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
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...
| Main Authors: | , , , , , , |
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| Format: | Journal Article |
| Language: | English |
| Published: |
2015
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| Online Access: | https://hdl.handle.net/10356/103024 http://hdl.handle.net/10220/25763 |
| _version_ | 1811691374383202304 |
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| author | Susanti, Dewi Liu, Li-Juan Rao, Weidong Lin, Sheng Ma, Dik-Lung Leung, Chung-Hang Chan, Philip Wai Hong |
| author2 | School of Physical and Mathematical Sciences |
| author_facet | School of Physical and Mathematical Sciences Susanti, Dewi Liu, Li-Juan Rao, Weidong Lin, Sheng Ma, Dik-Lung Leung, Chung-Hang Chan, Philip Wai Hong |
| author_sort | Susanti, Dewi |
| collection | NTU |
| description | 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. |
| first_indexed | 2024-10-01T06:18:52Z |
| format | Journal Article |
| id | ntu-10356/103024 |
| institution | Nanyang Technological University |
| language | English |
| last_indexed | 2024-10-01T06:18:52Z |
| publishDate | 2015 |
| record_format | dspace |
| spelling | ntu-10356/1030242020-03-07T12:34:41Z 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, Dewi Liu, Li-Juan Rao, Weidong Lin, Sheng Ma, Dik-Lung Leung, Chung-Hang Chan, Philip Wai Hong School of Physical and Mathematical Sciences DRNTU::Science::Chemistry::Physical chemistry::Catalysis 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. 2015-06-04T09:02:34Z 2019-12-06T21:04:08Z 2015-06-04T09:02:34Z 2019-12-06T21:04:08Z 2015 2015 Journal Article 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. 0947-6539 https://hdl.handle.net/10356/103024 http://hdl.handle.net/10220/25763 10.1002/chem.201500795 en Chemistry - a European journal © 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim. |
| spellingShingle | DRNTU::Science::Chemistry::Physical chemistry::Catalysis Susanti, Dewi Liu, Li-Juan Rao, Weidong Lin, Sheng Ma, Dik-Lung Leung, Chung-Hang Chan, Philip Wai Hong 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 |
| 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 |
| title_full | 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 |
| title_fullStr | 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 |
| title_full_unstemmed | 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 |
| title_short | 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 |
| title_sort | 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 |
| topic | DRNTU::Science::Chemistry::Physical chemistry::Catalysis |
| url | https://hdl.handle.net/10356/103024 http://hdl.handle.net/10220/25763 |
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