1-allyl-1H-pyrrole-3-carboxaldehyde

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-allyl-1H-pyrrole-3-carboxaldehyde
• 英文别名: 1-Prop-2-enylpyrrole-3-carbaldehyde
• 化学式: C₈H₉NO
• 分子量: 135.166
• InChiKey: ANCRTEUGVAHUOU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  10
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  22
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-allyl-1H-pyrrole-3-carboxaldehyde 在 正丁基锂 、 叠氮磷酸二苯酯 、 sodium 、 silver nitrate 、 三乙胺 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 二氯甲烷 、 苯 为溶剂， 反应 2.0h， 生成 (5R)-5-(methoxymethyl)-3-(1-prop-2-enylpyrrol-3-yl)-1,3-oxazolidin-2-one
  参考文献：
  名称：

  Novel Reversible Monoamine Oxidase A Inhibitors: Highly Potent and Selective 3-(1H-Pyrrol-3-yl)-2-oxazolidinones

  摘要：

  Monoamine oxidases (MAOs) are involved in various psychiatric and neurodegenerative disorders; hence, MAO inhibitors are useful agents in the therapy of Parkinson's disease, Alzheimer's dementia, and depression syndrome. Herein we report a novel series of 3-(1H-pyrrol-3-yl)-2-oxazolidinones 3-7 as reversible, highly potent and selective anti-MAO-A agents. In particular, 4b, 5b, and 4c showed a Ki-MAO-A of 0.6, 0.8, and I nM, respectively, 4c being 200000-fold selective for MAO-A with respect to MAO-B.

  DOI：

  10.1021/jm201011x
• 作为产物：
  描述：

  吡咯-3-甲醛 、 3-溴丙烯 在 potassium hydroxide 作用下， 以 二甲基亚砜 为溶剂， 反应 4.83h， 以84%的产率得到1-allyl-1H-pyrrole-3-carboxaldehyde
  参考文献：
  名称：

  Novel Reversible Monoamine Oxidase A Inhibitors: Highly Potent and Selective 3-(1H-Pyrrol-3-yl)-2-oxazolidinones

  摘要：

  Monoamine oxidases (MAOs) are involved in various psychiatric and neurodegenerative disorders; hence, MAO inhibitors are useful agents in the therapy of Parkinson's disease, Alzheimer's dementia, and depression syndrome. Herein we report a novel series of 3-(1H-pyrrol-3-yl)-2-oxazolidinones 3-7 as reversible, highly potent and selective anti-MAO-A agents. In particular, 4b, 5b, and 4c showed a Ki-MAO-A of 0.6, 0.8, and I nM, respectively, 4c being 200000-fold selective for MAO-A with respect to MAO-B.

  DOI：

  10.1021/jm201011x

文献信息

• Synthesis and biological evaluation of enantiomerically pure pyrrolyl-oxazolidinones as a new class of potent and selective monoamine oxidase type A inhibitors
  作者：A. Mai、Marino Artico、M. Esposito、R. Ragno、G. Sbardella、S. Massa

  DOI：10.1016/s0014-827x(03)00016-8

  日期：2003.3

  Due to the key role played by monoamine oxidases (MAOs) in the metabolism of neurotransmitters, MAO inhibitors (MAOIs) represent an useful tool for the treatment of several neurological diseases. Among selective MAOIs, MAO-A inhibitors (e.g. clorgyline) are used as antidepressant and antianxiety drugs and are claimed to protect neuronal cells against apoptosis, and selective MAO-B inhibitors (e.g. L-deprenyl) can be used in the treatment of Parkinson's disease either alone or in combination with L-DOPA. However, they engender covalent bonds with the active site of the enzyme and induce irreversible inhibition; moreover, they tend to lose their initial selectivity at high dosages or with repeated administrations. Phenyloxazolidinones belong to third-generation-MAOIs, characterized by a selective and reversible inhibition of the enzyme. Among these molecules, the most representative are toloxatone and befloxatone, two selective and reversible MAO-A inhibitors used in therapy as antidepressant drugs. Going on our searches on CNS potentially active compounds containing a pyrrole moiety we prepared 3-(1H-pyrrol-1-yl)-2-oxazolidinones (1) and isomeric 3-(1H-pyrrol-2-and -3-yl)-2-oxazolidinones (2 and 3) as anti-MAO agents. Such derivatives resulted selective and reversible MAO-A inhibitors. The most potent compound is (R)-5-methoxymethyl-3-(1H-pyrrol-1-yl)-2-oxazolidinone (1b), endowed with very high potency (K(iMAO-A) = 4.9 nM) and A-selectivity (A-selectivity = 10,200, about 116-fold greater than that of befloxatone).
• Novel Reversible Monoamine Oxidase A Inhibitors: Highly Potent and Selective 3-(1<i>H</i>-Pyrrol-3-yl)-2-oxazolidinones
  作者：Sergio Valente、Stefano Tomassi、Giampiero Tempera、Stefania Saccoccio、Enzo Agostinelli、Antonello Mai

  DOI：10.1021/jm201011x

  日期：2011.12.8

  Monoamine oxidases (MAOs) are involved in various psychiatric and neurodegenerative disorders; hence, MAO inhibitors are useful agents in the therapy of Parkinson's disease, Alzheimer's dementia, and depression syndrome. Herein we report a novel series of 3-(1H-pyrrol-3-yl)-2-oxazolidinones 3-7 as reversible, highly potent and selective anti-MAO-A agents. In particular, 4b, 5b, and 4c showed a Ki-MAO-A of 0.6, 0.8, and I nM, respectively, 4c being 200000-fold selective for MAO-A with respect to MAO-B.