2-[2-[4-(6,7,8,9-tetrahydro-5H-benzo[7]annulen-5-yl)piperazin-1-yl]ethyl]isoindole-1,3-dione | 187221-92-7

• 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: 2-[2-[4-(6,7,8,9-tetrahydro-5H-benzo[7]annulen-5-yl)piperazin-1-yl]ethyl]isoindole-1,3-dione
• CAS: 187221-92-7
• 化学式: C₂₅H₂₉N₃O₂
• 分子量: 403.524
• InChiKey: DLJKXZRZQPMVCY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  30
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  43.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-[2-[4-(6,7,8,9-tetrahydro-5H-benzo[7]annulen-5-yl)piperazin-1-yl]ethyl]isoindole-1,3-dione 在 一水合肼 、 三乙胺 作用下， 以 甲醇 、 氯仿 为溶剂， 反应 4.0h， 生成 N-[2-[4-(6,7,8,9-tetrahydro-5H-benzo[7]annulen-5-yl)piperazin-1-yl]ethyl]benzamide
  参考文献：
  名称：

  New Benzocycloalkylpiperazines, Potent and Selective 5-HT_1A Receptor Ligands

  摘要：

  A series of 1-(benzocycloalkyl)-4-(benzamidoalkyl)piperazine derivatives was prepared in order to obtain compounds with a high affinity and selectivity for 5-HT1A receptors. The modifications of aromatic substituents, the length of the alkyl chain, and the size of the ring were explored. Most of N-(1,2,3,4-tetrahydronaphthyl)-N'-(benzamidoethyl)piperazines (32-37) were bound to 5-HT1A receptors in a nanomolar range and presented a high degree of selectivity. After resolution, levorotatory enantiomers showed affinity and selectivity higher than those of dextrorotatory ones for 5-HT1A sites. The agonist type activity of selected derivatives was also confirmed in vitro on the inhibition of the activation of adenylate cyclase induced by forskolin and, in vivo, on the induction of the lower lip retraction in rats.

  DOI：

  10.1021/jm950759z
• 作为产物：
  描述：

  6,7,8,9-四氢-5H-苯并环庚烯-5-醇 在 氢氧化钾 、 氯化亚砜 、 potassium carbonate 、 sodium iodide 作用下， 以 甲醇 、 甲苯 、 乙腈 为溶剂， 反应 49.0h， 生成 2-[2-[4-(6,7,8,9-tetrahydro-5H-benzo[7]annulen-5-yl)piperazin-1-yl]ethyl]isoindole-1,3-dione
  参考文献：
  名称：

  New Benzocycloalkylpiperazines, Potent and Selective 5-HT_1A Receptor Ligands

  摘要：

  A series of 1-(benzocycloalkyl)-4-(benzamidoalkyl)piperazine derivatives was prepared in order to obtain compounds with a high affinity and selectivity for 5-HT1A receptors. The modifications of aromatic substituents, the length of the alkyl chain, and the size of the ring were explored. Most of N-(1,2,3,4-tetrahydronaphthyl)-N'-(benzamidoethyl)piperazines (32-37) were bound to 5-HT1A receptors in a nanomolar range and presented a high degree of selectivity. After resolution, levorotatory enantiomers showed affinity and selectivity higher than those of dextrorotatory ones for 5-HT1A sites. The agonist type activity of selected derivatives was also confirmed in vitro on the inhibition of the activation of adenylate cyclase induced by forskolin and, in vivo, on the induction of the lower lip retraction in rats.

  DOI：

  10.1021/jm950759z