Design and synthesis of novel sulfur-containing antiviral analogues

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dc.contributor.advisor O'Sullivan, Tim en Jones, David J. 2019-03-08T12:19:34Z 2018 2018
dc.identifier.citation Jones, D. J. 2018. Design and synthesis of novel sulfur-containing antiviral analogues. PhD Thesis, University College Cork. en
dc.identifier.endpage 287 en
dc.description.abstract Chapter One of this thesis presents a consolidated review of methods for the formation of phosphorus-sulfur bonds. This review focuses on the synthesis of phosphorothioates, phosphonothioates, phosphinothioates and phosphonodithioates which are among the most important sulfur-containing organophosphorus compounds and are central to the work described later in the thesis. The medicinal chemistry of the nucleoside reverse transcriptase inhibitor (NRTI) class of anti-HIV compounds is described in Chapter Two. Our proposed synthetic target, an analogue of Adefovir Dipivoxil, is described alongside our rationale for studying this compound. Chapter Three details the model study which we conducted in order to assess possible synthetic routes to our target molecule. The highlight of this work was the development of a general method for the synthesis of various classes of sulfur-containing organophosphorus compounds exploiting the base labile 2-cyanoethyl group as a synthon. Chapters Four and Five describe our various, ultimately unsuccessful attempts at preparing our target molecule and similar compounds employing the chemistry which we developed in the course of our model study. A series of complementary strategies for the construction of key C-C, C-N and P-S bonds in the final compounds are investigated. Avenues for further study on this project are presented within Chapter Six, concluding the work conducted within this thesis. Full experimental procedures, including spectroscopic and analytical data, are given for all previously known and novel compounds prepared during this research in Chapter Seven. en
dc.format.mimetype application/pdf en
dc.language.iso en en
dc.publisher University College Cork en
dc.rights © 2018, David J. Jones. en
dc.rights.uri en
dc.subject Organic chemistry en
dc.subject Organosulfur chemistry en
dc.subject Organophosphorus chemistry en
dc.subject Acyclic nucleoside phosphonate en
dc.title Design and synthesis of novel sulfur-containing antiviral analogues en
dc.type Doctoral thesis en
dc.type.qualificationlevel Doctoral en
dc.type.qualificationname PhD en
dc.internal.availability Full text not available en Indefinite en 10000-01-01
dc.description.version Accepted Version
dc.contributor.funder University College Cork en
dc.description.status Not peer reviewed en Chemistry en
dc.check.reason This thesis contains data which has not yet been published en
dc.check.opt-out Not applicable en
dc.thesis.opt-out false
dc.check.entireThesis Entire Thesis Restricted
dc.check.embargoformat Apply the embargo to both hard bound copy and e-thesis (If you have submitted an e-thesis and a hard bound thesis and want to embargo both) en
dc.internal.conferring Spring 2019 en
dc.internal.ricu Analytical and Biological Chemistry Research Facility en
dc.relation.project University College Cork (Strategic Research Fund) en

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© 2018, David J. Jones. Except where otherwise noted, this item's license is described as © 2018, David J. Jones.
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