{"id":{"repo_id":"cape-town","oai_identifier":"oai:open.uct.ac.za:11427/16003"},"canonical_url":"https://search.dev.ndltd.org/etd/cape-town/oai:open.uct.ac.za:11427/16003","repository":{"repo_id":"cape-town","name":"University of Cape Town","base_url":"https://open.uct.ac.za/oai/request"},"display":{"title":"Syntheses of novel acyclic amino-amido ligands","abstract":"Towards the labelling of biological macromolecules in contrast media, a synthesis of the novel bifunctional amido-ligands N,N' -bis[2-(N'',N''-dimethylamino)ethyl]-4-aminobenzylmalondiamide (67) and the 3-aminopropyl derivative (66) from appropriately C-functionalized malonates by amidation with N,N-dimethylethylenediamine (62) followed by reduction of the respective nitro (64) and cyano (63) groups is described. The synthesis of N,N'-bis[2-(N'',N''-dimethylamino)ethyl]iminodiacetamide (73) from diethyl N-benzyliminodiacetate (79) by amidation· with (62) followed by debenzylation is described. Herein is also reported the unsuccessful attempts to prepare a functionalized pentaamine ligand similar to (73) via the intermediacy of N,N'-bis[2-(N'',N''-dimethylamino)ethyl]-N'''-(2,2-diethoxyethyl) iminodiacetamide (112) whose preparation is also detailed. Attempts to this end via the Mitsunobu and Steglich coupling of N,N' -bis[2-(N'',N''- dimethylamino)ethyl]-N'''-(2-hydroxyethyl)iminodiacetamide (100) with N-tertbutyloxycarbonylglycine (105) also met with failure .. Further failed attempts to secure suitably functionalized intermediates by N-alkylation of diethyl iininodiacetate (70) with appropriate electrophiles are described. The successful functionalization of the pentaamine series of ligands by N-alkylation of (73) withpnitrobenzoyl chloride (118) to give N,N' -bis[2-(N'',N''- dimethylamino)ethyl] N''' -(4-nitrobenzamido)iminodiacetamide (119) is presented. The preparation of the non-functionalized novel trioxo heptaamine ligand N,N' ,N''-tris[2-(N'',N''-dimethylamino)ethyl]nitrilotriacetamide hydrochloride (86a) is also described. An investigative study towards the assembly of a novel triamine system for encapsulating NMR or isotopic NMR-active metal ions for possible use in diagnostic medicine is reported. The key facet to this end is the reported preparation of N,N' ,N''-tris(2-aminoethyl)propane-1,2,3-tricarboxamide (89) by controlled amidation of trimethyl propane 1,2,3-tricarboxylate (88) with ethylenediamine. The syntheses of functionalized and non-functionalized novel tetraamine dioxo and trioxo ligands from glycine, ethyl N-benzylglycinate (78), L-valine, and L-lysine via classical peptide synthesis methodology (in part) are described.","abstract_html":"Towards the labelling of biological macromolecules in contrast media, a synthesis of the novel bifunctional amido-ligands N,N' -bis[2-(N'',N''-dimethylamino)ethyl]-4-aminobenzylmalondiamide (67) and the 3-aminopropyl derivative (66) from appropriately C-functionalized malonates by amidation with N,N-dimethylethylenediamine (62) followed by reduction of the respective nitro (64) and cyano (63) groups is described. The synthesis of N,N'-bis[2-(N'',N''-dimethylamino)ethyl]iminodiacetamide (73) from diethyl N-benzyliminodiacetate (79) by amidation· with (62) followed by debenzylation is described. Herein is also reported the unsuccessful attempts to prepare a functionalized pentaamine ligand similar to (73) via the intermediacy of N,N'-bis[2-(N'',N''-dimethylamino)ethyl]-N'''-(2,2-diethoxyethyl) iminodiacetamide (112) whose preparation is also detailed. Attempts to this end via the Mitsunobu and Steglich coupling of N,N' -bis[2-(N'',N''- dimethylamino)ethyl]-N'''-(2-hydroxyethyl)iminodiacetamide (100) with N-tertbutyloxycarbonylglycine (105) also met with failure .. Further failed attempts to secure suitably functionalized intermediates by N-alkylation of diethyl iininodiacetate (70) with appropriate electrophiles are described. The successful functionalization of the pentaamine series of ligands by N-alkylation of (73) withpnitrobenzoyl chloride (118) to give N,N' -bis[2-(N'',N''- dimethylamino)ethyl] N''' -(4-nitrobenzamido)iminodiacetamide (119) is presented. The