Goodworth, Kerry Joanne; (2003) Synthesis of phenylcalixarenes and analogues for use as tuberculosis therapies. Doctoral thesis (Ph.D), UCL (University College London).

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Abstract

Initially the literature in the area is reviewed. The first chapter details current TB therapies and trends in TB, whilst the second chapter reviews the synthesis of macrocyclic TB therapies, and the synthesis and reactions of calixarenes.In Chapter 3 the synthesis of phenylcalixarenes is discussed, and a templating effect upon product distribution established. Synthesis of the tert-butyl octamer and hexamer, and the nude calix[8]arene and calix[6]arene is also discussed. Sulfonation and acylation of the upper rim of the nude calixarenes is also discussed.In Chapter 4 the synthesis of PEG-chains via protection and activation strategies is discussed. In Chapter 5 PEGylation of phenylcalix[8]arene and phenylcalix[7]arene is described, and a difference in reactivity of the octamer and heptamer towards PEG- chains is discussed. Derivatisation of the octamer and heptamer with alkyl nitrile chains is also described, as is derivatisation of the octamer with active electrophiles.In Chapter 6 the synthesis of a series of small PEGylated analogues, and fluorescently labelled compounds is discussed. In Chapter 7 the results of biological testing of compounds synthesised are presented, and Chapter 8 concludes the thesis and presents ideas for future work. The final chapter describes the experimental methods employed.

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