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Title: Design and synthesis of novel sulphur containing biocides
Author: Matthews, T. P.
Awarding Body: University of Wales Swansea
Current Institution: Swansea University
Date of Award: 2000
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A literature search suggested that small, easily absorbable sulphur containing compounds, may react with intercellular thiols in a similar manner to well established biocides such as the 3-isothiazolones. As this reaction is linked with the biocide’s mode of action, the biological efficacy of these types of molecules, more specifically the nitrothiophenes, were studied using QSAR techniques to rationalize their activity. A series of seventeen structurally diverse nitrothiophene derivatives were synthesized by a variety of, in many cases, previously undocumented synthetic routes. These compounds, four of which were novel, were characterised by 1H, 13C NMR, IR , and accurate mass spectroscopy. A total of twenty nitrothiophene derivatives were evaluated for their potential biological activity, by identifying the minimum inhibitory concentrations required to inhibit actively growing E. coli, M. luteus, and A. niger cultures via agar diffusion techniques. Semi-empirical molecular orbital methods were employed to model the nitrothiophene derivatives and establish a set of calculated physiochemical properties of each of them. The solvent dielectric continuum model (COSMO) was also used to predict the structures and properties whilst in the aqueous environment of the cell. Several multilinear regression techniques were used to produce four QSAR models using the previously calculated properties, to explain the varying degrees of biological activity of the nitrothiophene derivatives against both the E. coli and M. luteus bacteria in both a membrane and aqueous environment., Each model was statistically significant to the 5% level and showed a good correlation to the data it described. The model’s predictive statistics showed that they are sufficiently robust to be utilised to predict the activity of other nitrothiophene derivatives.
Supervisor: Not available Sponsor: Not available
Qualification Name: Thesis (Ph.D.) Qualification Level: Doctoral
EThOS ID:  DOI: Not available