Dacarbazine and its structural analogues : systematic computational studies of the configurations, tautomers, tautomerization pathways and bimolecular nucleophilic substitution reaction mechanisms of dacarbazine : a triazene containing anti-neoplastic agent, and its structural analogues

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dc.contributor.advisor Pye, Cory C.
dc.creator Doucet, Katherine Grace
dc.date.accessioned 2011-05-09T12:31:40Z
dc.date.available 2011-05-09T12:31:40Z
dc.date.issued 2007
dc.identifier.other RS431 A64 D68 2007
dc.identifier.uri http://library2.smu.ca/xmlui/handle/01/22212
dc.description xvii, 181, [192] leaves : ill. (some col.) ; 29 cm.
dc.description Includes abstract and appendix.
dc.description Includes bibliographical references (leaves 172-181).
dc.description.abstract A monomethyltriazene is believed to be the active metabolite of triazene containing anti-neoplastic agents and is thought to methylate the O6-oxygen of guanine to form methylguanine. Methylguanine is believed to be responsible for the observed cytotoxic properties of triazene containing anti-neoplastic agents. Dacarbazine, a triazene containing anti-neoplastic agent, has been shown to be the single most active agent for the treatment of malignant melanoma. Computational studies, including conformational and tautomer analysis, tautomerization pathways and a model mechanism of action, were conducted in the hopes that a better understanding of the chemical and physical properties of triazene containing anti-neoplastic compounds could be provided. This study found that the tautomerization of a monomethyltriazene is a relatively low energy process and the tautomer form will preferentially undergo an S N 2 type reaction. It is proposed that following demethylation DTIC would preferentially undergo tautomerization followed by an S N 2 type reaction to form methylguanine.
dc.description.provenance Made available in DSpace on 2011-05-09T12:31:40Z (GMT). No. of bitstreams: 0 en
dc.language.iso en
dc.publisher Halifax, N.S. : Saint Mary's University
dc.subject.lcc RS431.A64
dc.subject.lcsh Antineoplastic agents -- Structure
dc.subject.lcsh Chemistry -- Computer simulation
dc.subject.lcsh Tautomerism
dc.subject.lcsh Substitution reactions
dc.subject.lcsh Nucleophilic reactions
dc.title Dacarbazine and its structural analogues : systematic computational studies of the configurations, tautomers, tautomerization pathways and bimolecular nucleophilic substitution reaction mechanisms of dacarbazine : a triazene containing anti-neoplastic agent, and its structural analogues
dc.type Text
thesis.degree.name Master of Science in Applied Science
thesis.degree.level Masters
thesis.degree.discipline Chemistry
thesis.degree.grantor Saint Mary's University (Halifax, N.S.)
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