7-geranoxy-5-hydroxyflavone

• 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: 7-geranoxy-5-hydroxyflavone
• 英文别名: 7-O-Geranylchrysin；7-[(2E)-3,7-dimethylocta-2,6-dienoxy]-5-hydroxy-2-phenylchromen-4-one
• 化学式: C₂₅H₂₆O₄
• 分子量: 390.479
• InChiKey: XORKBYTZZUAVOH-LDADJPATSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  29
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  7-geranoxy-5-hydroxyflavone 在 sodium acetate 、 乙酸酐 、 氢氧化钾 作用下， 以 甲醇 为溶剂， 反应 73.0h， 以49%的产率得到8-Linalylchrysin
  参考文献：
  名称：

  Effects of Flavonoids on Cell Proliferation and Caspase Activation in a Human Colonic Cell Line HT29:  An SAR Study

  摘要：

  A library of 42 natural and synthetic flavonoids has been screened for their effect on cell proliferation and apoptosis in a human colonic cell line (HT-29). Examples of different classes of flavonoids have been screened, and the effects of hydroxylation, methoxylation and/or C-alkylation at various positions in the A- and B-rings have been assessed. Flavones and flavonols possess greater antiproliferative activity than chalcones and flavanones. With respect to structural modification of flavonoids, C-isoprenylation was by far the most effective, with substitution at the 8-position and longer chains, such as geranyl giving the best results. Finally, most compounds that significantly reduced cell survival also increased caspase activity, suggesting that at least part of their antiproliferative activity might be attributable to an apoptotic response.

  DOI：

  10.1021/jm040770b
• 作为产物：
  描述：

  香叶基溴 、 白杨素 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 生成 7-geranoxy-5-hydroxyflavone
  参考文献：
  名称：

  新型7- O-亲脂性黄ba素衍生物作为潜在抗癌药的合成及生物学评估†

  摘要：

  我们通过在具有亲脂性三联苯或长链正烷基的A环的7- O位上进行烷基化反应，合成了黄ical素，沃戈宁和菊花链素的衍生物，并通过生长抑制MTT分析研究了这些衍生物的体外抗癌活性。我们发现黄ical素及其两个衍生物是良好的自由基清除剂。在20种合成衍生物中，与黄ical苷相比，7- O-法呢基黄ical苷（5d）和7- O-十二烷基黄ical苷（5i）对人结肠癌SW480细胞具有更强的生长抑制作用，最大抑制浓度为一半（IC 50）值分别为1.15和1.57μM。此外，5d和5i剂量和时间依赖性抑制SW480细胞的生长。细胞周期分布分析表明5d和5i通过凋亡机制诱导SW480细胞停滞在S期，这与活性氧的产生增加有关。总之，黄ical素衍生物（5d和5i）的有效抗癌活性表明，这些衍生物是潜在的人类结肠癌抗癌药。

  DOI：

  10.1039/c5md00163c

文献信息

• Effects of Flavonoids on Cell Proliferation and Caspase Activation in a Human Colonic Cell Line HT29:  An SAR Study
  作者：Jean-Baptiste Daskiewicz、Flore Depeint、Lionel Viornery、Christine Bayet、Geraldine Comte-Sarrazin、Gilles Comte、Jennifer M. Gee、Ian T. Johnson、Karine Ndjoko、Kurt Hostettmann、Denis Barron

  DOI：10.1021/jm040770b

  日期：2005.4.1

  A library of 42 natural and synthetic flavonoids has been screened for their effect on cell proliferation and apoptosis in a human colonic cell line (HT-29). Examples of different classes of flavonoids have been screened, and the effects of hydroxylation, methoxylation and/or C-alkylation at various positions in the A- and B-rings have been assessed. Flavones and flavonols possess greater antiproliferative activity than chalcones and flavanones. With respect to structural modification of flavonoids, C-isoprenylation was by far the most effective, with substitution at the 8-position and longer chains, such as geranyl giving the best results. Finally, most compounds that significantly reduced cell survival also increased caspase activity, suggesting that at least part of their antiproliferative activity might be attributable to an apoptotic response.
• Synthesis and biological evaluation of novel 7-O-lipophilic substituted baicalein derivatives as potential anticancer agents
  作者：Shao-Hung Wang、Ching-Hsein Chen、Chih-Yu Lo、Ji-Zhen Feng、Hong-Jhih Lin、Po-Ya Chang、Ling-Ling Yang、Lih-Geeng Chen、Yi-Wen Liu、Cheng-Deng Kuo、Jin-Yi Wu

  DOI：10.1039/c5md00163c

  日期：——

  We synthesized derivatives of baicalein, wogonin, and chrysin through alkylation at the 7-O-position of the A ring with lipophilic terphenyl or long chain n-alkyl groups, and studied the in vitro anticancer activity of the derivatives through the growth inhibition MTT assay. We discovered that baicalein and two of its derivatives were good free radical scavengers. Among the 20 synthesized derivatives

  我们通过在具有亲脂性三联苯或长链正烷基的A环的7- O位上进行烷基化反应，合成了黄ical素，沃戈宁和菊花链素的衍生物，并通过生长抑制MTT分析研究了这些衍生物的体外抗癌活性。我们发现黄ical素及其两个衍生物是良好的自由基清除剂。在20种合成衍生物中，与黄ical苷相比，7- O-法呢基黄ical苷（5d）和7- O-十二烷基黄ical苷（5i）对人结肠癌SW480细胞具有更强的生长抑制作用，最大抑制浓度为一半（IC 50）值分别为1.15和1.57μM。此外，5d和5i剂量和时间依赖性抑制SW480细胞的生长。细胞周期分布分析表明5d和5i通过凋亡机制诱导SW480细胞停滞在S期，这与活性氧的产生增加有关。总之，黄ical素衍生物（5d和5i）的有效抗癌活性表明，这些衍生物是潜在的人类结肠癌抗癌药。