Mono- and polynuclear Ferrocenyl-derived complexes: synthesis, characterisation and biological evaluation as antimycobacterial and antiplasmodial agents

Ferrocene-containing precursors, vinylferrocene and (E)-4-vinylferrocenylbenzaldehyde were prepared, by a Wittig olefination reaction and Heck cross-coupling reaction, respectively. Mononuclear ferrocenyl-derived imino complexes were synthesised by Schiff-base condensation reactions of (E)-4-vinylferrocenylbenzaldehyde with various amines. This included the preparation of a silicon-containing derivative and its carbon analogue, to determine the effect of the lipophilic moiety on the biological activity. In addition, polynuclear ferrocenyl-derived imino complexes based on the tris(2-aminoethyl)amine scaffold and the polypropyleneimine (PPI) first- and second-generation scaffolds were also synthesised using Schiff-base chemistry. These polynuclear complexes were prepared using template chemical procedures to that of the mononuclear complexes. The corresponding mono- and polynuclear ferrocenyl-derived amino complexes were synthesised via reductive amination reactions from the (E)-4-vinylferrocenylbenzaldehyde. The imine moiety was hydrogenated in order to compare the effect on the biological activity. The imino and amino complexes were isolated in moderate to high yields. A second series of ferrocenyl complexes was also prepared incorporating a thiosemicarbazone moiety, as this is a known pharmacophore and may confer favourable properties in terms of biological activity as well as solubility. Methyl hydrazinecarbodithioate was synthesised and reacted with the previously synthesised (E)-4-vinylferrocenylbenzaldehyde by a Schiff-base condensation reaction to afford a ferrocenyl dithiocarbamate. The dithiocarbamate was reacted with various amines via nucleophilic substitution reactions to give mono- and polynuclear ferrocenylthiosemicarbazone complexes. These complexes were isolated in low to moderate yields.

Grantor dc:publisher.institution

Department of Chemistry

Year dc:date.issued

2015

Author dc:creator

• Baartzes, Nadia

Advisor dc:contributor.advisor

• Smith, Gregory S

Language dc:language.iso

eng

Handle dc:identifier.uri

http://hdl.handle.net/11427/19973

OAI identifier oai:identifier

oai:open.uct.ac.za:11427/19973