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dc.contributor.authorZhang, Wenhanen_US
dc.contributor.authorChu, Jenniferen_US
dc.contributor.authorCyr, Andrew M.en_US
dc.contributor.authorYueh, Hanen_US
dc.contributor.authorBrown, Lauren E.en_US
dc.contributor.authorWang, Tony T.en_US
dc.contributor.authorPelletier, Jerryen_US
dc.contributor.authorPorco, John A.en_US
dc.coverage.spatialUnited Statesen_US
dc.date.accessioned2020-09-04T14:18:07Z
dc.date.available2020-09-04T14:18:07Z
dc.date.issued2019-08-14
dc.identifierhttps://www.ncbi.nlm.nih.gov/pubmed/31310112
dc.identifier.citationWenhan Zhang, Jennifer Chu, Andrew M Cyr, Han Yueh, Lauren E Brown, Tony T Wang, Jerry Pelletier, John A Porco. 2019. "Intercepted Retro-Nazarov Reaction: Syntheses of Amidino-Rocaglate Derivatives and Their Biological Evaluation as eIF4A Inhibitors.." J Am Chem Soc, Volume 141, Issue 32, pp. 12891 - 12900. https://doi.org/10.1021/jacs.9b06446
dc.identifier.issn1520-5126
dc.identifier.urihttps://hdl.handle.net/2144/41373
dc.descriptionPublished in final edited form as: J Am Chem Soc. 2019 August 14; 141(32): 12891–12900. doi:10.1021/jacs.9b06446.en_US
dc.description.abstractRocaglates are a family of natural products isolated from the genus Aglaia which possess a highly substituted cyclopenta[b]benzofuran skeleton and inhibit cap-dependent protein synthesis. Rocaglates are attractive compounds due to their potential for inhibiting tumor cell maintenance in vivo by specifically targeting eukaryotic initiation factor 4A (eIF4A) and interfering with recruitment of ribosomes to mRNA. In this paper, we describe an intercepted retro-Nazarov reaction utilizing intramolecular tosyl migration to generate a reactive oxyallyl cation on the rocaglate skeleton. Trapping of the oxyallyl cation with a diverse range of nucleophiles has been used to generate over 50 novel amidino-rocaglate (ADR) and amino-rocaglate derivatives. Subsequently, these derivatives were evaluated for their ability to inhibit cap-dependent protein synthesis where they were found to outperform previous lead compounds including the rocaglate hydroxamate CR-1-31-B.en_US
dc.description.sponsorshipP50 GM067041 - NIGMS NIH HHS; R01 DK088787 - NIDDK NIH HHS; R35 GM118173 - NIGMS NIH HHS; FDN-148366 - CIHRen_US
dc.format.extentp. 12891 - 12900en_US
dc.languageeng
dc.language.isoen_US
dc.relation.ispartofJ Am Chem Soc
dc.subjectGeneral chemistryen_US
dc.subjectChemical sciencesen_US
dc.titleIntercepted retro-Nazarov reaction: syntheses of amidino-rocaglate derivatives and their biological evaluation as eIF4A inhibitorsen_US
dc.typeArticleen_US
dc.description.versionAccepted manuscripten_US
dc.identifier.doi10.1021/jacs.9b06446
pubs.elements-sourcepubmeden_US
pubs.notesEmbargo: Not knownen_US
pubs.organisational-groupBoston Universityen_US
pubs.organisational-groupBoston University, College of Arts & Sciencesen_US
pubs.organisational-groupBoston University, College of Arts & Sciences, Department of Chemistryen_US
pubs.publication-statusPublisheden_US
dc.identifier.mycv483057


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