Collective synthesis of 4-hydroxy-2-pyridone alkaloids and their antiproliferation activities
A collective synthesis of 4-hydroxy-2-pyridone alkaloids—specifically, pretenellin B, prebassianin B, farinosone A, militarione D, pyridovericin, and torrubiellone C—has been achieved. Key steps include using a strategic convergent method to synthesize the densely substituted pyridone key intermedia...
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| Format: | Journal Article |
| Language: | English |
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2014
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| Online Access: | https://hdl.handle.net/10356/105141 http://hdl.handle.net/10220/20459 http://dx.doi.org/10.1002/asia.201402466 |
| _version_ | 1826127358130651136 |
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| author | Ding, Feiqing Leow, Min Li Ma, Jimei William, Ronny Liao, Hongze Liu, Xue-Wei |
| author2 | School of Physical and Mathematical Sciences |
| author_facet | School of Physical and Mathematical Sciences Ding, Feiqing Leow, Min Li Ma, Jimei William, Ronny Liao, Hongze Liu, Xue-Wei |
| author_sort | Ding, Feiqing |
| collection | NTU |
| description | A collective synthesis of 4-hydroxy-2-pyridone alkaloids—specifically, pretenellin B, prebassianin B, farinosone A, militarione D, pyridovericin, and torrubiellone C—has been achieved. Key steps include using a strategic convergent method to synthesize the densely substituted pyridone key intermediate by Suzuki–Miyaura cross-coupling reaction, a divergent synthesis approach of target molecules by aldol condensation of pyridone intermediate with homologous aldehydes, and an iterative synthesis of homologous aldehydes with all-trans-polyene backbones. Interestingly, among the six tumor cell lines investigated, torrubiellone C was found to induce potent and apoptotic inhibitory activities on Jurkat T cells with IC50 values of 7.05 μm. Hence, this approach could potentially contribute to the synthesis of bioactive small-molecule libraries as well as drug discovery. |
| first_indexed | 2024-10-01T07:07:35Z |
| format | Journal Article |
| id | ntu-10356/105141 |
| institution | Nanyang Technological University |
| language | English |
| last_indexed | 2024-10-01T07:07:35Z |
| publishDate | 2014 |
| record_format | dspace |
| spelling | ntu-10356/1051412019-12-06T21:46:28Z Collective synthesis of 4-hydroxy-2-pyridone alkaloids and their antiproliferation activities Ding, Feiqing Leow, Min Li Ma, Jimei William, Ronny Liao, Hongze Liu, Xue-Wei School of Physical and Mathematical Sciences DRNTU::Science::Chemistry A collective synthesis of 4-hydroxy-2-pyridone alkaloids—specifically, pretenellin B, prebassianin B, farinosone A, militarione D, pyridovericin, and torrubiellone C—has been achieved. Key steps include using a strategic convergent method to synthesize the densely substituted pyridone key intermediate by Suzuki–Miyaura cross-coupling reaction, a divergent synthesis approach of target molecules by aldol condensation of pyridone intermediate with homologous aldehydes, and an iterative synthesis of homologous aldehydes with all-trans-polyene backbones. Interestingly, among the six tumor cell lines investigated, torrubiellone C was found to induce potent and apoptotic inhibitory activities on Jurkat T cells with IC50 values of 7.05 μm. Hence, this approach could potentially contribute to the synthesis of bioactive small-molecule libraries as well as drug discovery. 2014-09-08T07:59:03Z 2019-12-06T21:46:28Z 2014-09-08T07:59:03Z 2019-12-06T21:46:28Z 2014 2014 Journal Article Ding, F., Leow, M. L., Ma, J., William, R., Liao, H., & Liu, X.-W. (2014). Collective synthesis of 4-hydroxy-2-pyridone alkaloids and their antiproliferation activities. Chemistry - An Asian journal, 9(9), 2548-2554. 1861-4728 https://hdl.handle.net/10356/105141 http://hdl.handle.net/10220/20459 http://dx.doi.org/10.1002/asia.201402466 en Chemistry - An Asian journal © 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim. |
| spellingShingle | DRNTU::Science::Chemistry Ding, Feiqing Leow, Min Li Ma, Jimei William, Ronny Liao, Hongze Liu, Xue-Wei Collective synthesis of 4-hydroxy-2-pyridone alkaloids and their antiproliferation activities |
| title | Collective synthesis of 4-hydroxy-2-pyridone alkaloids and their antiproliferation activities |
| title_full | Collective synthesis of 4-hydroxy-2-pyridone alkaloids and their antiproliferation activities |
| title_fullStr | Collective synthesis of 4-hydroxy-2-pyridone alkaloids and their antiproliferation activities |
| title_full_unstemmed | Collective synthesis of 4-hydroxy-2-pyridone alkaloids and their antiproliferation activities |
| title_short | Collective synthesis of 4-hydroxy-2-pyridone alkaloids and their antiproliferation activities |
| title_sort | collective synthesis of 4 hydroxy 2 pyridone alkaloids and their antiproliferation activities |
| topic | DRNTU::Science::Chemistry |
| url | https://hdl.handle.net/10356/105141 http://hdl.handle.net/10220/20459 http://dx.doi.org/10.1002/asia.201402466 |
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