Novel acyclic nucleotide phosphonates against RNA viruses

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dc.contributor.advisorHunter, Rogeren_ZA
dc.contributor.authorBowden, Gregory Daviden_ZA
dc.date.accessioned2014-12-27T14:16:33Z
dc.date.available2014-12-27T14:16:33Z
dc.date.issued2012en_ZA
dc.descriptionIncludes bibliographical references.en_ZA
dc.description.abstractAcyclic nucleotide phosphonates (ANPs) have been used for years as successful anti-viral agents against diseases such as HIV/AIDS and hepatitis while the drug ribavirin is one of the only drugs available for the treatment of RNA-viral infections which mainly affect the developing world. The large and unmet need for anti-RNA viral treatments has prompted this study into the design and synthesis of a range of ANPs, which includes a series of ribavirin-based ANP derivatives. The series of compounds was synthesised from a diisopropyl protected phosphonomethoxyethyl (PME) synthon and included an arylethynyltriazole derivative which was produced via a Sonogashira palladium catalysed cross-coupling reaction. A selection of these compounds was then deprotected to their corresponding phosphonic acids via a bromotrimethylsilane mediated phosphonate ester hydrolysis. In one example, a bis(pivaloyloxymethyl) prodrug variant was produced in order to probe a general synthesis for prodrug protected ANP derivatives. All new compounds were characterised by NMR, IR, and Mass spectroscopic techniques.en_ZA
dc.identifier.apacitationBowden, G. D. (2012). <i>Novel acyclic nucleotide phosphonates against RNA viruses</i>. (Thesis). University of Cape Town ,Faculty of Science ,Department of Chemistry. Retrieved from http://hdl.handle.net/11427/10258en_ZA
dc.identifier.chicagocitationBowden, Gregory David. <i>"Novel acyclic nucleotide phosphonates against RNA viruses."</i> Thesis., University of Cape Town ,Faculty of Science ,Department of Chemistry, 2012. http://hdl.handle.net/11427/10258en_ZA
dc.identifier.citationBowden, G. 2012. Novel acyclic nucleotide phosphonates against RNA viruses. University of Cape Town.en_ZA
dc.identifier.ris TY - Thesis / Dissertation AU - Bowden, Gregory David AB - Acyclic nucleotide phosphonates (ANPs) have been used for years as successful anti-viral agents against diseases such as HIV/AIDS and hepatitis while the drug ribavirin is one of the only drugs available for the treatment of RNA-viral infections which mainly affect the developing world. The large and unmet need for anti-RNA viral treatments has prompted this study into the design and synthesis of a range of ANPs, which includes a series of ribavirin-based ANP derivatives. The series of compounds was synthesised from a diisopropyl protected phosphonomethoxyethyl (PME) synthon and included an arylethynyltriazole derivative which was produced via a Sonogashira palladium catalysed cross-coupling reaction. A selection of these compounds was then deprotected to their corresponding phosphonic acids via a bromotrimethylsilane mediated phosphonate ester hydrolysis. In one example, a bis(pivaloyloxymethyl) prodrug variant was produced in order to probe a general synthesis for prodrug protected ANP derivatives. All new compounds were characterised by NMR, IR, and Mass spectroscopic techniques. DA - 2012 DB - OpenUCT DP - University of Cape Town LK - https://open.uct.ac.za PB - University of Cape Town PY - 2012 T1 - Novel acyclic nucleotide phosphonates against RNA viruses TI - Novel acyclic nucleotide phosphonates against RNA viruses UR - http://hdl.handle.net/11427/10258 ER - en_ZA
dc.identifier.urihttp://hdl.handle.net/11427/10258
dc.identifier.vancouvercitationBowden GD. Novel acyclic nucleotide phosphonates against RNA viruses. [Thesis]. University of Cape Town ,Faculty of Science ,Department of Chemistry, 2012 [cited yyyy month dd]. Available from: http://hdl.handle.net/11427/10258en_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.titleNovel acyclic nucleotide phosphonates against RNA virusesen_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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