(E)-5-(4-hydroxy-3-methoxyphenyl)-1-(4-hydroxyphenyl)pent-4-ene-1,3-dione | 1449290-08-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (E)-5-(4-hydroxy-3-methoxyphenyl)-1-(4-hydroxyphenyl)pent-4-ene-1,3-dione
• CAS: 1449290-08-7
• 化学式: C₁₈H₁₆O₅
• 分子量: 312.322
• InChiKey: MTSVXXUYSZWHIW-QHHAFSJGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.96
• 重原子数：
  23.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  83.83
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (E)-5-(4-hydroxy-3-methoxyphenyl)-1-(4-hydroxyphenyl)pent-4-ene-1,3-dione 在 一水合肼 、 溶剂黄146 作用下， 以81%的产率得到(E)-4-(2-(5-(4-hydroxyphenyl)-1H-pyrazol-3-yl)vinyl)-2-methoxyphenol
  参考文献：
  名称：

  Synthesis and tubulin-binding properties of non-symmetrical click C5-curcuminoids

  摘要：

  A click-type entry into shortened curcuminoids of the diarylpentanoid type has been developed. The reaction is ideally suited to generate non-symmetrical analogues of curcumin, a class of natural products difficult to access but of growing biomedical relevance and special mechanistic interest to investigate the unique binding mode of curcumin to tubulin. Investigation of a series of click diarylpentane curcuminoids and their pyrazole adducts in various cellular tubulin functional assays validated this class of compounds as a novel type of anti-mitotic agents, evidencing structure-activity relationships, and identifying the pyrazole adduct 4k as a promising lead. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.05.053
• 作为产物：
  描述：

  p-Hydroxybenzoylaceton 、 香草醛 在 boron trioxide 、 硼酸三甲酯 、 正丁胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以40%的产率得到(E)-5-(4-hydroxy-3-methoxyphenyl)-1-(4-hydroxyphenyl)pent-4-ene-1,3-dione
  参考文献：
  名称：

  Synthesis and tubulin-binding properties of non-symmetrical click C5-curcuminoids

  摘要：

  A click-type entry into shortened curcuminoids of the diarylpentanoid type has been developed. The reaction is ideally suited to generate non-symmetrical analogues of curcumin, a class of natural products difficult to access but of growing biomedical relevance and special mechanistic interest to investigate the unique binding mode of curcumin to tubulin. Investigation of a series of click diarylpentane curcuminoids and their pyrazole adducts in various cellular tubulin functional assays validated this class of compounds as a novel type of anti-mitotic agents, evidencing structure-activity relationships, and identifying the pyrazole adduct 4k as a promising lead. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.05.053