Novel reaction products from the hypervalent iodine oxidation of hydroxylated stilbenes and isoflavones
Novel reaction products from the hypervalent iodine oxidation of hydroxylated stilbenes and isoflavones
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DOI：
10.1039/b510240e
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发表时间：
2005-11-07
影响因子：
3.2
通讯作者：
Westwell, AD
中科院分区：
文献类型：
--
作者：
Lion, CJ;Vasselin, DA;Westwell, AD
Novel reaction pathways for the hypervalent iodine-mediated oxidation of bioactive phenols containing extended conjugated pi-systems are described. Oxidation of 4-hydroxystilbenes in methanol using a hypervalent iodine-based oxidant led to the formal 1,2-addition of methoxy groups across the central stilbene double bond. Treatment of the structurally related 4-hydroxyisoflavone with di(trifluoroacetoxy)iodobenzene leads to the surprising formation of 2,4'-dihydroxybenzil. Potential mechanisms for these new reaction pathways are discussed, and the X-ray crystal structure of 2,4'-dihydroxybenzil is presented. In contrast, oxidation of the corresponding 3-hydroxystilbenes and 3-hydroxyisoflavone led to conventional dienone oxidation products. The antitumour implications of these oxidation processes are briefly highlighted; the novel 4-substituted phenolic oxidation products were found to be inactive in terms of in vitro antitumour cellular activity, whereas the 3-substituted phenol products gave novel agents with potent and enhanced antitumour activity in the HCT 116 cancer cell line.
