ethyl 3-[(2-morpholin-4-yl)ethyl]aminopropenoate

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: ethyl 3-[(2-morpholin-4-yl)ethyl]aminopropenoate
• 英文别名: ethyl (Z)-3-(2-morpholin-4-ylethylamino)but-2-enoate
• 化学式: C₁₂H₂₂N₂O₃
• 分子量: 242.318
• InChiKey: BPYNRZLQZDYJLW-KHPPLWFESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  17
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  50.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl 3-[(2-morpholin-4-yl)ethyl]aminopropenoate 在 sodium hydride 作用下， 以 四氢呋喃 、 硝基甲烷 为溶剂， 反应 50.75h， 生成 ethyl 5-methoxy-1-[(2-morpholin-4-yl)ethyl]-2,6-dimethylindole-3-carboxylate
  参考文献：
  名称：

  Indolequinone Antitumor Agents:  Correlation between Quinone Structure and Rate of Metabolism by Recombinant Human NAD(P)H:Quinone Oxidoreductase. Part 2

  摘要：

  A series of indolequinones bearing various functional groups has been synthesized, and the effects of substituents on the metabolism of the quinones. by recombinant human NAD(P)H: quinone oxidoreductase (NQO1) were studied. Indolequinones were selected for study on the basis of the X-ray crystal structure of the human enzyme, and were designed to probe the effect of substituents particularly at N-1. Metabolism of the quinones. by NQO1 revealed that, in general, compounds with electron-withdrawing groups at the indole 3-position were among the best substrates, and that groups larger than methyl at N-1 are clearly tolerated. Compounds with a leaving group at the 3-indolyl methyl position generally inactivated the enzyme. The toxicity toward human colon carcinoma cells with either no detectable activity (BE-WT) or high NQO1 activity (BE-NQ) was also studied in representative quinones. The most toxic compounds were those with a leaving group at the C-3 position; these compounds were 1.1-5.3-fold more toxic. to the BE-NQ than the BE-WT cells.

  DOI：

  10.1021/jm010884c

文献信息

• Process for preparation of substituted dihydropyridines and intermediates therefor
  申请人：USV PHARMACEUTICAL CORPORATION

  公开号：EP0109049A2

  公开（公告）日：1984-05-23

  The invention provides, a new process for preparing dihydropyridines useful in the treatment of hypertension.

  本发明提供了一种用于制备治疗高血压的二氢吡啶类化合物的新工艺。
• US4497808A
  申请人：——

  公开号：US4497808A

  公开（公告）日：1985-02-05
• Indolequinone Antitumor Agents:  Correlation between Quinone Structure and Rate of Metabolism by Recombinant Human NAD(P)H:Quinone Oxidoreductase. Part 2
  作者：Elizabeth Swann、Paola Barraja、Ann M. Oberlander、Walter T. Gardipee、Anna R. Hudnott、Howard D. Beall、Christopher J. Moody

  DOI：10.1021/jm010884c

  日期：2001.9.1

  A series of indolequinones bearing various functional groups has been synthesized, and the effects of substituents on the metabolism of the quinones. by recombinant human NAD(P)H: quinone oxidoreductase (NQO1) were studied. Indolequinones were selected for study on the basis of the X-ray crystal structure of the human enzyme, and were designed to probe the effect of substituents particularly at N-1. Metabolism of the quinones. by NQO1 revealed that, in general, compounds with electron-withdrawing groups at the indole 3-position were among the best substrates, and that groups larger than methyl at N-1 are clearly tolerated. Compounds with a leaving group at the 3-indolyl methyl position generally inactivated the enzyme. The toxicity toward human colon carcinoma cells with either no detectable activity (BE-WT) or high NQO1 activity (BE-NQ) was also studied in representative quinones. The most toxic compounds were those with a leaving group at the C-3 position; these compounds were 1.1-5.3-fold more toxic. to the BE-NQ than the BE-WT cells.