- Collective synthesis of 4-hydroxy-2-pyridone alkaloids and their antiproliferation activities
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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.
- Ding, Feiqing,Leow, Min Li,Ma, Jimei,William, Ronny,Liao, Hongze,Liu, Xue-Wei
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supporting information
p. 2548 - 2554
(2014/10/15)
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- Practical Pd/C-catalysed suzuki-miyaura reactions for the preparation of 3-aryl-4-oxypyridin-2(1H)-ones, 3-aryl-2,4-oxypyridines and 3-aryl-2,4- oxyquinolines as useful intermediates for the synthesis of biologically active compounds
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Practical heterogeneous Pd/C-catalysed Suzuki-Miyaura cross-coupling reactions of 3-iodo-4-oxypyridin-2(1H)-ones, 3-iodo-2,4-oxypyridines, and 3-iodo-2,4-oxyquinolines with arylboronic acids are described as a useful and efficient alternative to homogeneous conditions. The methodology features ligand-free and environmentally friendly conditions, and tolerates a wide range of boronic acids. The cross-coupled products can be viewed as useful intermediates for the preparation of 3-aryl-4-hydroxypyridin-2(1H)-ones, which can be used as new nucleobases for antiherpetic agents.
- Lamblin, Marc,Bares, Hugo,Dessolin, Jean,Marty, Christel,Bourgougnon, Nathalie,Felpin, Francois-Xavier
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p. 5525 - 5533
(2012/10/29)
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- Total synthesis of (±)-cordypyridones A and B and related epimers
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"Chemical Equation Presented" Efficient racemic synthesis of two antibacterial and antimalarial natural products, cordypyridones A and B, was achieved from inexpensive, commercially available starting materials In an overall yield of 15% (8% and 7%, respe
- Jones, Ian L.,Moore, Felicity K.,Chai, Christina L. L.
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supporting information; experimental part
p. 5526 - 5529
(2010/02/28)
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- A practical 2,3-pyridyne precursor
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3-Bromo-2-chloro-4-methoxypyridine has been developed as a practical 2,3-pyridine precursor. The substituted 2,3-pyridine generated from this precursor by halogen-metal exchange has been found to react regioselectively with 2-methoxyfuran and 2-methylfuran.
- Walters,Carter,Banerjee
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p. 2829 - 2837
(2007/10/02)
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