3-(4-bromobutyl)-5-fluoro-1H-indole | 793671-26-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 3-(4-bromobutyl)-5-fluoro-1H-indole
• CAS: 793671-26-8
• 化学式: C₁₂H₁₃BrFN
• 分子量: 270.144
• InChiKey: ZATIJBYYCZSMOL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  15.8
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3-(4-bromobutyl)-5-fluoro-1H-indole 、 N-cyclohexyl-N-phenyl-2-(piperazin-1-yl)acetamide 在 potassium carbonate 作用下， 以 乙腈 为溶剂， 反应 12.0h， 以29.5%的产率得到N-cyclohexyl-2-(4-(4-(5-fluoro-1H-indol-3-yl)butyl)piperazin-1-yl)-N-phenylacetamide
  参考文献：
  名称：

  Design, Synthesis, and Evaluation of Indolebutylamines as a Novel Class of Selective Dopamine D3 Receptor Ligands

  摘要：

  A series of indolebutylamine derivatives were designed, synthesized, and evaluated as a novel class of selective ligands for the dopamine 3 receptor. The most potent compound 11q binds to dopamine 3 receptor with a Ki value of 124 nm and displays excellent selectivity over the dopamine 1 receptor and dopamine 2 receptor. Investigation based on structural information indicates that site S182 located in extracellular loop 2 may account for high selectivity of compounds. Interaction models of the dopamine 3 receptor‐11q complex and structure‐activity relationships were discussed by integrating all available experimental and computational data with the eventual aim to discover potent and selective ligands to dopamine 3 receptor.

  DOI：

  10.1111/cbdd.12158
• 作为产物：
  描述：

  3-(5-氟-1H-3-吲哚)-1-丙醇 在 四溴化碳 、 四丁基氟化铵 、 三苯基膦 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 3-(4-bromobutyl)-5-fluoro-1H-indole
  参考文献：
  名称：

  Design, Synthesis, and Evaluation of Indolebutylamines as a Novel Class of Selective Dopamine D3 Receptor Ligands

  摘要：

  A series of indolebutylamine derivatives were designed, synthesized, and evaluated as a novel class of selective ligands for the dopamine 3 receptor. The most potent compound 11q binds to dopamine 3 receptor with a Ki value of 124 nm and displays excellent selectivity over the dopamine 1 receptor and dopamine 2 receptor. Investigation based on structural information indicates that site S182 located in extracellular loop 2 may account for high selectivity of compounds. Interaction models of the dopamine 3 receptor‐11q complex and structure‐activity relationships were discussed by integrating all available experimental and computational data with the eventual aim to discover potent and selective ligands to dopamine 3 receptor.

  DOI：

  10.1111/cbdd.12158

文献信息

• [EN] QUINOLINE 3-AMINO CHROMAN DERIVATIVES<br/>[FR] AMINO-PYRANOQUINOLEINES EN TANT QU'INHIBITEURS DE RECAPTAGE DE LA SEROTONINE ET AGONISTES DE RECEPTEURS 5-HT1A
  申请人：WYETH CORP

  公开号：WO2004099214A1

  公开（公告）日：2004-11-18

  Quinoline 3 -amino chroman derivatives and compositions containing such compounds are disclosed. Methods for using the quinoline 3-amino chroman derivatives and compositions containing such compounds in the treatment of serotonin disorders are disclosed. Also disclosed are processes for preparing quinoline 3-amino chroman derivatives.

  揭示了喹啉3-氨基色苷衍生物和含有这种化合物的组合物。还揭示了使用喹啉3-氨基色苷衍生物和含有这种化合物的组合物来治疗血清素紊乱的方法。还揭示了制备喹啉3-氨基色苷衍生物的方法。
• Quinoline 3-amino chroman derivatives
  申请人：Hatzenbuhler Theriault Nicole

  公开号：US20050004157A1

  公开（公告）日：2005-01-06

  Quinoline 3-amino chroman derivatives and compositions containing such compounds are disclosed. Methods for using the quinoline 3-amino chroman derivatives and compositions containing such compounds in the treatment of serotonin disorders are disclosed. Also disclosed are processes for preparing quinoline 3-amino chroman derivatives.

  本发明公开了喹啉3-氨基色基衍生物和含有这种化合物的组合物。公开了使用喹啉3-氨基色基衍生物和含有这种化合物的组合物治疗血清素失调的方法。还公开了制备喹啉3-氨基色基衍生物的方法。
• QUINOLINE 3-AMINO CHROMAN DERIVATIVES
  申请人：Hatzenbuhler Theriault Nicole

  公开号：US20070191417A1

  公开（公告）日：2007-08-16

  Quinoline 3-amino chroman derivatives and compositions containing such compounds are disclosed. Methods for using the quinoline 3-amino chroman derivatives and compositions containing such compounds in the treatment of serotonin disorders are disclosed. Also disclosed are processes for preparing quinoline 3-amino chroman derivatives.

  本文揭示了喹啉3-氨基色基衍生物和含有这种化合物的组合物。还揭示了利用喹啉3-氨基色基衍生物和含有这种化合物的组合物治疗血清素失调的方法。同时，还揭示了制备喹啉3-氨基色基衍生物的过程。
• US7227023B2
  申请人：——

  公开号：US7227023B2

  公开（公告）日：2007-06-05
• Design, Synthesis, and Evaluation of Indolebutylamines as a Novel Class of Selective Dopamine D3 Receptor Ligands
  作者：Peng Du、Lili Xu、Jiye Huang、Kunqian Yu、Rui Zhao、Bo Gao、Hualiang Jiang、Weili Zhao、Xuechu Zhen、Wei Fu

  DOI：10.1111/cbdd.12158

  日期：2013.9

  A series of indolebutylamine derivatives were designed, synthesized, and evaluated as a novel class of selective ligands for the dopamine 3 receptor. The most potent compound 11q binds to dopamine 3 receptor with a Ki value of 124 nm and displays excellent selectivity over the dopamine 1 receptor and dopamine 2 receptor. Investigation based on structural information indicates that site S182 located in extracellular loop 2 may account for high selectivity of compounds. Interaction models of the dopamine 3 receptor‐11q complex and structure‐activity relationships were discussed by integrating all available experimental and computational data with the eventual aim to discover potent and selective ligands to dopamine 3 receptor.