3-[3-(isoindolin-2-yl)propyl]benzoxazolin-2-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并恶唑类
• 英文名称: 3-[3-(isoindolin-2-yl)propyl]benzoxazolin-2-one
• 英文别名: 3-[3-(1,3-Dihydroisoindol-2-yl)propyl]-1,3-benzoxazol-2-one；3-[3-(1,3-dihydroisoindol-2-yl)propyl]-1,3-benzoxazol-2-one
• 化学式: C₁₈H₁₈N₂O₂
• 分子量: 294.353
• InChiKey: QFKLXDXOJBQTLG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  32.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  异吲哚啉 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 24.5h， 生成 3-[3-(isoindolin-2-yl)propyl]benzoxazolin-2-one
  参考文献：
  名称：

  Synthesis and pharmacological evaluation of benzannulated derivatives as potent and selective sigma-1 protein ligands

  摘要：

  The sigma(1) proteins are considered to be a new class of target structures for several central nervous system disorders, including depression, anxiety, psychosis, and Parkinson's and Alzheimer's diseases. Recently, the involvement of these receptors in neuropathic pain and cancer has also been observed. So far, only a few ligands are in clinical trials. In a continuation of our previous studies on the development of sigma(1) ligands, a new series of benzannulated heterocycles was designed and synthesised. In vitro competition binding assays showed that many of them possessed high cri receptor affinity (K-i = 0.6-10.3 nM), and good sigma(2)/sigma(1) subtype selectivity, without cytotoxic effects on SY5Y cells (human neuroblastoma cell line). (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.01.013