N-(2-(1H-pyrrol-3-yl)phenyl)-2-bromoacetamide | 1404454-94-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: N-(2-(1H-pyrrol-3-yl)phenyl)-2-bromoacetamide
• 英文别名: 2-bromo-N-[2-(1H-pyrrol-3-yl)phenyl]acetamide
• CAS: 1404454-94-9
• 化学式: C₁₂H₁₁BrN₂O
• 分子量: 279.136
• InChiKey: VSJDRWHVIIGFLY-UHFFFAOYSA-N

物化性质

• 沸点：
  463.1±35.0 °C(Predicted)
• 密度：
  1.556±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  44.9
• 氢给体数：
  2
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N-(2-(1H-pyrrol-3-yl)phenyl)-2-bromoacetamide 在 盐酸 、 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 、 1,3-二噁烷 为溶剂， 反应 24.0h， 生成 marinoquinoline A
  参考文献：
  名称：

  Biomimetic Synthesis and Biological Evaluation of Aplidiopsamine A

  摘要：

  The first total synthesis of Aplidiopsamine A, a rare 3H-pyrrolo[2,3-c]quinoline alkaloid from the Aplidiopsis confluata, has been achieved following the proposed biosynthesis. This biomimetic synthesis requires only five steps and proceeds in 20.8% overall yield. Biological evaluation across large panels of discrete molecular targets identified that Aplidiopsamine A is a highly selective PDE4 inhibitor, a target for numerous CNS disorders.

  DOI：

  10.1021/ol3024665
• 作为产物：
  描述：

  2-(1-(triisopropylsilyl)-1H-pyrrol-3-yl)aniline 在 sodium methylate 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 2.17h， 生成 N-(2-(1H-pyrrol-3-yl)phenyl)-2-bromoacetamide
  参考文献：
  名称：

  Biomimetic Synthesis and Biological Evaluation of Aplidiopsamine A

  摘要：

  The first total synthesis of Aplidiopsamine A, a rare 3H-pyrrolo[2,3-c]quinoline alkaloid from the Aplidiopsis confluata, has been achieved following the proposed biosynthesis. This biomimetic synthesis requires only five steps and proceeds in 20.8% overall yield. Biological evaluation across large panels of discrete molecular targets identified that Aplidiopsamine A is a highly selective PDE4 inhibitor, a target for numerous CNS disorders.

  DOI：

  10.1021/ol3024665

文献信息

• Biomimetic Synthesis and Biological Evaluation of Aplidiopsamine A
  作者：Joseph D. Panarese、Craig W. Lindsley

  DOI：10.1021/ol3024665

  日期：2012.11.16

  The first total synthesis of Aplidiopsamine A, a rare 3H-pyrrolo[2,3-c]quinoline alkaloid from the Aplidiopsis confluata, has been achieved following the proposed biosynthesis. This biomimetic synthesis requires only five steps and proceeds in 20.8% overall yield. Biological evaluation across large panels of discrete molecular targets identified that Aplidiopsamine A is a highly selective PDE4 inhibitor, a target for numerous CNS disorders.