5-Hydroxy-6-methoxy-7-(4-morpholin-4-ylbutoxy)-2-phenylchromen-4-one | 1263323-19-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 英文名称: 5-Hydroxy-6-methoxy-7-(4-morpholin-4-ylbutoxy)-2-phenylchromen-4-one
• CAS: 1263323-19-8
• 化学式: C₂₄H₂₇NO₆
• 分子量: 425.481
• InChiKey: LPDFRNKWRSVFGF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  31
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  77.5
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  千层纸素A 在 potassium carbonate 作用下， 以 丙酮 、 乙腈 为溶剂， 生成 5-Hydroxy-6-methoxy-7-(4-morpholin-4-ylbutoxy)-2-phenylchromen-4-one
  参考文献：
  名称：

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

  摘要：

  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 Sf was more likely to be a necrosis-inducing agent or both apoptosis/necrosis inducer. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.11.117

文献信息

• Synthesis and biological evaluation of 7-O-modified oroxylin A derivatives
  作者：Wei Fu、Jubo Wang、Liqin Yu、Li Zhao、Na Lu、Qidong You、Qinglong Guo、Zhiyu Li

  DOI：10.1016/j.bmcl.2011.11.117

  日期：2012.1

  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 Sf was more likely to be a necrosis-inducing agent or both apoptosis/necrosis inducer. (C) 2011 Elsevier Ltd. All rights reserved.