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dc.contributor.advisorDavis, Franklin A.
dc.contributor.advisorAndrade, Rodrigo B.
dc.creatorGardner, Alexander Charles
dc.date.accessioned2022-05-26T18:18:43Z
dc.date.available2022-05-26T18:18:43Z
dc.date.issued2022
dc.identifier.urihttp://hdl.handle.net/20.500.12613/7731
dc.description.abstractThe first semi-synthesis of (-)-melodinine K was completed from the monoterpene indole alkaloid (-)-tabersonine through regioselective enzymatic hydroxylation and Polonovski-Potier coupling. Regioselective borylation strategies were used to achieve meta-oxygenated derivatives of (-)-tabersonine for analysis in a Drosophila fruit fly Alzheimer’s phenotype model. A library of oxygenated and epoxidized bis-indole alkaloid analogs in the taberyunine class were prepared to conduct a structure activity relationship (SAR) study of the bis-indole framework against colon cancer and melanoma cell lines. Alkaloid aryl trifluoroborates were synthesized to increase nucleophilicity of arenes for unfavored alpha-arylations of tertiary amines on route to melosuavine bis-indole alkaloids. Overall, nine new bis-indole alkaloids were synthesized in the melodinine, taberyunine, and melosuavine class that showed strong cytotoxicity against a variety of melanoma, colon cancer, and renal cancer cell lines.
dc.format.extent281 pages
dc.language.isoeng
dc.publisherTemple University. Libraries
dc.relation.ispartofTheses and Dissertations
dc.rightsIN COPYRIGHT- This Rights Statement can be used for an Item that is in copyright. Using this statement implies that the organization making this Item available has determined that the Item is in copyright and either is the rights-holder, has obtained permission from the rights-holder(s) to make their Work(s) available, or makes the Item available under an exception or limitation to copyright (including Fair Use) that entitles it to make the Item available.
dc.rights.urihttp://rightsstatements.org/vocab/InC/1.0/
dc.subjectOrganic chemistry
dc.subjectAlkaloids
dc.subjectBiotransformation
dc.subjectBis-indole
dc.subjectMelodinine K
dc.subjectNatural products
dc.subjectTabersonine
dc.titleSemi-Synthesis of Melodinine, Taberyunine, and Melosuavine Bis-Indole Alkaloids Through Chemical and Biological Methods
dc.typeText
dc.type.genreThesis/Dissertation
dc.contributor.committeememberWengryniuk, Sarah E.
dc.contributor.committeememberSieburth, Scott McNeill
dc.contributor.committeememberCannon, Kevin C.
dc.description.departmentChemistry
dc.relation.doihttp://dx.doi.org/10.34944/dspace/7703
dc.ada.noteFor Americans with Disabilities Act (ADA) accommodation, including help with reading this content, please contact scholarshare@temple.edu
dc.description.degreePh.D.
dc.identifier.proqst14852
dc.date.updated2022-05-11T16:10:47Z
refterms.dateFOA2022-05-26T18:18:43Z
dc.identifier.filenameGardner_temple_0225E_14852.pdf


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