Z-ethyl 2-(hydroxy(o-chlorophenyl)methylene)-3-oxobutanoate | 119031-27-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: Z-ethyl 2-(hydroxy(o-chlorophenyl)methylene)-3-oxobutanoate
• CAS: 119031-27-5
• 化学式: C₁₃H₁₃ClO₄
• 分子量: 268.697
• InChiKey: BRKNEDWVHCJYNR-QXMHVHEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.76
• 重原子数：
  18.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  63.6
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  Z-ethyl 2-(hydroxy(o-chlorophenyl)methylene)-3-oxobutanoate 在 肼 作用下， 以 乙醇 为溶剂， 反应 19.0h， 以79%的产率得到ethyl 3-(o-chlorophenyl)-5-methyl-1H-pyrazole-4-carboxylate
  参考文献：
  名称：

  Synthesis and discovery of a novel pyrazole derivative as an inhibitor of apoptosis through modulating integrin β4, ROS, and p53 levels in vascular endothelial cells

  摘要：

  Recently, pyrazole derivatives as high affinity and selective A2A adenosine receptor antagonists have been reported. But, so far, there are no reports about the inhibitory effects of multi-substituted pyrazole derivatives on apoptosis of vascular endothelial cells (VECs). In this study, we synthesized six pyrazole derivatives and characterized the structures of the compounds by IR, H-1 NMR, mass spectroscopy, and element analysis. The biology assay showed that a novel pyrazole derivative, ethyl 3-(o-chlorophenyl)-5- methyl-1-phenyl-1H-pyrazole-4-carboxylate (MPD) at low concentration (25 mu M) increased VECs viability and inhibited VECs apoptosis induced by deprivation of serum and FGF-2. During this process, the levels of integrin beta 4, reactive oxygen species (ROS), and p53 were depressed obviously. The data suggested that MPD was a potential inhibitor of apoptosis associated with the signal pathway mediated by integrin beta 4, ROS, and p53 in VECs. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.03.011
• 作为产物：
  描述：

  乙酰乙酸乙酯 、 邻氯苯甲酰氯 在 sodium hydroxide 作用下， 以 Petroleum ether 为溶剂， 反应 2.0h， 以61%的产率得到Z-ethyl 2-(hydroxy(o-chlorophenyl)methylene)-3-oxobutanoate
  参考文献：
  名称：

  Synthesis and discovery of a novel pyrazole derivative as an inhibitor of apoptosis through modulating integrin β4, ROS, and p53 levels in vascular endothelial cells

  摘要：

  Recently, pyrazole derivatives as high affinity and selective A2A adenosine receptor antagonists have been reported. But, so far, there are no reports about the inhibitory effects of multi-substituted pyrazole derivatives on apoptosis of vascular endothelial cells (VECs). In this study, we synthesized six pyrazole derivatives and characterized the structures of the compounds by IR, H-1 NMR, mass spectroscopy, and element analysis. The biology assay showed that a novel pyrazole derivative, ethyl 3-(o-chlorophenyl)-5- methyl-1-phenyl-1H-pyrazole-4-carboxylate (MPD) at low concentration (25 mu M) increased VECs viability and inhibited VECs apoptosis induced by deprivation of serum and FGF-2. During this process, the levels of integrin beta 4, reactive oxygen species (ROS), and p53 were depressed obviously. The data suggested that MPD was a potential inhibitor of apoptosis associated with the signal pathway mediated by integrin beta 4, ROS, and p53 in VECs. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.03.011