Please use this identifier to cite or link to this item: https://hdl.handle.net/10356/103024
Title: 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
Authors: Susanti, Dewi
Liu, Li-Juan
Rao, Weidong
Lin, Sheng
Ma, Dik-Lung
Leung, Chung-Hang
Chan, Philip Wai Hong
Keywords: DRNTU::Science::Chemistry::Physical chemistry::Catalysis
Issue Date: 2015
Source: Susanti, D., Liu, L.-J., Rao, W., Lin, S., Ma, D.-L., Leung, C. H., et al. (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.
Series/Report no.: Chemistry - a European journal
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.
URI: https://hdl.handle.net/10356/103024
http://hdl.handle.net/10220/25763
ISSN: 0947-6539
DOI: 10.1002/chem.201500795
Rights: © 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
Fulltext Permission: none
Fulltext Availability: No Fulltext
Appears in Collections:SPMS Journal Articles

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