2-(3-spiro[isobenzofuran-1(3H),4'-piperidine-1-yl]propyl)-1H-indole-1,3(2H)-dione | 475152-12-6

• 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-(3-spiro[isobenzofuran-1(3H),4'-piperidine-1-yl]propyl)-1H-indole-1,3(2H)-dione
• 英文别名: 2-(3-spiro[1H-2-benzofuran-3,4'-piperidine]-1'-ylpropyl)isoindole-1,3-dione
• CAS: 475152-12-6
• 化学式: C₂₃H₂₄N₂O₃
• 分子量: 376.455
• InChiKey: ITKSTFHNIUDTKJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  49.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(3-spiro[isobenzofuran-1(3H),4'-piperidine-1-yl]propyl)-1H-indole-1,3(2H)-dione 在 一水合肼 作用下， 以 乙醇 为溶剂， 反应 3.0h， 以99%的产率得到3-spiro[isobenzofuran-1(3H),4'-piperidine]-1-ylpropane-1-amine
  参考文献：
  名称：

  Discovery of novel spiro-piperidine derivatives as highly potent and selective melanin-concentrating hormone 1 receptor antagonists

  摘要：

  Optimization of high-throughput screening hit 1a led to the identification of a novel spiro-piperidine class of melanin-concentrating hormone 1 receptor (MCH-1R) antagonists. Compound 3c was identified as a highly potent and selective MCH-1R antagonist, which has an IC50 value of 0.09 nM at hMCH-1R. The synthesis and structure-activity relationships of the novel spiro-piperidine MCH-1R antagonists are described. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.04.016
• 作为产物：
  描述：

  3H-螺[2-苯并呋喃-1,4'-哌啶] 、 N-(3-溴丙基)苯二胺 在 potassium carbonate 、 potassium iodide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 17.0h， 生成 2-(3-spiro[isobenzofuran-1(3H),4'-piperidine-1-yl]propyl)-1H-indole-1,3(2H)-dione
  参考文献：
  名称：

  Discovery of novel spiro-piperidine derivatives as highly potent and selective melanin-concentrating hormone 1 receptor antagonists

  摘要：

  Optimization of high-throughput screening hit 1a led to the identification of a novel spiro-piperidine class of melanin-concentrating hormone 1 receptor (MCH-1R) antagonists. Compound 3c was identified as a highly potent and selective MCH-1R antagonist, which has an IC50 value of 0.09 nM at hMCH-1R. The synthesis and structure-activity relationships of the novel spiro-piperidine MCH-1R antagonists are described. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.04.016

文献信息

• Identification of a Novel Spiropiperidine Opioid Receptor-like 1 Antagonist Class by a Focused Library Approach Featuring 3D-Pharmacophore Similarity
  作者：Yasuhiro Goto、Sachie Arai-Otsuki、Yukari Tachibana、Daisuke Ichikawa、Satoshi Ozaki、Hiroyuki Takahashi、Yoshikazu Iwasawa、Osamu Okamoto、Shoki Okuda、Hisashi Ohta、Takeshi Sagara

  DOI：10.1021/jm0509851

  日期：2006.2.1

  A focused library approach identifying novel leads to develop a potent ORL1 antagonist is described. Beginning from a compound identified by random screening, an exploratory library that exhibited a diverse display of pharmacophores was designed. After evaluating ORL1 antagonistic activity, a highly focused library was designed based on 3D-pharmacophore similarity to known actives. A novel D-proline amide class was identified in this library and was found to possess potent ORL1 antagonistic activity.