preparation of the non-functionalized novel trioxo heptaamine ligand N,N' ,N''-tris[2-(N'',N''-dimethylamino)ethyl]nitrilotriacetamide hydrochloride (86a) is also described. An investigative study towards the assembly of a novel triamine system for encapsulating NMR or isotopic NMR-active metal ions for possible use in diagnostic medicine is reported. The key facet to this end is the reported preparation of N,N' ,N''-tris(2-aminoethyl)propane-1,2,3-tricarboxamide (89) by controlled amidation of trimethyl propane 1,2,3-tricarboxylate (88) with ethylenediamine. The syntheses of functionalized and non-functionalized novel tetraamine dioxo and trioxo ligands from glycine, ethyl N-benzylglycinate (78), L-valine, and L-lysine via classical peptide synthesis methodology (in part) are described.","abstract_has_math":false,"creators":["Msimang, Nkosinathi Lorenzo"],"institution":"Department of Chemistry","degree_name":null,"degree_level":null,"degree_discipline":null,"degree_department":null,"school":null,"contributors":[],"advisors":["Elsworth, J F","Jackson, Graham Ellis"],"committee_chairs":[],"committee_members":[],"year":1990,"date_issued":"1990","date_published":"1990","updated_at":"2026-07-24T01:33:54Z","subjects":[],"languages":["eng"],"rights":[],"rights_urls":[],"identifier_entries":[]},"links":{"outbound_url":"http://hdl.handle.net/11427/16003","outbound_label":"Handle","outbound_source":"dc:identifier.uri"},"metadata_groups":[{"id":"people","label":"People","entries":[{"key":"dc:contributor.advisor","label":"Advisor","values":["Elsworth, J F","Jackson, Graham Ellis"]},{"key":"dc:creator","label":"Author","values":["Msimang, Nkosinathi Lorenzo"]}]},{"id":"academic_context","label":"Academic Context","entries":[{"key":"dc:date.accessioned","label":"Dc Date Accessioned","values":["2015-12-28T06:11:05Z"]},{"key":"dc:date.available","label":"Dc Date Available","values":["2015-12-28T06:11:05Z"]},{"key":"dc:date.issued","label":"Date","values":["1990"]},{"key":"dc:publisher.department","label":"Dc Publisher Department","values":["Department of Chemistry"]},{"key":"dc:publisher.institution","label":"Dc Publisher Institution","values":["University of Cape Town"]},{"key":"dc:type","label":"Dc Type","values":["Master Thesis"]},{"key":"dc:type.qualificationlevel","label":"Dc Type Qualificationlevel","values":["Masters"]},{"key":"dc:type.qualificationname","label":"Dc Type Qualificationname","values":["MSc"]}]},{"id":"language_rights","label":"Language and Rights","entries":[{"key":"dc:language.iso","label":"Language (ISO)","values":["eng"]}]},{"id":"identifiers","label":"Identifiers","entries":[{"key":"dc:identifier.uri","label":"Identifier URI","values":["http://hdl.handle.net/11427/16003"]}]},{"id":"additional","label":"Additional Metadata","entries":[{"key":"dc:description","label":"Description","values":["Bibliography: page 154."]},{"key":"dc:description.abstract","label":"Abstract","values":["Towards the labelling of biological macromolecules in contrast media, a synthesis of the novel bifunctional amido-ligands N,N' -bis[2-(N'',N''-dimethylamino)ethyl]-4-aminobenzylmalondiamide (67) and the 3-aminopropyl derivative (66) from appropriately C-functionalized malonates by amidation with N,N-dimethylethylenediamine (62) followed by reduction of the respective nitro (64) and cyano (63) groups is described. The synthesis of N,N'-bis[2-(N'',N''-dimethylamino)ethyl]iminodiacetamide (73) from diethyl N-benzyliminodiacetate (79) by amidation· with (62) followed by debenzylation is described. Herein is also reported the unsuccessful attempts to prepare a functionalized pentaamine ligand similar to (73) via the intermediacy of N,N'-bis[2-(N'',N''-dimethylamino)ethyl]-N'''-(2,2-diethoxyethyl) iminodiacetamide (112) whose preparation is also detailed. Attempts to this end via the Mitsunobu and Steglich coupling of N,N' -bis[2-(N'',N''- dimethylamino)ethyl]-N'''-(2-hydroxyethyl)iminodiacetamide (100) with N-tertbutyloxycarbonylglycine (105) also met with failure .. Further failed attempts to secure suitably functionalized intermediates by N-alkylation of diethyl iininodiacetate (70) with appropriate electrophiles