Diels-Alder approaches to anti-cancer prodrugs
| dc.contributor.author | Dyer, Jolon Matthew | en |
| dc.date.accessioned | 2012-08-03T00:29:27Z | |
| dc.date.available | 2012-08-03T00:29:27Z | |
| dc.date.issued | 1998 | en |
| dc.description.abstract | This thesis concerns the design and synthesis of compounds relevant to a new strategy for the synthesis of anti-cancer prodrugs. The focus of this strategy is Diels-Alder chemistry leading to oxygen or sulfur-bridged polycyclic adducts. Bridge cleavage of such adducts can result in the formation of polycyclic, aromatic compounds, a structure characteristic of anti-cancer drugs which act via intercalation. Part A describes the design of a model system for the synthesis of Diels-Alder adducts as prodrugs. A range of isobenzofurans, along with a range of fumaramide and N-aryl maleimide derivatives, were synthesised, and these were reacted together in Diels-Alder fashion. The resulting adducts were bridge cleaved. Part B describes the introduction of functional groups into Diels-Alder adducts. The functional groups investigated included alkylating and hydrogen-bonding substituents, introduced via N-aryl maleimide based dienophiles. A range of isobenzothiophenes was also synthesised, and these were used to generate sulphur-bridged Diels-Alder adducts, with the resulting increase in stability proving advantageous in some instances. A variety of functionalised adducts and their bridge cleaved derivatives were prepared. The biological properties of some showed promise as leads for the development of anti-cancer compounds. | en |
| dc.identifier.uri | http://hdl.handle.net/10092/6781 | |
| dc.identifier.uri | http://dx.doi.org/10.26021/5889 | |
| dc.language.iso | en | |
| dc.publisher | University of Canterbury. Chemistry | en |
| dc.relation.isreferencedby | NZCU | en |
| dc.rights | Copyright Jolon Matthew Dyer | en |
| dc.rights.uri | https://canterbury.libguides.com/rights/theses | en |
| dc.title | Diels-Alder approaches to anti-cancer prodrugs | en |
| dc.type | Theses / Dissertations | |
| thesis.degree.grantor | University of Canterbury | en |
| thesis.degree.level | Doctoral | en |
| thesis.degree.name | Doctor of Philosophy | en |
| uc.bibnumber | 669150 | |
| uc.college | Faculty of Science | en |
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