2-(2,5-Dihydro-1H-pyrrol-3-yl)quinoline | 918871-87-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 2-(2,5-Dihydro-1H-pyrrol-3-yl)quinoline
• CAS: 918871-87-1
• 化学式: C₁₃H₁₂N₂
• 分子量: 196.252
• InChiKey: SSSOTJBXYRJGIG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  24.9
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-溴喹啉 在 正丁基锂 、 氯化亚砜 、 氢溴酸 、 溶剂黄146 作用下， 以 乙醚 、 正己烷 为溶剂， 反应 5.0h， 生成 2-(2,5-Dihydro-1H-pyrrol-3-yl)quinoline
  参考文献：
  名称：

  Highly potent 3-pyrroline mechanism-based inhibitors of bovine plasma amine oxidase and mass spectrometric confirmation of cofactor derivatization

  摘要：

  Despite the quinone-dependent copper amine oxidases being described as having the ability to metabolize unbranched primary amines to the corresponding, aldehydes, we previously showed that the secondary amines 3-pyrrolines are metabolized as mechanism-based inactivators of bovine plasma amine oxidase (BPAO), and that the 3-(3-nitro-4-methoxyphenyl)-substituted analog was a particularly potent and efficient inactivator. We now show that additional 3-aryl-3-pyrrolines containing highly electron-withdrawing aryl groups (pyridyl, quinolyl, isoquinolyl, and pentafluorophenyl) are some of the most potent inactivators of BPAO reported to date. We also provide mass spectroscopic confirmation of the proposed mechanism of inhibition involving pyrrolylation of the active-site cofactor, through identification by MALDI-TOF and LC-ESI-MS/MS of the (3-arylpyrrol-1-yl)resorcinol derivatives of the cofactor-containing thermolytic peptides. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.11.025

文献信息

• Amine Oxidase Inhibitors
  申请人：Sayre Lawrence M.

  公开号：US20080199933A1

  公开（公告）日：2008-08-21

  A therapeutic agent for selectively inhibiting amine oxidases associated diseases and conditions in humans includes at least one compound selected from the group consisting of propargylamines, polypropargylamines, homopropargylamines, 4-substituted-2-butynylamines, 2- and 3-halloallylamines, pyrroline derivatives, cycloalkenyl branched primary amines, propargyl diamines, homopropargyl amines and diamines, allenyl amines and diamines, chloroallyl diamines, lysyne analogues, β-haloamines, RF-substituted amines, RC 1 -substituted amines, and R3Si substituted amines.
• US9161922B2
  申请人：——

  公开号：US9161922B2

  公开（公告）日：2015-10-20
• Highly potent 3-pyrroline mechanism-based inhibitors of bovine plasma amine oxidase and mass spectrometric confirmation of cofactor derivatization
  作者：Yuming Zhang、Chongzhao Ran、Guangyin Zhou、Lawrence M. Sayre

  DOI：10.1016/j.bmc.2006.11.025

  日期：2007.2

  Despite the quinone-dependent copper amine oxidases being described as having the ability to metabolize unbranched primary amines to the corresponding, aldehydes, we previously showed that the secondary amines 3-pyrrolines are metabolized as mechanism-based inactivators of bovine plasma amine oxidase (BPAO), and that the 3-(3-nitro-4-methoxyphenyl)-substituted analog was a particularly potent and efficient inactivator. We now show that additional 3-aryl-3-pyrrolines containing highly electron-withdrawing aryl groups (pyridyl, quinolyl, isoquinolyl, and pentafluorophenyl) are some of the most potent inactivators of BPAO reported to date. We also provide mass spectroscopic confirmation of the proposed mechanism of inhibition involving pyrrolylation of the active-site cofactor, through identification by MALDI-TOF and LC-ESI-MS/MS of the (3-arylpyrrol-1-yl)resorcinol derivatives of the cofactor-containing thermolytic peptides. (c) 2006 Elsevier Ltd. All rights reserved.