Please use this identifier to cite or link to this item: https://hdl.handle.net/1959.11/5016
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dc.contributor.authorWang, Yue-Tingen
dc.contributor.authorJin, Kyoung Jooen
dc.contributor.authorMyers, Lauren Ren
dc.contributor.authorGlover, Stephenen
dc.contributor.authorNovak, Michaelen
dc.date.accessioned2010-03-11T14:42:00Z
dc.date.issued2009en
dc.identifier.citationJournal of Organic Chemistry, 74(12), p. 4463-4471en
dc.identifier.issn1520-6904en
dc.identifier.issn0022-3263en
dc.identifier.urihttps://hdl.handle.net/1959.11/5016en
dc.description.abstract4-Acetoxy-4-(benzothiazol-2-yl)-2,5-cyclohexadien-1-one, 1, a quinol derivative that exhibits significant anti-tumor activity against human breast, colon, and renal cancer cell lines, undergoes hydrolysis in aqueous solution to generate an oxenium ion intermediate, 3, that is selectively trapped by N3 - in an aqueous environment. The 4-(benzothiazol-2-yl) substituent slows the rate of ionization of 1 compared to analogues with 4-phenyl or 4-(p-tolyl) substituents, 4a or 4b. However, once generated, 3 is somewhat more selective than the 4-phenyl-substituted cation 5a. Calculations performed at the B3LYP/6-31G(d) level agree that the 4-(benzothiazol-2-yl) substituent does significantly stabilize 3. The structure of the major isolated azide adduct, 4-(6-azidobenzothiazol-2-yl)phenol, 9, confirms that the positive charge is highly delocalized in 3. The results of hydrolysis of 1 show that the 4-(benzothiazol-2-yl) substituent has a significant inductive electron-withdrawing effect as well as a significant resonance effect that is electron-donating. Photolysis of 1 in aqueous solution generates the quinol 2 as one of several photolysis products. The presence of the quinol suggests that photolysis also leads, in part, to generation of 3, but photoionization of 1 is significantly less efficient than is the case for the esters 4a and 4b. This study proves that 3 is generated by ionization of 1 in an aqueous environment. A significant number of other 2-benzothiazole derivatives that are not quinols, including ring-substituted derivatives of 2-(4-aminophenyl)benzothiazole 15, are under development as anti-tumor agents as well. The possible generation of the reactive intermediate 17 by hydrolysis of the putative metabolite 16 is under investigation.en
dc.languageenen
dc.publisherAmerican Chemical Societyen
dc.relation.ispartofJournal of Organic Chemistryen
dc.titleHydrolysis and Photolysis of 4-Acetoxy-4-(benzothiazol-2-yl)-2,5-cyclohexadien-1-one, a Model Anti-Tumor Quinol Esteren
dc.typeJournal Articleen
dc.subject.keywordsTheoretical and Computational Chemistryen
dc.subject.keywordsBiologically Active Moleculesen
dc.subject.keywordsPhysical Organic Chemistryen
local.contributor.firstnameYue-Tingen
local.contributor.firstnameKyoung Jooen
local.contributor.firstnameLauren Ren
local.contributor.firstnameStephenen
local.contributor.firstnameMichaelen
local.subject.for2008030799 Theoretical and Computational Chemistry not elsewhere classifieden
local.subject.for2008030505 Physical Organic Chemistryen
local.subject.for2008030401 Biologically Active Moleculesen
local.subject.seo2008970111 Expanding Knowledge in the Medical and Health Sciencesen
local.subject.seo2008970103 Expanding Knowledge in the Chemical Sciencesen
local.profile.schoolSchool of Science and Technologyen
local.profile.emailsglover@une.edu.auen
local.output.categoryC1en
local.record.placeauen
local.record.institutionUniversity of New Englanden
local.identifier.epublicationsrecordune-20090813-133642en
local.publisher.placeUnited States of Americaen
local.format.startpage4463en
local.format.endpage4471en
local.peerreviewedYesen
local.identifier.volume74en
local.identifier.issue12en
local.contributor.lastnameWangen
local.contributor.lastnameJinen
local.contributor.lastnameMyersen
local.contributor.lastnameGloveren
local.contributor.lastnameNovaken
dc.identifier.staffune-id:sgloveren
local.profile.roleauthoren
local.profile.roleauthoren
local.profile.roleauthoren
local.profile.roleauthoren
local.profile.roleauthoren
local.identifier.unepublicationidune:5133en
dc.identifier.academiclevelAcademicen
local.title.maintitleHydrolysis and Photolysis of 4-Acetoxy-4-(benzothiazol-2-yl)-2,5-cyclohexadien-1-one, a Model Anti-Tumor Quinol Esteren
local.output.categorydescriptionC1 Refereed Article in a Scholarly Journalen
local.description.statisticsepubsVisitors: 297<br />Views: 321<br />Downloads: 0en
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