Li Y., De Kock C., Smith P.J., Chibale K., Smith G.S.
Department of Chemistry, University of Cape Town, Rondebosch, South Africa; Department of Medicine, University of Cape Town, Groote Schuur Hospital, Observatory, South Africa; Institute of Infectious Disease and Molecular Medicine, University of Cape Town, Rondebosch, South Africa; South African Medical Research Council Drug Discovery and Development Research Unit, University of Cape Town, Rondebosch, South Africa
Li, Y., Department of Chemistry, University of Cape Town, Rondebosch, South Africa; De Kock, C., Department of Medicine, University of Cape Town, Groote Schuur Hospital, Observatory, South Africa; Smith, P.J., Department of Medicine, University of Cape Town, Groote Schuur Hospital, Observatory, South Africa; Chibale, K., Department of Chemistry, University of Cape Town, Rondebosch, South Africa, Institute of Infectious Disease and Molecular Medicine, University of Cape Town, Rondebosch, South Africa, South African Medical Research Council Drug Discovery and Development Research Unit, University of Cape Town, Rondebosch, South Africa; Smith, G.S., Department of Chemistry, University of Cape Town, Rondebosch, South Africa
A silicon-containing congener of ferroquine (1) was synthesized by incorporating an organosilicon motif in the lateral side chain of ferroquine. Compound 1 was then further reacted with dinuclear half-sandwich transition-metal precursors [Ru(Ar)(μ-Cl)Cl]2 (Ar = η6-p-iPrC6H4Me, η6-C6H6, η6-C6H5OCH2CH2OH), [Rh(COD)(μ-Cl)]2, and [RhCp∗(μ-Cl)Cl]2, to yield a series of heterometallic organometallic complexes (2-6). Compound 1 coordinates selectively in a monodentate manner to the transition metals via the quinoline nitrogen of the aminoquinoline scaffold. All of the compounds were characterized using various analytical and spectroscopic techniques, and the molecular structure of compound 1 was elucidated by single-crystal X-ray diffraction analysis. Furthermore, the in vitro antiplasmodial activity of compounds 1-6 was established against the chloroquine-sensitive (NF54) and chloroquine-resistant (Dd2) strains of the malaria parasite Plasmodium falciparum. © 2014 American Chemical Society.