5-(2-fluoroethoxy)indole | 1240407-43-5

• 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: 5-(2-fluoroethoxy)indole
• 英文别名: 5-(2-fluoroethoxy)-1H-indole
• CAS: 1240407-43-5
• 化学式: C₁₀H₁₀FNO
• mdl: MFCD20687945
• 分子量: 179.194
• InChiKey: VRTAUTLAOMSHHQ-UHFFFAOYSA-N

物化性质

• 沸点：
  331.9±22.0 °C(Predicted)
• 密度：
  1.212±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  25
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-(2-fluoroethoxy)indole 在 四丁基氟化铵 、 potassium carbonate 、 potassium hydroxide 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 8.0h， 生成 1-[4-(5,6-dimethoxyisoindolin-2-yl)butyl]-5-(2-fluoroethoxy)indole
  参考文献：
  名称：

  18 F-Labeled indole-based analogs as highly selective radioligands for imaging sigma-2 receptors in the brain

  摘要：

  We have designed and synthesized a series of indole-based sigma(2) receptor ligands containing 5,6-dimethoxyisoindoline or 6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline as pharmacophore. In vitro competition binding assays showed that all ten ligands possessed low nanomolar affinity (K-i=1.79-5.23 nM) for sigma(2) receptors and high subtype selectivity (K-1(sigma(2))/K-1 (sigma(1)) = 56-708). Moreover, they showed high selectivity for sigma(2) receptor over the vesicular acetylcholine transporter (>1000-fold). The corresponding radiotracers [F-18]16 and [F-18]21 were prepared by an efficient one-pot, two-step reaction sequence with a home-made automated synthesis module, with 10-15% radiochemical yield and radiochemical purity of >99%. Both radiotracers showed high brain uptake and o-2 receptor binding specificity in mice. (C) 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2017.05.019
• 作为产物：
  描述：

  5-羟基吲哚 、 1-溴-2-氟乙烷 在 potassium carbonate 作用下， 以 乙腈 为溶剂， 反应 6.0h， 以69%的产率得到5-(2-fluoroethoxy)indole
  参考文献：
  名称：

  18 F-Labeled indole-based analogs as highly selective radioligands for imaging sigma-2 receptors in the brain

  摘要：

  We have designed and synthesized a series of indole-based sigma(2) receptor ligands containing 5,6-dimethoxyisoindoline or 6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline as pharmacophore. In vitro competition binding assays showed that all ten ligands possessed low nanomolar affinity (K-i=1.79-5.23 nM) for sigma(2) receptors and high subtype selectivity (K-1(sigma(2))/K-1 (sigma(1)) = 56-708). Moreover, they showed high selectivity for sigma(2) receptor over the vesicular acetylcholine transporter (>1000-fold). The corresponding radiotracers [F-18]16 and [F-18]21 were prepared by an efficient one-pot, two-step reaction sequence with a home-made automated synthesis module, with 10-15% radiochemical yield and radiochemical purity of >99%. Both radiotracers showed high brain uptake and o-2 receptor binding specificity in mice. (C) 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2017.05.019

文献信息

• Synthesis and characterization of selective dopamine D2 receptor antagonists. 2. Azaindole, benzofuran, and benzothiophene analogs of L-741,626
  作者：Suwanna Vangveravong、Michelle Taylor、Jinbin Xu、Jinquan Cui、Wesley Calvin、Sonja Babic、Robert R. Luedtke、Robert H. Mach

  DOI：10.1016/j.bmc.2010.05.052

  日期：2010.7

  A series of indole, 7-azaindole, benzofuran, and benzothiophene compounds have been prepared and evaluated for affinity at D2-like dopamine receptors. These compounds share structural elements with the classical D2-like dopamine receptor antagonists haloperidol, N-methylspiperone and benperidol. Two new compounds, 4-(4-iodophenyl)-1-((4-methoxy-1H-indol-3-yl) methyl) piperidin-4-ol (6) and 4-(4-iodophenyl)-1-((5-methoxy-1H-indol-3-yl) methyl) piperidin-4-ol (7), were found to have high affinity to and selectivity for D2 versus D3 receptors. Changing the aromatic ring system from an indole to other heteroaromatic ring systems reduced the D2 binding affinity and the D2 versus D3 selectivity. (C) 2010 Elsevier Ltd. All rights reserved.
• 18 F-Labeled indole-based analogs as highly selective radioligands for imaging sigma-2 receptors in the brain
  作者：Liang Wang、Jiajun Ye、Yingfang He、Winnie Deuther-Conrad、Jinming Zhang、Xiaojun Zhang、Mengchao Cui、Jörg Steinbach、Yiyun Huang、Peter Brust、Hongmei Jia

  DOI：10.1016/j.bmc.2017.05.019

  日期：2017.7

  We have designed and synthesized a series of indole-based sigma(2) receptor ligands containing 5,6-dimethoxyisoindoline or 6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline as pharmacophore. In vitro competition binding assays showed that all ten ligands possessed low nanomolar affinity (K-i=1.79-5.23 nM) for sigma(2) receptors and high subtype selectivity (K-1(sigma(2))/K-1 (sigma(1)) = 56-708). Moreover, they showed high selectivity for sigma(2) receptor over the vesicular acetylcholine transporter (>1000-fold). The corresponding radiotracers [F-18]16 and [F-18]21 were prepared by an efficient one-pot, two-step reaction sequence with a home-made automated synthesis module, with 10-15% radiochemical yield and radiochemical purity of >99%. Both radiotracers showed high brain uptake and o-2 receptor binding specificity in mice. (C) 2017 Elsevier Ltd. All rights reserved.