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Cross-coupling reactions: synthesis and photoactivity of enediynes

dc.contributor.advisorGottardo, Christine
dc.contributor.authorQuance, Melissa
dc.date.accessioned2015-02-02T15:41:35Z
dc.date.available2015-02-02T15:41:35Z
dc.date.created2015
dc.date.issued2015-02-02
dc.identifier.urihttp://knowledgecommons.lakeheadu.ca/handle/2453/614
dc.description.abstractThe syntheses of a number of photoactive enediynes using the Sonogashira Coupling reaction are described. Alkynes with different characteristics were coupled to 2-bromoiodobenzene to yield the desired drugs. The enediyne’s functionality and their ability to undergo the Bergman Cyclization reaction is of interest given that a variety of naturally occurring and few synthetically produced compounds containing this unit demonstrate the ability to cleave DNA. The compounds were tested against human alveolar type 11-epithelial A549 cancer cells and the non-cancer cell line H9c2 and it was found that in the presence of light, they showed an enhanced ability to increase cell death. The enediyne with electron withdrawing functionality resulted in the greatest increase in cell death. In addition, an independent study on the direct arylation of heteroaromatic arenes with benzene was undertaken. In this study, substituted furans were treated under palladium-catalyzed conditions in the presence of benzene to synthesize biaryl compounds from unactivated starting materials. The presence of the electron with drawing aldehyde resulted in best yield of cross-coupling product.en_US
dc.language.isoen_USen_US
dc.subjectEnediyne chemistryen_US
dc.subjectEnediyne anticancer agentsen_US
dc.subjectCycloaromatizationen_US
dc.subjectEnzymatic triggeringen_US
dc.subjectPhotochemical triggeringen_US
dc.subjectCross-couplingen_US
dc.titleCross-coupling reactions: synthesis and photoactivity of enediynesen_US
dc.typeThesisen_US
etd.degree.nameM.Sc.en_US
etd.degree.levelMasteren_US
etd.degree.disciplineChemistryen_US
etd.degree.grantorLakehead Universityen_US
dc.contributor.committeememberJiang, Zi-Hua (Justin)
dc.contributor.committeememberSuntres, Zach


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