Syntheses of novel acyclic amino-amido ligands

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dc.contributor.advisorElsworth, J Fen_ZA
dc.contributor.advisorJackson, Graham Ellisen_ZA
dc.contributor.authorMsimang, Nkosinathi Lorenzoen_ZA
dc.date.accessioned2015-12-28T06:11:05Z
dc.date.available2015-12-28T06:11:05Z
dc.date.issued1990en_ZA
dc.descriptionBibliography: page 154.en_ZA
dc.description.abstractTowards 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.en_ZA
dc.identifier.apacitationMsimang, N. L. (1990). <i>Syntheses of novel acyclic amino-amido ligands</i>. (Thesis). University of Cape Town ,Faculty of Science ,Department of Chemistry. Retrieved from http://hdl.handle.net/11427/16003en_ZA
dc.identifier.chicagocitationMsimang, Nkosinathi Lorenzo. <i>"Syntheses of novel acyclic amino-amido ligands."</i> Thesis., University of Cape Town ,Faculty of Science ,Department of Chemistry, 1990. http://hdl.handle.net/11427/16003en_ZA
dc.identifier.citationMsimang, N. 1990. Syntheses of novel acyclic amino-amido ligands. University of Cape Town.en_ZA
dc.identifier.ris TY - Thesis / Dissertation AU - Msimang, Nkosinathi Lorenzo AB - 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. DA - 1990 DB - OpenUCT DP - University of Cape Town LK - https://open.uct.ac.za PB - University of Cape Town PY - 1990 T1 - Syntheses of novel acyclic amino-amido ligands TI - Syntheses of novel acyclic amino-amido ligands UR - http://hdl.handle.net/11427/16003 ER - en_ZA
dc.identifier.urihttp://hdl.handle.net/11427/16003
dc.identifier.vancouvercitationMsimang NL. Syntheses of novel acyclic amino-amido ligands. [Thesis]. University of Cape Town ,Faculty of Science ,Department of Chemistry, 1990 [cited yyyy month dd]. Available from: http://hdl.handle.net/11427/16003en_ZA
dc.language.isoengen_ZA
dc.publisher.departmentDepartment of Chemistryen_ZA
dc.publisher.facultyFaculty of Scienceen_ZA
dc.publisher.institutionUniversity of Cape Town
dc.subject.otherChemistryen_ZA
dc.titleSyntheses of novel acyclic amino-amido ligandsen_ZA
dc.typeMaster Thesis
dc.type.qualificationlevelMasters
dc.type.qualificationnameMScen_ZA
uct.type.filetypeText
uct.type.filetypeImage
uct.type.publicationResearchen_ZA
uct.type.resourceThesisen_ZA
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