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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-vinylfe...
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| Format: | Thesis |
| Language: | English |
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Department of Chemistry
2016
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| _version_ | 1867613414661029888 |
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| access_status_str | Open Access |
| author | Baartzes, Nadia |
| author2 | Smith, Gregory S |
| author_browse | Baartzes, Nadia Smith, Gregory S |
| author_facet | Smith, Gregory S Baartzes, Nadia |
| author_sort | Baartzes, Nadia |
| collection | Thesis |
| description | 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. |
| format | Thesis |
| id | oai:open.uct.ac.za:11427/19973 |
| institution | University of Cape Town (South Africa) |
| language | eng |
| last_indexed | 2026-06-10T12:35:46.537Z |
| license_str | Not specified — see source repository |
| provenance_str_mv | Harvested via OAI-PMH from UCTD — University of Cape Town Open Access Repository |
| publishDate | 2016 |
| publishDateRange | 2016 |
| publishDateSort | 2016 |
| publisher | Department of Chemistry |
| publisherStr | Department of Chemistry |
| record_format | dspace |
| source_str | UCTD — University of Cape Town Open Access Repository |
| spelling | oai:open.uct.ac.za:11427/19973 Mono- and polynuclear Ferrocenyl-derived complexes: synthesis, characterisation and biological evaluation as antimycobacterial and antiplasmodial agents Baartzes, Nadia Smith, Gregory S Chemistry 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. 2016-06-09T11:19:53Z 2016-06-09T11:19:53Z 2015 Master Thesis Masters MSc http://hdl.handle.net/11427/19973 eng application/pdf Department of Chemistry Faculty of Science University of Cape Town |
| spellingShingle | Chemistry Baartzes, Nadia Mono- and polynuclear Ferrocenyl-derived complexes: synthesis, characterisation and biological evaluation as antimycobacterial and antiplasmodial agents |
| thesis_degree_str | Master's |
| title | Mono- and polynuclear Ferrocenyl-derived complexes: synthesis, characterisation and biological evaluation as
antimycobacterial and antiplasmodial agents |
| title_full | Mono- and polynuclear Ferrocenyl-derived complexes: synthesis, characterisation and biological evaluation as
antimycobacterial and antiplasmodial agents |
| title_fullStr | Mono- and polynuclear Ferrocenyl-derived complexes: synthesis, characterisation and biological evaluation as
antimycobacterial and antiplasmodial agents |
| title_full_unstemmed | Mono- and polynuclear Ferrocenyl-derived complexes: synthesis, characterisation and biological evaluation as
antimycobacterial and antiplasmodial agents |
| title_short | Mono- and polynuclear Ferrocenyl-derived complexes: synthesis, characterisation and biological evaluation as
antimycobacterial and antiplasmodial agents |
| title_sort | mono and polynuclear ferrocenyl derived complexes synthesis characterisation and biological evaluation as antimycobacterial and antiplasmodial agents |
| topic | Chemistry |
| url | http://hdl.handle.net/11427/19973 |
| work_keys_str_mv | AT baartzesnadia monoandpolynuclearferrocenylderivedcomplexessynthesischaracterisationandbiologicalevaluationasantimycobacterialandantiplasmodialagents |