Quantitative structure activity relationships of monamine oxidase catalyzed oxidation of 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine analogs

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dc.contributor.authorHarris, Dana N.en
dc.contributor.committeechairCastagnoli, Neal Jr.en
dc.contributor.committeememberTanko, James M.en
dc.contributor.committeememberBevan, David R.en
dc.contributor.committeememberBell, Harold M.en
dc.contributor.departmentChemistryen
dc.date.accessioned2014-03-14T21:43:53Zen
dc.date.adate2008-08-25en
dc.date.available2014-03-14T21:43:53Zen
dc.date.issued1996-05-15en
dc.date.rdate2008-08-25en
dc.date.sdate2008-08-25en
dc.description.abstractStudies into the quantitative structure act! Vlty relationships of rate s of I-methyl-4-phenyl-l,2,3,6-tetrahydropyridine oxidation catalyzed by monoamine oxidases A and B were performed to elucidate active site substrate conformation and oxidation mechanisms. Plotting experimental kinetic activity against molecular properties obtained by experiment and by computational chemistry methods demonstrated correlations with lipophilic, steric, and electronic factors. Compounds studied were 4-aryloxy analogs, 4- aromatic heterocycle analogs, and 4-phenyl analogs. The conformer with phenyl ring to tetrahydropyridine dihedral angles similar to a low energy conformer of I-methyl-4-(2'-methyl-phenyl)-1,2,3,6- tetrahydropyridine is the most active conformer. Results indicate that rate limiting single electron transfer mechanisms are more viable than hydrogen atom abstraction mechanisms. Results indicate that binding or dissociation is the rate limiting step for aryloxy-analog oxidation catalyzed by monoamine oxidase B whereas the catalytic event itself is the rate limiting step for the other analogs. Several equations were developed to describe quantitative structure activity relationships of oxidation rates.en
dc.description.degreeMaster of Scienceen
dc.format.extentviii, 266 leavesen
dc.format.mediumBTDen
dc.format.mimetypeapplication/pdfen
dc.identifier.otheretd-08252008-162914en
dc.identifier.sourceurlhttp://scholar.lib.vt.edu/theses/available/etd-08252008-162914/en
dc.identifier.urihttp://hdl.handle.net/10919/44451en
dc.language.isoenen
dc.publisherVirginia Techen
dc.relation.haspartLD5655.V855_1996.H377.pdfen
dc.relation.isformatofOCLC# 35332688en
dc.rightsIn Copyrighten
dc.rights.urihttp://rightsstatements.org/vocab/InC/1.0/en
dc.subjectParkinson's diseaseen
dc.subjectQSARen
dc.subjectMAOen
dc.subjectMPTPen
dc.subject.lccLD5655.V855 1996.H377en
dc.titleQuantitative structure activity relationships of monamine oxidase catalyzed oxidation of 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine analogsen
dc.typeThesisen
dc.type.dcmitypeTexten
thesis.degree.disciplineChemistryen
thesis.degree.grantorVirginia Polytechnic Institute and State Universityen
thesis.degree.levelmastersen
thesis.degree.nameMaster of Scienceen

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