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dc.contributor.authorKumar, Rohitesh
dc.contributor.authorSadowski, Martin C
dc.contributor.authorLevrier, Claire
dc.contributor.authorNelson, Colleen C
dc.contributor.authorJones, Amy J
dc.contributor.authorHolleran, John P
dc.contributor.authorAvery, Vicky M
dc.contributor.authorHealy, Peter C
dc.contributor.authorDavis, Rohan A
dc.date.accessioned2017-05-03T12:36:27Z
dc.date.available2017-05-03T12:36:27Z
dc.date.issued2015
dc.identifier.issn0163-3864
dc.identifier.doi10.1021/np500856u
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.
dc.description.peerreviewedYes
dc.languageEnglish
dc.publisherAmerican Chemical Society
dc.relation.ispartofpagefrom914
dc.relation.ispartofpageto918
dc.relation.ispartofissue4
dc.relation.ispartofjournalJournal of Natural Products
dc.relation.ispartofvolume78
dc.subject.fieldofresearchChemical Sciences not elsewhere classified
dc.subject.fieldofresearchBiological Sciences
dc.subject.fieldofresearchMedical and Health Sciences
dc.subject.fieldofresearchChemical Sciences
dc.subject.fieldofresearchcode039999
dc.subject.fieldofresearchcode06
dc.subject.fieldofresearchcode11
dc.subject.fieldofresearchcode03
dc.titleDesign and synthesis of a screening library using the natural product scaffold 3-chloro-4-hydroxyphenylacetic acid
dc.typeJournal article
dc.type.descriptionC1 - Articles
dc.type.codeC - Journal Articles
dc.description.versionPublished
gro.facultyGriffith Sciences, Griffith Institute for Drug Discovery
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.
gro.hasfulltextFull Text
gro.griffith.authorHealy, Peter C.
gro.griffith.authorDavis, Rohan A.
gro.griffith.authorAvery, Vicky M.
gro.griffith.authorJones, Amy J.
gro.griffith.authorLevrier, Claire
gro.griffith.authorKumar, Rohitesh
gro.griffith.authorHolleran, John


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