(3R,9bS)-3-benzyl-2,3-dihydro-9b-methyloxazolo[2,3-a]-isoindol-5(9bH)-one | 1431509-16-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: (3R,9bS)-3-benzyl-2,3-dihydro-9b-methyloxazolo[2,3-a]-isoindol-5(9bH)-one
• 英文别名: (3r,9Bs)-3-benzyl-2,3-dihydro-9b-methyloxazolo[2,3-a]isoindol-5(9bh)-one；(3R,9bS)-3-benzyl-9b-methyl-2,3-dihydro-[1,3]oxazolo[2,3-a]isoindol-5-one
• CAS: 1431509-16-8
• 化学式: C₁₈H₁₇NO₂
• 分子量: 279.338
• InChiKey: IGMVFNBADVJBSA-KDOFPFPSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-乙酰苯甲酸 、 D-苯丙氨醇 以 甲苯 为溶剂， 反应 16.0h， 以85%的产率得到(3R,9bS)-3-benzyl-2,3-dihydro-9b-methyloxazolo[2,3-a]-isoindol-5(9bH)-one
  参考文献：
  名称：

  Synthesis of phenylalaninol-derived oxazolopyrrolidone lactams and evaluation as NMDA receptor antagonists

  摘要：

  N-Methyl-d-aspartate (NMDA) receptor antagonists are known to rescue neuronal cell death caused by excessive activation of glutamate receptors. This phenomenon, known as excitotoxicity, is implicated in the pathogenesis of several neurodegenerative disorders including ischemia, Alzheimer's disease, Parkinson's disease, and Huntington's disease. Unfortunately, some NMDA receptor antagonists have shown discouraging results when tested in clinical trials. However, recent advances in the physiology and pharmacology of the NMDA receptor have kept interest alive in modulating NMDA receptors for therapeutic intervention. We present here the synthesis of a small library of phenylalaninol-derived oxazolopyrrolidone lactams and their evaluation as NMDA receptor antagonists. The compounds were easily synthesized in yields up to 92 %. In addition, one of the compounds has a 50 % inhibitory concentration (IC (50)) of 62 mu M and offers potential to develop more potent NMDA receptor antagonists.

  DOI：

  10.1007/s00706-012-0880-8

文献信息

• Synthesis of phenylalaninol-derived oxazolopyrrolidone lactams and evaluation as NMDA receptor antagonists
  作者：Nuno A. L. Pereira、Francesc X. Sureda、Mireia Turch、Mercedes Amat、Joan Bosch、Maria M. M. Santos

  DOI：10.1007/s00706-012-0880-8

  日期：2013.4

  N-Methyl-d-aspartate (NMDA) receptor antagonists are known to rescue neuronal cell death caused by excessive activation of glutamate receptors. This phenomenon, known as excitotoxicity, is implicated in the pathogenesis of several neurodegenerative disorders including ischemia, Alzheimer's disease, Parkinson's disease, and Huntington's disease. Unfortunately, some NMDA receptor antagonists have shown discouraging results when tested in clinical trials. However, recent advances in the physiology and pharmacology of the NMDA receptor have kept interest alive in modulating NMDA receptors for therapeutic intervention. We present here the synthesis of a small library of phenylalaninol-derived oxazolopyrrolidone lactams and their evaluation as NMDA receptor antagonists. The compounds were easily synthesized in yields up to 92 %. In addition, one of the compounds has a 50 % inhibitory concentration (IC (50)) of 62 mu M and offers potential to develop more potent NMDA receptor antagonists.