1-(3-(Pyridin-3-yl)-2,5-dihydro-1H-pyrrol-1-yl)ethanone | 929083-42-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 1-(3-(Pyridin-3-yl)-2,5-dihydro-1H-pyrrol-1-yl)ethanone
• 英文别名: 1-(3-pyridin-3-yl-2,5-dihydropyrrol-1-yl)ethanone
• CAS: 929083-42-1
• 化学式: C₁₁H₁₂N₂O
• 分子量: 188.229
• InChiKey: BTHRFKSANLZSIT-UHFFFAOYSA-N

物化性质

• 沸点：
  374.8±42.0 °C(Predicted)
• 密度：
  1.178±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  33.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(3-(Pyridin-3-yl)-2,5-dihydro-1H-pyrrol-1-yl)ethanone 在 盐酸 作用下， 以 乙醇 为溶剂， 反应 3.0h， 以68.7%的产率得到3-(3-pyridyl)pyrrpline dihydrochloride
  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
• 作为产物：
  描述：

  ethyl 3-hydroxy-3-(3-pyridyl)pyrrolidine-1-carboxylate 在 氢氧化钾 、 氯化亚砜 作用下， 以 甲醇 为溶剂， 反应 52.0h， 生成 1-(3-(Pyridin-3-yl)-2,5-dihydro-1H-pyrrol-1-yl)ethanone
  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

• 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.