1-(4-Hydroxy-3,5-dimethoxyphenyl)-7-(4-hydroxy-3-methoxyphenyl)-(1E,6E)-1,6-heptadiene-3,4-dione | 144761-33-1

• 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: 1-(4-Hydroxy-3,5-dimethoxyphenyl)-7-(4-hydroxy-3-methoxyphenyl)-(1E,6E)-1,6-heptadiene-3,4-dione
• 英文别名: 5'-methoxycurcumin；5′-methoxycurcumin；(1E,6E)-1-(4-hydroxy-3,5-dimethoxyphenyl)-7-(4-hydroxy-3-methoxyphenyl)hepta-1,6-diene-3,5-dione
• CAS: 144761-33-1
• 化学式: C₂₂H₂₂O₇
• 分子量: 398.412
• InChiKey: MQJGAHXKAZGEGI-NSLJXJERSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  29
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  102
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  1-(4-Hydroxy-3,5-dimethoxyphenyl)-7-(4-hydroxy-3-methoxyphenyl)-(1E,6E)-1,6-heptadiene-3,4-dione 在 吡啶 、 三氯化铝 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 36.0h， 以55%的产率得到(1E,6E)-1-(3,4-Dihydroxy-5-methoxy-phenyl)-7-(3,4-dihydroxy-phenyl)-hepta-1,6-diene-3,5-dione
  参考文献：
  名称：

  Synthesis and biological evaluation of polyhydroxycurcuminoids

  摘要：

  A series of curcurnin analogs (1-3, 5a-5t) was synthesized through the condensation of appropriately protected hydroxy-benzaldehydes with acetylacetone, followed by deprotection. The antioxidant activity of these analogs was determined by superoxide free radical nitroblue tetrazolium and DPPH free radical scavenging methods and the polyhydroxycurcuminoids (5l-5s) displayed excellent antioxidant activity. These analogs showed cytotoxicity to lymphocytes and promising tumor-reducing activity on Dalton's lymphoma ascites tumor cells. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.06.050
• 作为产物：
  描述：

  香草醛 、 乙酰丙酮 、 丁香醛 在 boron trioxide 、 硼酸三丁酯 、 1,2,3,4-四氢喹啉 、 溶剂黄146 作用下， 以 N,N-二甲基甲酰胺 、 水 为溶剂， 反应 5.25h， 以16%的产率得到1-(4-Hydroxy-3,5-dimethoxyphenyl)-7-(4-hydroxy-3-methoxyphenyl)-(1E,6E)-1,6-heptadiene-3,4-dione
  参考文献：
  名称：

  Synthesis and biological evaluation of polyhydroxycurcuminoids

  摘要：

  A series of curcurnin analogs (1-3, 5a-5t) was synthesized through the condensation of appropriately protected hydroxy-benzaldehydes with acetylacetone, followed by deprotection. The antioxidant activity of these analogs was determined by superoxide free radical nitroblue tetrazolium and DPPH free radical scavenging methods and the polyhydroxycurcuminoids (5l-5s) displayed excellent antioxidant activity. These analogs showed cytotoxicity to lymphocytes and promising tumor-reducing activity on Dalton's lymphoma ascites tumor cells. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.06.050

文献信息

• Modulation of peroxisome proliferator-activated receptors
  申请人：Lin Rong-Hwa

  公开号：US20070037193A1

  公开（公告）日：2007-02-15

  A method of treating a peroxisome proliferators-activated receptors related disease by administering to a subject in need thereof an effective amount of a modulator of 15-keto prostaglandin-Δ 13 -reductase. Also disclosed are methods of identifying a compound for inhibiting activity of the reductase and of lowering blood glucose levels by administering to a subject an effective amount of a reductase inhibitor.
• Synthesis and biological evaluation of polyhydroxycurcuminoids
  作者：Somepalli Venkateswarlu、Marellapudi S. Ramachandra、Gottumukkala V. Subbaraju

  DOI：10.1016/j.bmc.2005.06.050

  日期：2005.12

  A series of curcurnin analogs (1-3, 5a-5t) was synthesized through the condensation of appropriately protected hydroxy-benzaldehydes with acetylacetone, followed by deprotection. The antioxidant activity of these analogs was determined by superoxide free radical nitroblue tetrazolium and DPPH free radical scavenging methods and the polyhydroxycurcuminoids (5l-5s) displayed excellent antioxidant activity. These analogs showed cytotoxicity to lymphocytes and promising tumor-reducing activity on Dalton's lymphoma ascites tumor cells. (c) 2005 Elsevier Ltd. All rights reserved.