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dc.contributor.authorKumar, Rohiteshen_US
dc.contributor.authorC. Sadowski, Martinen_US
dc.contributor.authorLevrier, Claireen_US
dc.contributor.authorC. Nelson, Colleenen_US
dc.contributor.authorJones, Amyen_US
dc.contributor.authorHolleran, Johnen_US
dc.contributor.authorAvery, Vickyen_US
dc.contributor.authorHealy, Peteren_US
dc.contributor.authorDavis, Rohanen_US
dc.date.accessioned2017-05-03T12:36:27Z
dc.date.available2017-05-03T12:36:27Z
dc.date.issued2015en_US
dc.identifier.issn0163-3864en_US
dc.identifier.doi10.1021/np500856uen_US
dc.identifier.urihttp://hdl.handle.net/10072/101062
dc.description.abstractThe fungal metabolite 3-chloro-4-hydroxyphenylacetic acid (1) was utilized in the generation of a unique drug-like screening library using parallel solution-phase synthesis. A 20-membered amide library (3–22) was generated by first converting 1 to methyl (3-chloro-4-hydroxyphenyl)acetate (2), then reacting this scaffold with a diverse series of primary amines via a solvent-free aminolysis procedure. The structures of the synthetic analogues (3–22) were elucidated by spectroscopic data analysis. The structures of compounds 8, 12, and 22 were confirmed by single X-ray crystallographic analysis. All compounds were evaluated for cytotoxicity against a human prostate cancer cell line (LNCaP) and for antiparasitic activity toward Trypanosoma brucei brucei and Plasmodium falciparum and showed no significant activity at 10 μM. The library was also tested for effects on the lipid content of LNCaP and PC-3 prostate cancer cells, and it was demonstrated that the fluorobenzyl analogues (12–14) significantly reduced cellular phospholipid and neutral lipid levels.en_US
dc.description.peerreviewedYesen_US
dc.languageEnglishen_US
dc.publisherAmerican Chemical Societyen_US
dc.relation.ispartofpagefrom914en_US
dc.relation.ispartofpageto918en_US
dc.relation.ispartofissue4en_US
dc.relation.ispartofjournalJournal of Natural Productsen_US
dc.relation.ispartofvolume78en_US
dc.subject.fieldofresearchChemical Sciences not elsewhere classifieden_US
dc.subject.fieldofresearchcode039999en_US
dc.titleDesign and synthesis of a screening library using the natural product scaffold 3-chloro-4-hydroxyphenylacetic aciden_US
dc.typeJournal articleen_US
dc.type.descriptionC1 - Peer Reviewed (HERDC)en_US
dc.type.codeC - Journal Articlesen_US
dc.description.versionPublisheden_US
gro.facultyGriffith Sciences, Griffith Institute for Drug Discoveryen_US
gro.rights.copyright© 2015 American Chemical Society and American Society of Pharmacognosy. This is an open access article published under an ACS AuthorChoice License, which permits copying and redistribution of the article or any adaptations for non-commercial purposes.en_US
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