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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| Main Authors: | , , , , , |
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| Other Authors: | |
| Format: | Article |
| Language: | English |
| Published: |
2014
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| Subjects: | |
| Online Access: | https://hdl.handle.net/10356/105307 http://hdl.handle.net/10220/20684 http://dx.doi.org/10.1002/asia.201402466 |
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| Institution: | Nanyang Technological University |
| Language: | English |
| Summary: | 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. |
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