Design, Synthesis and Evaluation of Heterocyclic Compounds for Antibacterial Applications

Phillips, Matthew James Anthony

Design, Synthesis and Evaluation of Heterocyclic Compounds for Antibacterial Applications

Phillips, Matthew James Anthony

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Publication Type:: Thesis
Issue Date:: 2024

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Field	Value	Language
dc.contributor.author	Phillips, Matthew James Anthony
dc.date.accessioned	2024-10-01T06:37:28Z
dc.date.available	2024-10-01T06:37:28Z
dc.date.issued	2024
dc.identifier.uri	http://hdl.handle.net/10453/181127
dc.description	University of Technology Sydney. Faculty of Science.	en_US.UTF-8
dc.description.abstract	With the rise of antibacterial resistance in numerous pathogens, novel chemical scaffolds are required to treat bacterial infections. In this context, 4-chloroisocoumarin and isoquinoline compounds have previously been shown to have a range of pharmacological activities. In this thesis, 3-alkoxy-4-chloroisocoumarin compounds were investigated for their anti-chlamydial properties, targeting the conserved serine protease High-temperature requirement A in Chlamydia trachomatis. The synthesis of a new series of isocoumarin-based compounds was developed, and their anti-chlamydial activity was investigated. The structure of the alkoxy substituent influenced the potency of the compounds against High-temperature requirement A, and modifications to the C-7 position of the 3-alkoxy-4-chloroisocoumarin structure affected anti-chlamydial properties. The compounds were found to be inactive against Chlamydia pecorum. Separately, a new series of compounds based on a tricyclic isoquinoline scaffold was investigated, with activity identified against gram-positive pathogens. However, cytotoxic properties were also identified against mammalian cell lines, which may limit their potential as antibacterial agents.	en_US.UTF-8
dc.format	Thesis (PhD)
dc.language.iso	en_US	en_US.UTF-8
dc.relation	https://opus.lib.uts.edu.au/bitstream/10453/181127/1/thesis.pdf
dc.rights	info:eu-repo/semantics/openAccess
dc.rights	The author owns the copyright in this thesis including all reproduction and reuse rights for the work. The work may not be altered without the permission of the copyright owner. Attribution is essential when quoting or paraphrasing from this thesis.
dc.rights	© 2024 Matthew James Anthony Phillips
dc.rights	au.edu.uts.lib/cph
dc.title	Design, Synthesis and Evaluation of Heterocyclic Compounds for Antibacterial Applications	en_US.UTF-8
dc.type	Thesis
utslib.copyright.status	open_access	*

Abstract:

With the rise of antibacterial resistance in numerous pathogens, novel chemical scaffolds are required to treat bacterial infections. In this context, 4-chloroisocoumarin and isoquinoline compounds have previously been shown to have a range of pharmacological activities. In this thesis, 3-alkoxy-4-chloroisocoumarin compounds were investigated for their anti-chlamydial properties, targeting the conserved serine protease High-temperature requirement A in Chlamydia trachomatis. The synthesis of a new series of isocoumarin-based compounds was developed, and their anti-chlamydial activity was investigated. The structure of the alkoxy substituent influenced the potency of the compounds against High-temperature requirement A, and modifications to the C-7 position of the 3-alkoxy-4-chloroisocoumarin structure affected anti-chlamydial properties. The compounds were found to be inactive against Chlamydia pecorum. Separately, a new series of compounds based on a tricyclic isoquinoline scaffold was investigated, with activity identified against gram-positive pathogens. However, cytotoxic properties were also identified against mammalian cell lines, which may limit their potential as antibacterial agents.

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http://hdl.handle.net/10453/181127