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Gold-catalyzed cycloisomerization and diels-alder reaction of 1,4,9-dienyne esters to 3 a,6-methanoisoindole esters with pro-inflammatory cytokine antagonist activity
Susanti D.3; Liu L.-J.5; Rao W.3; Lin S.2; Ma D.-L.2; Leung C.-H.5; Chan P.W.H.1,3,4
2015-06-01
Source PublicationChemistry - A European Journal
ISSN15213765 09476539
Volume21Issue:25Pages:9111-9118
Abstract

A synthetic method to prepare 3a,6-methanoisoindole esters efficiently by gold(I)-catalyzed tandem 1,2-acyloxy migration/Nazarov cyclization followed by Diels-Alder reaction of 1,4,9-dienyne esters is described. We also report the ability of one example to inhibit binding of tumor necrosis factor-α (TNF-α) to the tumor necrosis factor receptor 1 (TNFR1) site and TNF-α-induced nuclear factor κ-light-chain-enhancer of activated B cells (NF-κB) activation in cell at a half-maximal inhibitory concentration (IC50) value of 6.6 μM. Along with this is a study showing the isoindolyl derivative to exhibit low toxicity toward human hepatocellular liver carcinoma (HepG2) cells and its possible mode of activity based on molecular modeling analysis. A synthetic method to prepare 3a,6-methanoisoindole esters efficiently by gold(I)-catalyzed tandem 1,2-acyloxy migration/Nazarov cyclization/Diels-Alder reaction of 1,4,9-dienyne esters is described (see scheme). The ability of one example to exhibit potent pro-inflammatory cytokine antagonist activity along with low cytotoxicity and its possible mode of bioactivity is also presented.

KeywordAlkynes Cycloisomerization Cytokine Antagonists Gold Homogeneous Catalysis
DOI10.1002/chem.201500795
URLView the original
Indexed BySCIE ; IC
Language英语
WOS Research AreaChemistry
WOS SubjectChemistry, Multidisciplinary
WOS IDWOS:000355762900023
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Cited Times [WOS]:29   [WOS Record]     [Related Records in WOS]
Document TypeJournal article
CollectionInstitute of Chinese Medical Sciences
Affiliation1.Monash University
2.Hong Kong Baptist University
3.Nanyang Technological University
4.The University of Warwick
5.University of Macau
Recommended Citation
GB/T 7714
Susanti D.,Liu L.-J.,Rao W.,et al. Gold-catalyzed cycloisomerization and diels-alder reaction of 1,4,9-dienyne esters to 3 a,6-methanoisoindole esters with pro-inflammatory cytokine antagonist activity[J]. Chemistry - A European Journal,2015,21(25):9111-9118.
APA Susanti D.,Liu L.-J.,Rao W.,Lin S.,Ma D.-L.,Leung C.-H.,&Chan P.W.H..(2015).Gold-catalyzed cycloisomerization and diels-alder reaction of 1,4,9-dienyne esters to 3 a,6-methanoisoindole esters with pro-inflammatory cytokine antagonist activity.Chemistry - A European Journal,21(25),9111-9118.
MLA Susanti D.,et al."Gold-catalyzed cycloisomerization and diels-alder reaction of 1,4,9-dienyne esters to 3 a,6-methanoisoindole esters with pro-inflammatory cytokine antagonist activity".Chemistry - A European Journal 21.25(2015):9111-9118.
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