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Synthesis of Uracil Containing Precursors and Analogues Of Cylindrospermopsin

Fituri, Hisham Saleh (2015) Synthesis of Uracil Containing Precursors and Analogues Of Cylindrospermopsin. PhD thesis, Prifysgol Bangor University.

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Abstract

The thesis covers three topics: i) Synthesis of the uracil D-ring precursor of the cylindrospermopsin alkaloids: this study entailed the preparation of compounds I and II which were shown to be a RHS D-ring precursor in the synthesis of the cylindrospermopsin alkaloids. Compound I was prepared in 3 steps and in 24% overall yield from dibenzylurea whilst II was prepared from either diethyl 1,3-acetonedicarboxylate in 5 steps and 9% overall yield or barbituric acid in 5 steps and 16% overall yield. ii) Preparation of analogues of cylindrospermopsin: the synthesis of the cylindrospermopsin analogue III was achieved in 6 steps and 12% overall yield from the literature compound 2,6-dimethoxypyrimidine-4-carboxaldehyde. iii) Preparation and enzymatic studies on 2.4-dinitrobenzamide pro-drugs: the known pro-drugs IV (X = Cl, Br, I), were prepared and found to be good substrates for the enzyme NfsA NTR. These can thus be considered as alternative pro-drugs to the usually employed CB 1954 in combination with NfsA NTR for human chemotherapy.

Item Type: Thesis (PhD)
Subjects: Degree Thesis
Departments: College of Physical and Applied Sciences > School of Chemistry
Degree Thesis
Date Deposited: 28 Oct 2016 08:38
Last Modified: 28 Oct 2016 08:38
URI: http://e.bangor.ac.uk/id/eprint/8110
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