10-[3-(isoindolin-2-yl)propyl]phenothiazine

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻嗪类
• 英文名称: 10-[3-(isoindolin-2-yl)propyl]phenothiazine
• 英文别名: 10-[3-(1,3-Dihydroisoindol-2-yl)propyl]phenothiazine；10-[3-(1,3-dihydroisoindol-2-yl)propyl]phenothiazine
• 化学式: C₂₃H₂₂N₂S
• 分子量: 358.507
• InChiKey: YMTQSEYVZFTIHT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  31.8
• 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 sodium hydride 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 25.0h， 生成 10-[3-(isoindolin-2-yl)propyl]phenothiazine
  参考文献：
  名称：

  Carboline- and phenothiazine-derivated heterocycles as potent SIGMA-1 protein ligands

  摘要：

  Sigma 1 receptors are associated with neurodegenerative and psychiatric disorders. These receptors, via their chaperoning functions that counteract endoplasmic reticulum stress and block neurodegeneration, may serve as a target for a new generation of antidepressants or neuroprotective agents. The involvement of these receptors has also been observed in neuropathic pain and cancer. Only a few ligands, such as Igmesine and Anavex 2-73, have been involved in clinical trials. Thus the development of sigma 1 ligands is of interest to a new generation of drugs. Previous work in our lab underlined the potency of benzannulated bicyclic compounds as interesting ligands. Herein the work was extended to a series of novel tricyclic compounds. Carboline- and phenothiazine-derivated compounds were designed and synthesized. In vitro competition binding assays for sigma 1 and 2 receptors showed that most of them have high affinity for sigma 1 receptor (K-i = 2.5-18 nM), and selectivity toward sigma 2 receptor, without cytotoxic effects on SY5Y cells. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.10.053