(2E,6E)-7-(3,4-dimethoxyphenyl)-4-((E)-3-(3,4-dimethoxyphenyl)acryloyl)-5-oxohepta-2,6-dienamide | 1118765-37-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二芳基庚烷
• 英文名称: (2E,6E)-7-(3,4-dimethoxyphenyl)-4-((E)-3-(3,4-dimethoxyphenyl)acryloyl)-5-oxohepta-2,6-dienamide
• 英文别名: (2E,6E)-7-(3,4-dimethoxyphenyl)-4-[(E)-3-(3,4-dimethoxyphenyl)prop-2-enoyl]-5-oxohepta-2,6-dienamide
• CAS: 1118765-37-9
• 化学式: C₂₆H₂₇NO₇
• 分子量: 465.503
• InChiKey: WPHOZGMQHYTTLT-MRWVPCFPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  34
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  114
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (2E,6E)-7-(3,4-dimethoxyphenyl)-4-((E)-3-(3,4-dimethoxyphenyl)acryloyl)-5-oxohepta-2,6-dienamide 在 盐酸肼 、 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 40.0h， 以84%的产率得到(E,E,E)-3-(3,5-bis(3,4-dimethoxystyryl)-1H-pyrazol-4-yl)acrylamide
  参考文献：
  名称：

  Synthesis and evaluation of electron-rich curcumin analogues

  摘要：

  The natural product curcumin has long been recognized for its medicinal properties and is utilized for the treatment of many diseases. However, it remains unknown whether this activity is based on its presumably promiscuous scaffold, or if it results from the Michael acceptor properties of the alpha,beta-unsaturated 1,3-diketone moiety central to its structure. To probe this issue, electron-rich pyrazole and isoxazole analogues were prepared and evaluated against two breast cancer cell lines, which resulted in the identification of several compounds that exhibit low micromolar to mid nanomolar anti-proliferative activity. A conjugate addition study was also performed to compare the relative electrophilicity of the diketone, pyrazole and isoxazole analogues. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.10.057
• 作为产物：
  描述：

  丙炔酰胺 、 二甲氧基姜黄素 在 sodium hydride 作用下， 以 四氢呋喃 、 mineral oil 为溶剂， 反应 24.67h， 以88%的产率得到(2E,6E)-7-(3,4-dimethoxyphenyl)-4-((E)-3-(3,4-dimethoxyphenyl)acryloyl)-5-oxohepta-2,6-dienamide
  参考文献：
  名称：

  Synthesis and evaluation of electron-rich curcumin analogues

  摘要：

  The natural product curcumin has long been recognized for its medicinal properties and is utilized for the treatment of many diseases. However, it remains unknown whether this activity is based on its presumably promiscuous scaffold, or if it results from the Michael acceptor properties of the alpha,beta-unsaturated 1,3-diketone moiety central to its structure. To probe this issue, electron-rich pyrazole and isoxazole analogues were prepared and evaluated against two breast cancer cell lines, which resulted in the identification of several compounds that exhibit low micromolar to mid nanomolar anti-proliferative activity. A conjugate addition study was also performed to compare the relative electrophilicity of the diketone, pyrazole and isoxazole analogues. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.10.057

文献信息

• Synthesis and evaluation of electron-rich curcumin analogues
  作者：Michael W. Amolins、Laura B. Peterson、Brian S.J. Blagg

  DOI：10.1016/j.bmc.2008.10.057

  日期：2009.1

  The natural product curcumin has long been recognized for its medicinal properties and is utilized for the treatment of many diseases. However, it remains unknown whether this activity is based on its presumably promiscuous scaffold, or if it results from the Michael acceptor properties of the alpha,beta-unsaturated 1,3-diketone moiety central to its structure. To probe this issue, electron-rich pyrazole and isoxazole analogues were prepared and evaluated against two breast cancer cell lines, which resulted in the identification of several compounds that exhibit low micromolar to mid nanomolar anti-proliferative activity. A conjugate addition study was also performed to compare the relative electrophilicity of the diketone, pyrazole and isoxazole analogues. (C) 2008 Elsevier Ltd. All rights reserved.