4-Chloroisocoumarins as Chlamydial Protease Inhibitors and Anti-Chlamydial Agents.

Phillips, MJA; Huston, WM; McDonagh, AM; Rawling, T

4-Chloroisocoumarins as Chlamydial Protease Inhibitors and Anti-Chlamydial Agents.

Phillips, MJA Huston, WM McDonagh, AM Rawling, T

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Publisher:: MDPI
Publication Type:: Journal Article
Citation:: Molecules, 2024, 29, (7), pp. 1519
Issue Date:: 2024-03-28

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Field	Value	Language
dc.contributor.author	Phillips, MJA
dc.contributor.author	Huston, WM
dc.contributor.author	McDonagh, AM
dc.contributor.author	Rawling, T https://orcid.org/0000-0002-6624-6586
dc.date.accessioned	2024-08-02T02:42:03Z
dc.date.available	2024-03-26
dc.date.available	2024-08-02T02:42:03Z
dc.date.issued	2024-03-28
dc.identifier.citation	Molecules, 2024, 29, (7), pp. 1519
dc.identifier.issn	1420-3049
dc.identifier.issn	1420-3049
dc.identifier.uri	http://hdl.handle.net/10453/179994
dc.description.abstract	4-Chloroisocoumarin compounds have broad inhibitory properties against serine proteases. Here, we show that selected 3-alkoxy-4-chloroisocoumarins preferentially inhibit the activity of the conserved serine protease High-temperature requirement A of Chlamydia trachomatis. The synthesis of a new series of isocoumarin-based scaffolds has been developed, and their anti-chlamydial properties were investigated. The structure of the alkoxy substituent was found to influence the potency of the compounds against High-temperature requirement A, and modifications to the C-7 position of the 3-alkoxy-4-chloroisocoumarin structure attenuate anti-chlamydial properties.
dc.format	Electronic
dc.language	eng
dc.publisher	MDPI
dc.relation.ispartof	Molecules
dc.relation.isbasedon	10.3390/molecules29071519
dc.rights	info:eu-repo/semantics/restrictedAccess
dc.subject	0304 Medicinal and Biomolecular Chemistry, 0305 Organic Chemistry, 0307 Theoretical and Computational Chemistry
dc.subject.classification	Organic Chemistry
dc.subject.classification	3404 Medicinal and biomolecular chemistry
dc.subject.classification	3405 Organic chemistry
dc.subject.mesh	Protease Inhibitors
dc.subject.mesh	Chlamydia trachomatis
dc.subject.mesh	Enzyme Therapy
dc.subject.mesh	Isocoumarins
dc.subject.mesh	Serine Endopeptidases
dc.subject.mesh	Serine Proteases
dc.subject.mesh	Alcohols
dc.subject.mesh	Chlamydia trachomatis
dc.subject.mesh	Alcohols
dc.subject.mesh	Serine Endopeptidases
dc.subject.mesh	Protease Inhibitors
dc.subject.mesh	Isocoumarins
dc.subject.mesh	Serine Proteases
dc.subject.mesh	Enzyme Therapy
dc.subject.mesh	Protease Inhibitors
dc.subject.mesh	Chlamydia trachomatis
dc.subject.mesh	Enzyme Therapy
dc.subject.mesh	Isocoumarins
dc.subject.mesh	Serine Endopeptidases
dc.subject.mesh	Serine Proteases
dc.subject.mesh	Alcohols
dc.title	4-Chloroisocoumarins as Chlamydial Protease Inhibitors and Anti-Chlamydial Agents.
dc.type	Journal Article
utslib.citation.volume	29
utslib.location.activity	Switzerland
utslib.for	0304 Medicinal and Biomolecular Chemistry
utslib.for	0305 Organic Chemistry
utslib.for	0307 Theoretical and Computational Chemistry
pubs.organisational-group	University of Technology Sydney
pubs.organisational-group	University of Technology Sydney/Faculty of Science
pubs.organisational-group	University of Technology Sydney/Faculty of Science/School of Mathematical and Physical Sciences
pubs.organisational-group	University of Technology Sydney/Strength - CCET - Centre for Clean Energy Technology
utslib.copyright.status	recently_added	*
dc.date.updated	2024-08-02T02:41:58Z
pubs.issue	7
pubs.publication-status	Published online
pubs.volume	29
utslib.citation.issue	7

Abstract:

4-Chloroisocoumarin compounds have broad inhibitory properties against serine proteases. Here, we show that selected 3-alkoxy-4-chloroisocoumarins preferentially inhibit the activity of the conserved serine protease High-temperature requirement A of Chlamydia trachomatis. The synthesis of a new series of isocoumarin-based scaffolds has been developed, and their anti-chlamydial properties were investigated. The structure of the alkoxy substituent was found to influence the potency of the compounds against High-temperature requirement A, and modifications to the C-7 position of the 3-alkoxy-4-chloroisocoumarin structure attenuate anti-chlamydial properties.

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http://hdl.handle.net/10453/179994