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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
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Susanti, Dewi, Liu, Li-Juan, Rao, Weidong, Lin, Sheng, Ma, Dik-Lung, Leung, Chung-Hang and Chan, Philip Wai Hong (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). pp. 9111-9118. doi:10.1002/chem.201500795 ISSN 0947-6539.
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Official URL: http://dx.doi.org/10.1002/chem.201500795
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.
Item Type: | Journal Article | ||||||||||||
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Subjects: | Q Science > QD Chemistry | ||||||||||||
Divisions: | Faculty of Science, Engineering and Medicine > Science > Chemistry | ||||||||||||
Library of Congress Subject Headings (LCSH): | Esters, Catalysis, Diels-Alder reaction, Cytokines | ||||||||||||
Journal or Publication Title: | Chemistry - A European Journal | ||||||||||||
Publisher: | Wiley - V C H Verlag GmbH & Co. KGaA | ||||||||||||
ISSN: | 0947-6539 | ||||||||||||
Official Date: | June 2015 | ||||||||||||
Dates: |
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Volume: | 21 | ||||||||||||
Number: | 25 | ||||||||||||
Page Range: | pp. 9111-9118 | ||||||||||||
DOI: | 10.1002/chem.201500795 | ||||||||||||
Status: | Peer Reviewed | ||||||||||||
Publication Status: | Published | ||||||||||||
Access rights to Published version: | Restricted or Subscription Access | ||||||||||||
RIOXX Funder/Project Grant: |
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