3-bromo-octaacetyldiosmin | 827346-24-7

• 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: 3-bromo-octaacetyldiosmin
• 英文别名: 3-bromooctacetyldiosmin
• CAS: 827346-24-7
• 化学式: C₄₄H₄₇BrO₂₃
• 分子量: 1023.75
• InChiKey: FXZQBKGEMMASGG-GTJJGJLJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.54
• 重原子数：
  68.0
• 可旋转键数：
  15.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  286.76
• 氢给体数：
  0.0
• 氢受体数：
  23.0

反应信息

• 作为反应物：
  描述：

  3-bromo-octaacetyldiosmin 在 盐酸 、 potassium hydrogencarbonate 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.5h， 生成 3-bromodiosmetin 7,3'-dibenzyl ether
  参考文献：
  名称：

  Synthesis and anti-tubulin evaluation of chromone-based analogues of combretastatins

  摘要：

  Twenty new hybrid compounds with both combretastatin and flavone moieties were synthesized. These derivatives are classified according to the position of the trimethoxyphenyl ring at C-2 or C-3 of the chromone and presence or absence of a carbonyl as a linker between C-3 and the aryl ring. Most of these compounds were prepared from hesperidin or naringin, two natural and abundant Citrus flavonoids. Seven of these combretastatin analogues revealed anti-tubulin activity but in a medium range. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.02.024
• 作为产物：
  描述：

  地奥司明八乙酸酯 在 吡啶 、 N-溴代丁二酰亚胺(NBS) 作用下， 以 二氯甲烷 为溶剂， 反应 20.0h， 以90%的产率得到3-bromo-octaacetyldiosmin
  参考文献：
  名称：

  Synthesis and anti-tubulin evaluation of chromone-based analogues of combretastatins

  摘要：

  Twenty new hybrid compounds with both combretastatin and flavone moieties were synthesized. These derivatives are classified according to the position of the trimethoxyphenyl ring at C-2 or C-3 of the chromone and presence or absence of a carbonyl as a linker between C-3 and the aryl ring. Most of these compounds were prepared from hesperidin or naringin, two natural and abundant Citrus flavonoids. Seven of these combretastatin analogues revealed anti-tubulin activity but in a medium range. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.02.024

文献信息

• Enhancement of the Water Solubility of Flavone Glycosides by Disruption of Molecular Planarity of the Aglycone Moiety
  作者：Guy Lewin、Alexandre Maciuk、Aurélien Moncomble、Jean-Paul Cornard

  DOI：10.1021/np300460a

  日期：2013.1.25

  Enhancement of the water solubility by disruption of molecular planarity has recently been reviewed as a feasible approach in small-molecule drug discovery programs. We applied this strategy to some natural flavone glycosides, especially diosmin, a highly insoluble citroflavonoid prescribed as an oral phlebotropic drug. Disruption of planarity at the aglycone moiety by 3-bromination or chlorination

  最近，通过破坏分子平面性来增强水溶性的方法已被认为是小分子药物发现计划中的一种可行方法。我们将此策略应用于某些天然黄酮苷，尤其是薯os皂素，这是一种高度不溶的柠檬黄酮类药物，被指定为口服降血糖药。通过3-溴化或氯化破坏糖苷配基部分的平面度，得到3-溴-和3-氯二恶英，与母体化合物相比，溶解度显着增加。