benzyl 4-[1-(toluene-4-sulfonyl)-1H-indol-4-yl]-piperazine-1-carboxylate | 1258408-23-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: benzyl 4-[1-(toluene-4-sulfonyl)-1H-indol-4-yl]-piperazine-1-carboxylate
• 英文别名: benzyl 4-[1-(toluene-4-sulfonyl)-1H-indol-4-yl]piperazine-1-carboxylate
• CAS: 1258408-23-9
• 化学式: C₂₇H₂₇N₃O₄S
• 分子量: 489.595
• InChiKey: NYXCDQLPNQNIGW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.65
• 重原子数：
  35.0
• 可旋转键数：
  5.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  71.85
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  benzyl 4-[1-(toluene-4-sulfonyl)-1H-indol-4-yl]-piperazine-1-carboxylate 在 苄基三乙基氯化铵 、 magnesium 、 对甲苯磺酰肼 、 sodium hydroxide 、 三氯氧磷 作用下， 以 四氢呋喃 、 甲醇 、 水 、 甲苯 为溶剂， 反应 8.95h， 生成 benzyl 4-(toluene-4-sulfonyl)-4,6,6a,7,9,10-hexahydro-4,8,10a-triaza-acephenanthrylene-8-carboxylate
  参考文献：
  名称：

  Novel Aza-analogous Ergoline Derived Scaffolds as Potent Serotonin 5-HT₆ and Dopamine D₂ Receptor Ligands.

  摘要：

  By introducing distal substituents on a tetracyclic scaffold resembling the ergoline structure, two series of analogues were achieved exhibiting subnanomolar receptor binding affinities for the dopamine D-2 and serotonin S-HT6 receptor subtype, respectively. While the S-HT6 ligands were antagonists, the D-2 ligands displayed intrinsic activities ranging from full agonism to partial agonism with low intrinsic activity. These structures could potentially be interesting for treatment of neurological diseases such as schizophrenia, Parkinson's disease, and cognitive deficits.

  DOI：

  10.1021/jm5003759
• 作为产物：
  描述：

  4-溴吲哚 、 对甲苯磺酰氯 在 四丁基硫酸氢铵 、 sodium hydroxide 、 bis(dibenzylideneacetone)-palladium⁽⁰⁾ 、 2-(二叔丁基膦)联苯 、 sodium t-butanolate 作用下， 以 水 、 甲苯 为溶剂， 反应 20.67h， 生成 benzyl 4-[1-(toluene-4-sulfonyl)-1H-indol-4-yl]-piperazine-1-carboxylate
  参考文献：
  名称：

  Novel Aza-analogous Ergoline Derived Scaffolds as Potent Serotonin 5-HT₆ and Dopamine D₂ Receptor Ligands.

  摘要：

  By introducing distal substituents on a tetracyclic scaffold resembling the ergoline structure, two series of analogues were achieved exhibiting subnanomolar receptor binding affinities for the dopamine D-2 and serotonin S-HT6 receptor subtype, respectively. While the S-HT6 ligands were antagonists, the D-2 ligands displayed intrinsic activities ranging from full agonism to partial agonism with low intrinsic activity. These structures could potentially be interesting for treatment of neurological diseases such as schizophrenia, Parkinson's disease, and cognitive deficits.

  DOI：

  10.1021/jm5003759

文献信息

• Syntheses of aza-analogous iso-ergoline scaffolds using carbene mediated C–H insertion
  作者：Niels Krogsgaard-Larsen、Mikael Begtrup、Karla Frydenvang、Jan Kehler

  DOI：10.1016/j.tet.2010.09.023

  日期：2010.11

  A novel direct flexible and robust approach to the iso-ergoline tetracyclic system in which a five or six-membered ring is established by intramolecular carbene C-H insertion is reported The protocol involves a two step conversion of an aromatic aldehyde to the corresponding hydrazone and without purification further conversion to the diazo-compound followed by thermal carbene formation and C-H insertion alpha to a nitrogen (C) 2010 Elsevier Ltd All rights reserved