThe 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.
dc.description.abstractThe 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.
dc.description.versionArticle
dc.description.versionArticle
dc.identifier.citationNew Journal of Chemistry
dc.identifier.citation32
dc.identifier.citation3
dc.identifier.citationNew Journal of Chemistry
dc.identifier.citation32
dc.identifier.citation3
dc.identifier.issn11440546
dc.identifier.issn11440546
dc.identifier.other10.1039/b713917a
dc.identifier.other10.1039/b713917a
dc.identifier.urihttp://hdl.handle.net/10019.1/13040
dc.identifier.urihttp://hdl.handle.net/10019.1/13040
dc.subjecttetrafluoroborate; imidazole derivative; unclassified drug; article; cancer cell culture; chemical reaction; chemical structure; crystal structure; cytotoxicity; hydrogen bond; priority journal; proton nuclear magnetic resonance; synthesis
dc.subjecttetrafluoroborate
dc.subjectimidazole derivative
dc.subjectunclassified drug
dc.subjectarticle
dc.subjectcancer cell culture
dc.subjectchemical reaction
dc.subjectchemical structure
dc.subjectcrystal structure
dc.subjectcytotoxicity
dc.subjecthydrogen bond
dc.subjectpriority journal
dc.subjectproton nuclear magnetic resonance
dc.subjectsynthesis
dc.titleA cytotoxic bis(carbene)gold(I) complex of ferrocenyl complexes: Synthesis and structural characterisation
dc.titleA cytotoxic bis(carbene)gold(I) complex of ferrocenyl complexes: Synthesis and structural characterisation
dc.typeArticle
dc.typeArticle
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