3-{[ethyl-(2-hydroxyethyl)-amino]-methyl}-2,2,5,5-tetramethyl-2,5-dihydro-1H-pyrrol-1-yloxyl | 851025-44-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯啉
• 英文名称: 3-{[ethyl-(2-hydroxyethyl)-amino]-methyl}-2,2,5,5-tetramethyl-2,5-dihydro-1H-pyrrol-1-yloxyl
• CAS: 851025-44-0
• 化学式: C₁₃H₂₅N₂O₂
• 分子量: 241.354
• InChiKey: WCWIFLUEJHMGGS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.45
• 重原子数：
  17.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  46.61
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  3-{[ethyl-(2-hydroxyethyl)-amino]-methyl}-2,2,5,5-tetramethyl-2,5-dihydro-1H-pyrrol-1-yloxyl 在 盐酸 、 18-冠醚-6 、 potassium carbonate 、 三乙胺 作用下， 以 乙醇 、 二氯甲烷 、 丙酮 为溶剂， 反应 25.5h， 生成 2-butyl-3-(3,5-diiodo-4-{2-[N-ethyl,N-(1-hydroxy-2,2,5,5-tetramethyl-2,5-dihydro-1H-pyrrol-3-ylmethyl)amino]ethyl}oxybenzoyl)benzofuran dihydrochloride
  参考文献：
  名称：

  Synthesis and evaluation of the permeability transition inhibitory characteristics of paramagnetic and diamagnetic amiodarone derivatives

  摘要：

  Several amiodarone analogues were synthesized varying the 2-substituent on the benzofuran ring and diethylaminoethyl side chain of phenolether by introducing 2,2,5,5-tetramethyl-2,5-dihydro-1H-pyrrole and 1,2,5,6-tetrahydropyridine nitroxides or their amino or hydroxylamino precursors. The new compounds were screened on isolated mitochondria and perfused heart and their toxicity was evaluated on WRL-68 liver cells and H9C2 cardiomyocytes. Most of the newly synthesized derivatives exerted uncoupling effect on the mitochondrial oxidative phosphorilation at higher concentrations, compared to amiodarone and one of the modified amiodarone analogues showed an effect similar to that of arniodarone on the mitochondrial permeability transition and on restoring of mitochondrial high-energy phosphate metabolites in perfused hearts. This arniodarone analogue can be new leading compound among the experimental arniodarone analogues with the same or enhanced efficiency of amiodarone, but with less side effects. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.01.028
• 作为产物：
  描述：

  3-(bromomethyl)-2,5-dihydro-2,2,5,5-tetramethyl-1H-pyrrol-1-oxyl 、 N-乙基乙醇胺 在 potassium carbonate 作用下， 以 氯仿 为溶剂， 反应 4.0h， 以75%的产率得到3-{[ethyl-(2-hydroxyethyl)-amino]-methyl}-2,2,5,5-tetramethyl-2,5-dihydro-1H-pyrrol-1-yloxyl
  参考文献：
  名称：

  Synthesis and evaluation of the permeability transition inhibitory characteristics of paramagnetic and diamagnetic amiodarone derivatives

  摘要：

  Several amiodarone analogues were synthesized varying the 2-substituent on the benzofuran ring and diethylaminoethyl side chain of phenolether by introducing 2,2,5,5-tetramethyl-2,5-dihydro-1H-pyrrole and 1,2,5,6-tetrahydropyridine nitroxides or their amino or hydroxylamino precursors. The new compounds were screened on isolated mitochondria and perfused heart and their toxicity was evaluated on WRL-68 liver cells and H9C2 cardiomyocytes. Most of the newly synthesized derivatives exerted uncoupling effect on the mitochondrial oxidative phosphorilation at higher concentrations, compared to amiodarone and one of the modified amiodarone analogues showed an effect similar to that of arniodarone on the mitochondrial permeability transition and on restoring of mitochondrial high-energy phosphate metabolites in perfused hearts. This arniodarone analogue can be new leading compound among the experimental arniodarone analogues with the same or enhanced efficiency of amiodarone, but with less side effects. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.01.028