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Title: The synthesis of nucleoside analogues from nitroimidazole precursors.
Author: Clayton, Russell.
Awarding Body: University of Keele
Current Institution: Keele University
Date of Award: 2001
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An introduction to nucleoside analogues containing heterocyclic sugar mimics and their synthesis is presented. This includes various ring sizes and different heteroatom combinations. concentrated on work between 1995-2000. The synthesis of novel nucleoside analogues from nitroimidazole precursors has been investigated. The regioisorners I-vinyl-4-nitroimidazole and I-vinyl-S-nitroimidazole have been synthesised from the readily available 4/S-nitroimidazole. Also synthesised from 4/S-nitroimidazoIe IS 3-vinyl-imidazo[ 4' ,S' :S,6]pyrido[2,3- d]pyrimidin-8-one, the pyridine stretched analogue of 3-vinylinosine. 1,3-Dipolar cycloaddition reactions of these three molecules are studied, with stabilised and unstabilised 1,3-dipolar compounds. to produce heterocyclic nucleoside analogues. Structures of these cycloadducts are investigated using nrnr studies to determine the regiochemistry of the reactions. This nrnr evidence is supported my MO calculations. Further studies have established synthetic routes to the pyridine stretched analogues of 2'-deoxyadenosine and 2'-deoxyinosine from deoxyribose and 4/5- nitroimidazole, involving directing the coupling of a chlorosugar to the sodium salt of 4-nitroimidazoIe to yield a maximum of the S-nitroimidazole isomer product
Supervisor: Not available Sponsor: Not available
Qualification Name: Thesis (Ph.D.) Qualification Level: Doctoral
EThOS ID:  DOI: Not available
Keywords: 1,3-dipolar; 2'-deoxyadenosine; 2'-deoxyinosine Chemistry, Organic