dimethyl 2-[1-phenyl-(E)-ethylidene]succinate | 58266-36-7

• 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: dimethyl 2-[1-phenyl-(E)-ethylidene]succinate
• 英文别名: ((E)-1-phenyl-ethylidene)-succinic acid dimethyl ester；((E)-1-Phenyl-aethyliden)-bernsteinsaeure-dimethylester
• CAS: 58266-36-7
• 化学式: C₁₄H₁₆O₄
• 分子量: 248.279
• InChiKey: BMNKDEBPVWUNRO-ZRDIBKRKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 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：
  0.29
• 拓扑面积：
  52.6
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  dimethyl 2-[1-phenyl-(E)-ethylidene]succinate 、 3,4,5-三甲氧基苯甲醛 在 potassium tert-butylate 、 叔丁醇 作用下， 反应 1.0h， 以78%的产率得到(E)-2-((E)-3-methoxy-3-oxo-1-(3,4,5-trimethoxyphenyl)prop-1-en-2-yl)-3-phenylbut-2-enoic acid
  参考文献：
  名称：

  Design, synthesis, and evaluation of orally active inhibitors of plasminogen activator inhibitor-1 (PAI-1) production

  摘要：

  A novel series of butadiene-imide 1 (T-686) derivatives having an inhibitory activity against PAI-1 production was synthesized and evaluated their biological activities and DMPK profiles, in which 15k (T-2639) was selected as the best compound based on its strong antithrombotic activity and good bioavailability. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.10.067
• 作为产物：
  描述：

  甲醇 、 2-[1-Phenyl-eth-(E)-ylidene]-succinic acid 1-methyl ester 在 氯化亚砜 作用下， 反应 16.0h， 生成 dimethyl 2-[1-phenyl-(E)-ethylidene]succinate
  参考文献：
  名称：

  Design, synthesis, and evaluation of orally active inhibitors of plasminogen activator inhibitor-1 (PAI-1) production

  摘要：

  A novel series of butadiene-imide 1 (T-686) derivatives having an inhibitory activity against PAI-1 production was synthesized and evaluated their biological activities and DMPK profiles, in which 15k (T-2639) was selected as the best compound based on its strong antithrombotic activity and good bioavailability. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.10.067

文献信息

• Synthesis and evaluation of 1,4-diphenylbutadiene derivatives as inhibitors of plasminogen activator inhibitor-1 (PAI-1) production
  作者：Hiroshi Miyazaki、Hiroshi Sai、Hiroshi Ohmizu、Jun Murakami、Akio Ohtani、Tsuyoshi Ogiku

  DOI：10.1016/j.bmc.2010.01.032

  日期：2010.3

  antithrombotic activity in two rat thrombosis models without affecting bleeding time, indicating reduction of haemorrhagic risk. We also describe in this report a practical synthesis of 15k suitable for scale-up using Z,E-selective Stobbe condensation.

  合成了丁二烯酰亚胺1（T-686）衍生物，并评估了其对PAI-1产生的抑制活性及其ADMET（DMPK和毒理学）特性。在这些衍生物中，化合物15k（T-2639）在两个大鼠血栓形成模型中显示出良好的抗血栓形成活性，而不会影响出血时间，表明出血风险降低。我们还在本报告中描述了适用于使用Z，E选择性Stobbe缩合放大的15k实用合成方法。