(1E,4Z,6E)-5-hydroxy-1,7-bis(4-(4-methylpiperazin-1-yl)phenyl)hepta-1,4,6-trien-3-one

• 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: (1E,4Z,6E)-5-hydroxy-1,7-bis(4-(4-methylpiperazin-1-yl)phenyl)hepta-1,4,6-trien-3-one
• 英文别名: (1E,4Z,6E)-5-hydroxy-1,7-bis[4-(4-methylpiperazin-1-yl)phenyl]hepta-1,4,6-trien-3-one
• 化学式: C₂₉H₃₆N₄O₂
• 分子量: 472.63
• InChiKey: KOFRWDMLZOLYGQ-XIIKBWDRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  35
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.34
• 拓扑面积：
  50.3
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl 2-(bromomethyl)-3-phenylacrylate 、 (1E,4Z,6E)-5-hydroxy-1,7-bis(4-(4-methylpiperazin-1-yl)phenyl)hepta-1,4,6-trien-3-one 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 以41%的产率得到
  参考文献：
  名称：

  Synthesis, in vitro, and in vivo evaluation of novel functionalized quaternary ammonium curcuminoids as potential anti-cancer agents

  摘要：

  Novel functionalized quaternary ammonium curcuminoids have been synthesized from piperazinyl curcuminoids and Baylis-Hillman reaction derived allyl bromides. These molecules are found to be highly water soluble with increased cytotoxicity compared to native curcumin against three cancer cell lines MIAPaCa-2, MDA-MB-231, and 4T1. Preliminary in vivo toxicity evaluation of a representative curcuminoid 5a in healthy mice indicates that this molecule is well tolerated based on normal body weight gains compared to control group. Furthermore, the efficacy of 5a has been tested in a pancreatic cancer xenograft model of MIAPaCa-2 and has been found to exhibit good tumor growth inhibition as a single agent and also in combination with clinical pancreatic cancer drug gemcitabine. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2015.10.061
• 作为产物：
  描述：

  N-甲基哌嗪 在 boron trioxide 、 potassium carbonate 作用下， 以 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 反应 14.5h， 生成 (1E,4Z,6E)-5-hydroxy-1,7-bis(4-(4-methylpiperazin-1-yl)phenyl)hepta-1,4,6-trien-3-one
  参考文献：
  名称：

  Synthesis, in vitro, and in vivo evaluation of novel functionalized quaternary ammonium curcuminoids as potential anti-cancer agents

  摘要：

  Novel functionalized quaternary ammonium curcuminoids have been synthesized from piperazinyl curcuminoids and Baylis-Hillman reaction derived allyl bromides. These molecules are found to be highly water soluble with increased cytotoxicity compared to native curcumin against three cancer cell lines MIAPaCa-2, MDA-MB-231, and 4T1. Preliminary in vivo toxicity evaluation of a representative curcuminoid 5a in healthy mice indicates that this molecule is well tolerated based on normal body weight gains compared to control group. Furthermore, the efficacy of 5a has been tested in a pancreatic cancer xenograft model of MIAPaCa-2 and has been found to exhibit good tumor growth inhibition as a single agent and also in combination with clinical pancreatic cancer drug gemcitabine. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2015.10.061

文献信息

• Synthesis, in vitro, and in vivo evaluation of novel functionalized quaternary ammonium curcuminoids as potential anti-cancer agents
  作者：Lucas N. Solano、Grady L. Nelson、Conor T. Ronayne、Erica A. Lueth、Melissa A. Foxley、Sravan K. Jonnalagadda、Shirisha Gurrapu、Venkatram R. Mereddy

  DOI：10.1016/j.bmcl.2015.10.061

  日期：2015.12

  Novel functionalized quaternary ammonium curcuminoids have been synthesized from piperazinyl curcuminoids and Baylis-Hillman reaction derived allyl bromides. These molecules are found to be highly water soluble with increased cytotoxicity compared to native curcumin against three cancer cell lines MIAPaCa-2, MDA-MB-231, and 4T1. Preliminary in vivo toxicity evaluation of a representative curcuminoid 5a in healthy mice indicates that this molecule is well tolerated based on normal body weight gains compared to control group. Furthermore, the efficacy of 5a has been tested in a pancreatic cancer xenograft model of MIAPaCa-2 and has been found to exhibit good tumor growth inhibition as a single agent and also in combination with clinical pancreatic cancer drug gemcitabine. (C) 2015 Elsevier Ltd. All rights reserved.