Synthesis and biological evaluation of 7-O-modified oroxylin A derivatives

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Abstract

Oroxylin A (5,7-dihydroxy-6-methoxyflavone) is a naturally occurring monoflavonoid isolated from the root of Scutellaria baicalensis Georgi, and exhibits potent anticancer activities in vitro and in vivo. In this study, we synthesized three series of oroxylin derivatives by connecting a nitrogen-containing hydrophilic, heterocyclic ring to the C7-OH via a varying length of carbon chain. All the derivatives were screened for anti-proliferative activities against three tumor cell lines. Some of the derivatives displayed higher activities compared to oroxylin A. The most potent antitumor compound, 5f, also induced apoptosis in HepG2 cell. The difference of 5f between the inhibiting rates of cell proliferation and the apoptotic rates indicated that 5f was more likely to be a necrosis-inducing agent or both apoptosis/necrosis inducer. © 2011 Elsevier Ltd. All rights reserved.

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Fu, W., Wang, J., Yu, L., Zhao, L., Lu, N., You, Q., … Li, Z. (2012). Synthesis and biological evaluation of 7-O-modified oroxylin A derivatives. Bioorganic and Medicinal Chemistry Letters, 22(2), 1118–1121. https://doi.org/10.1016/j.bmcl.2011.11.117

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