Synthesis and Chemistry of Novel Aryl Sulfonamides and Initial Studies of Their Biological Activity
Soumehsaraei, Shohreh J.
Soumehsaraei, Shohreh J.
Publication Date
End of Embargo
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The University of Bradford theses are licenced under a Creative Commons Licence.
Peer-Reviewed
Open Access status
Accepted for publication
Institution
University of Bradford
Department
School of Chemistry and Biosciences. Faculty of Life Sciences
Awarded
2023
Embargo end date
2027-01-21
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Abstract
This thesis describes novel rearrangement chemistry of aryl and heteroaryl sulphonamides, and anti-cancer testing of a subset of the compounds made.
Additionally, biological testing was conducted on a small library of structural analogues of Gallic acid.
Studies were conducted to expand the scope of a previously reported nitrogen to carbon rearrangement reaction that had been shown to deliver quaternary unnatural amino acids. It was found that the rearrangement of the pyrimidine moiety was possible, and the resultant amino acid was formed with good yield. Attempts to expand the reaction to other amino acid / heterocycles proved challenging.
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The amino acid derived from the experiment underwent assessment for its anticancer
potential. Both the CCK-8 assay, and comet assay were employed to verify its anticancer properties.
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The scope of the rearrangement was further explored to give aryl products with increased substitution, and to give access to rearranged products where the termination of rearrangement was a tolyl group. The steric and electronic control factors for the aryl verses tolyl rearrangement were explored.
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Finally, a set of gallic acid analogues were synthesised, where the introduction of a primary sulphonamide in the place of carboxylic group(-COOH), and methylation of the hydroxyl groups was explored. The genotoxic effects of the compounds this made were examined by using a comet assay.
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Type
Thesis
Qualification name
PhD
Notes
The full text will be available at the end of the embargo: 21st Jan 2027