Synthesis of novel lavendamycin analogues and related heterocyclic containing quinolone-5,8-diones

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dc.contributor.advisor Sammelson, Robert E.
dc.contributor.author Ravanfar, Raheleh
dc.date.accessioned 2016-07-27T17:39:56Z
dc.date.available 2016-07-27T17:39:56Z
dc.date.issued 2016-07-23
dc.identifier.uri http://cardinalscholar.bsu.edu/handle/123456789/200336
dc.description.abstract Lavendamycin is a quinoline-5,8-dione antibiotic and antitumor agent with a pentacyclic structure including the 7-aminoquinoline-5,8-dione and the indolopyridine (β-carboline) moieties. Despite the interest in lavendamycin as an antitumor agent, this agent was precluded from preclinical development due to its poor aqueous solubility and its toxicity toward normal human cells. Lavendamycin has been the focus of several synthetic studies to elucidate the structural features that are required for its cytotoxic activity and to develop improved analogues with potent antitumor properties and lower animal toxicity. The purpose of the present study is to synthesize new lavendamycin analogues by changing the functionality, at the C2 position of the quinoline-5,8-dione, and investigate the new analogues’ reactivity with the NQO1 enzyme. Therefore, 7-N-acylamidoquinoline-5,8-dione-2- carboxaldehyde oximes were synthesized in 7 steps from commercially available 8-hydroxy-2- methyl quinoline. 7-N-(acetamido, propionamido, butyramido and isobutyramido)-5,8-dione VII aldehyde, and finally oxime formation. Several 3-(7-N-acylamido-5,8-quinolinedion-2-yl)-5-tbutylisoxazoline and 3-(7-N-acylamido-5,8-quinolinedion-2-yl)-5-methoxymethylisoxazole derivatives were synthesized in good to excellent yields. The new analogues were characterized by 1H-NMR, 13C-NMR and IR spectroscopy.
dc.description.sponsorship Department of Chemistry
dc.description.tableofcontents An introduction to lavendamycin antitumor agents -- Synthesis of novel lavendamycin analogues and related heterocyclic containing quinoline-5, 8-diones.
dc.subject.lcsh Antineoplastic agents -- Synthesis.
dc.subject.lcsh Quinoline -- Derivatives.
dc.title Synthesis of novel lavendamycin analogues and related heterocyclic containing quinolone-5,8-diones en_US
dc.description.degree Thesis (M.S.) en_US
dc.identifier.cardcat-url http://liblink.bsu.edu/catkey/1828200


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  • Master's Theses [5293]
    Master's theses submitted to the Graduate School by Ball State University master's degree candidates in partial fulfillment of degree requirements.

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