are described. The successful functionalization of the pentaamine series of ligands by N-alkylation of (73) withpnitrobenzoyl chloride (118) to give N,N' -bis[2-(N'',N''- dimethylamino)ethyl] N''' -(4-nitrobenzamido)iminodiacetamide (119) is presented. The preparation of the non-functionalized novel trioxo heptaamine ligand N,N' ,N''-tris[2-(N'',N''-dimethylamino)ethyl]nitrilotriacetamide hydrochloride (86a) is also described. An investigative study towards the assembly of a novel triamine system for encapsulating NMR or isotopic NMR-active metal ions for possible use in diagnostic medicine is reported. The key facet to this end is the reported preparation of N,N' ,N''-tris(2-aminoethyl)propane-1,2,3-tricarboxamide (89) by controlled amidation of trimethyl propane 1,2,3-tricarboxylate (88) with ethylenediamine. The syntheses of functionalized and non-functionalized novel tetraamine dioxo and trioxo ligands from glycine, ethyl N-benzylglycinate (78), L-valine, and L-lysine via classical peptide synthesis methodology (in part) are described."]},{"key":"dc:title","label":"Title","values":["Syntheses of novel acyclic amino-amido ligands"]}]}],"canonical_facts":{"dc:contributor.advisor":["Elsworth, J F","Jackson, Graham Ellis"],"dc:creator":["Msimang, Nkosinathi Lorenzo"],"dc:date.accessioned":["2015-12-28T06:11:05Z"],"dc:date.available":["2015-12-28T06:11:05Z"],"dc:date.issued":["1990"],"dc:description":["Bibliography: page 154."],"dc:description.abstract":["Towards the labelling of biological macromolecules in contrast media, a synthesis of the novel bifunctional amido-ligands N,N' -bis[2-(N'',N''-dimethylamino)ethyl]-4-aminobenzylmalondiamide (67) and the 3-aminopropyl derivative (66) from appropriately C-functionalized malonates by amidation with N,N-dimethylethylenediamine (62) followed by reduction of the respective nitro (64) and cyano (63) groups is described. The synthesis of N,N'-bis[2-(N'',N''-dimethylamino)ethyl]iminodiacetamide (73) from diethyl N-benzyliminodiacetate (79) by amidation· with (62) followed by debenzylation is described. Herein is also reported the unsuccessful attempts to prepare a functionalized pentaamine ligand similar to (73) via the intermediacy of N,N'-bis[2-(N'',N''-dimethylamino)ethyl]-N'''-(2,2-diethoxyethyl) iminodiacetamide (112) whose preparation is also detailed. Attempts to this end via the Mitsunobu and Steglich coupling of N,N' -bis[2-(N'',N''- dimethylamino)ethyl]-N'''-(2-hydroxyethyl)iminodiacetamide (100) with N-tertbutyloxycarbonylglycine (105) also met with failure .. Further failed attempts to secure suitably functionalized intermediates by N-alkylation of diethyl iininodiacetate (70) with appropriate electrophiles are described. The successful functionalization of the pentaamine series of ligands by N-alkylation of (73) withpnitrobenzoyl chloride (118) to give N,N' -bis[2-(N'',N''- dimethylamino)ethyl] N''' -(4-nitrobenzamido)iminodiacetamide (119) is presented. The preparation of the non-functionalized novel trioxo heptaamine ligand N,N' ,N''-tris[2-(N'',N''-dimethylamino)ethyl]nitrilotriacetamide hydrochloride (86a) is also described. An investigative study towards the assembly of a novel triamine system for encapsulating NMR or isotopic NMR-active metal ions for possible use in diagnostic medicine is reported. The key facet to this end is the reported preparation of N,N' ,N''-tris(2-aminoethyl)propane-1,2,3-tricarboxamide (89) by controlled amidation of trimethyl propane 1,2,3-tricarboxylate (88) with ethylenediamine. The syntheses of functionalized and non-functionalized novel tetraamine dioxo and trioxo ligands from glycine, ethyl N-benzylglycinate (78), L-valine, and L-lysine via classical peptide synthesis methodology (in part) are described."],"dc:identifier.uri":["http://hdl.handle.net/11427/16003"],"dc:language.iso":["eng"],"dc:publisher.department":["Department of Chemistry"],"dc:publisher.institution":["University of Cape Town"],"dc:title":["Syntheses of novel acyclic amino-amido ligands"],"dc:type":["Master Thesis"],"dc:type.qualificationlevel":["Masters"],"dc:type.qualificationname":["MSc"]},"updated_at":"2026-07-24T01:33:54Z"}