Design and synthesis of novel sulfur-containing antiviral analogues

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Jones, David J.
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University College Cork
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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.
Organic chemistry , Organosulfur chemistry , Organophosphorus chemistry , Acyclic nucleoside phosphonate
Jones, D. J. 2018. Design and synthesis of novel sulfur-containing antiviral analogues. PhD Thesis, University College Cork.