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Studies toward the total syntheses of heterocyclic analogues of adriamycin

The design and synthesis of two heterocyclic thioanalogues of 7-deoxy daunomycinone, 9-acetyl-6,9,11-trihydroxythioxantho{2,3-g}- and -{3,2-g}tetralin, was accomplished. Various synthetic methodologies to accomplish this were evaluated and two key steps necessary for this synthesis were developed. The first consisted of a novel annulative synthetic sequence utilizing a biacetyl synthon, 3,3-diethoxy-2-butanone cyclohexylimine, and an ortho bis-halomethylarene. The second consisted of the use of o-chlorosulfenylbenzoyl chloride as a thiosalicyclic acid equivalent. Model studies toward the further elaboration of these 7-deoxy aglycones to the active glycosides were also studied. / In addition, 1-{{2-{(2-dydroxyethyl)amino}ethyl}amino}-4-hydroxythioxanthone was prepared and found not to have antitumor properties against P-388 leukemia in vivo.

Identiferoai:union.ndltd.org:LACETR/oai:collectionscanada.gc.ca:QMM.71910
Date January 1983
CreatorsHonek, John Frank.
PublisherMcGill University
Source SetsLibrary and Archives Canada ETDs Repository / Centre d'archives des thèses électroniques de Bibliothèque et Archives Canada
LanguageEnglish
Detected LanguageEnglish
TypeElectronic Thesis or Dissertation
Formatapplication/pdf
CoverageDoctor of Philosophy (Department of Chemistry.)
RightsAll items in eScholarship@McGill are protected by copyright with all rights reserved unless otherwise indicated.
Relationalephsysno: 000194973, proquestno: AAINK66652, Theses scanned by UMI/ProQuest.

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