Total Synthesis of (±)-4,5-Bis-epi-Neovibsanin A and B: A Neurite Outgrowth Comparison Study
Total Synthesis of (±)-4,5-Bis-epi-Neovibsanin A and B: A Neurite Outgrowth Comparison Study
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DOI：
10.1021/ol901406j
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发表时间：
2009-08-20
期刊：
影响因子：
5.2
通讯作者：
Williams, Craig M.
中科院分区：
文献类型：
--
作者：
Chen, Annette P-J.;Mueller, C. Catharina;Williams, Craig M.
经12步反应合成了（+/-）-4，5-双-表-新颤藻素A和B。酸催化的一锅五步级联反应是形成三环核心的核心。天然neovibsanin A和B的两个非对映体作为理想的衍生物的构效关系研究，以探测神经营养活性。（+/-）-4，5-bis-epi-neovibsanin A和B均强烈增强NGF刺激的PC 12细胞中的神经突生长。此外，三环核心似乎在很大程度上负责促进生物反应。
(+/-)-4,5-Bis-epi-neovibsanin A and B were synthesized in 12 steps. The acid-catalyzed, one-pot, five-step cascade reaction was central toward the formation of the tricyclic core. The two diastereomers of natural neovibsanin A and B acted as desirable derivatives for structure-activity relationship studies to probe neurotrophic activity. Both (+/-)-4,5-bis-epi-neovibsanin A and B strongly potentiate neurite outgrowth in NGF-stimulated PC12 cells. Furthermore, the tricyclic core appears to be largely responsible for promoting a biological response.