1-(5-溴-1H-吲哚-3-基)-2-(哌啶-1-基)乙烷-1,2-二酮 | 199658-92-9

• 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
• 中文名称: 1-(5-溴-1H-吲哚-3-基)-2-(哌啶-1-基)乙烷-1,2-二酮
• 中文别名: 1-(5-溴-1H-吲哚-3-基)-2-(吡咯烷-1-基)-1,2-乙二酮
• 英文名称: 1-(5-bromo-1H-indol-3-yl)-2-pyrrolidin-1-yl-ethane-1,2-dione
• 英文别名: 5-bromo-3-(1-pyrrolidinylglyoxyl)-1H-indole；1-(5-Bromo-1H-indol-3-YL)-2-(pyrrolidin-1-YL)ethane-1,2-dione；1-(5-bromo-1H-indol-3-yl)-2-pyrrolidin-1-ylethane-1,2-dione
• CAS: 199658-92-9
• 化学式: C₁₄H₁₃BrN₂O₂
• 分子量: 321.173
• InChiKey: WDCRWMFQABHAKT-UHFFFAOYSA-N

物化性质

• 熔点：
  212 °C(Solv: methanol (67-56-1))
• 沸点：
  497.4±48.0 °C(Predicted)
• 密度：
  1.613±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  53.2
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  1-(5-溴-1H-吲哚-3-基)-2-(哌啶-1-基)乙烷-1,2-二酮 在 lithium aluminium tetrahydride 、 叔丁基锂 、 sodium hexamethyldisilazane 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 正戊烷 为溶剂， 反应 24.0h， 生成 3-(2-Pyrrolidin-1-yl-ethyl)-5-(1,2,3,6-tetrahydro-pyridin-4-yl)-1H-indole
  参考文献：
  名称：

  3-(2-Pyrrolidin-1-ylethyl)-5-(1,2,3,6-tetrahydropyridin-4-yl)-1H-indole derivatives as high affinity human 5-HT1B/1D ligands

  摘要：

  A series of 3-(2-pyrrolidin-1-ylethyl)-5-(1,2,3,6-tetrahydropyridin-4-yl)-1H-indole derivatives (2) has been prepared using parallel synthesis techniques, and their structure-activity relationships studied. High affinity human 5-HT1B/1D (h5-HT1B/1D) ligands have been identified. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2003.11.023
• 作为产物：
  描述：

  5-溴吲哚 以 乙醚 、 二氯甲烷 为溶剂， 反应 2.0h， 生成 1-(5-溴-1H-吲哚-3-基)-2-(哌啶-1-基)乙烷-1,2-二酮
  参考文献：
  名称：

  5-CYCLO INDOLE COMPOUNDS AS 5-HT1D RECEPTOR LIGANDS

  摘要：

  公开号：

  EP0944595B1

文献信息

• 5-Thienyltryptamine derivatives as serotonin 5-HT 1B/1D receptor agonists: potential treatments for migraine
  作者：Charles Q. Meng、Suman Rakhit、David K.H. Lee、Rajender Kamboj、Kirk L. McCallum、Lucy Mazzocco、Kerry Dyne、Abdelmalik Slassi

  DOI：10.1016/s0960-894x(00)00133-5

  日期：2000.5

  A series of 5-(2- or 3-thienyl)tryptamine derivatives (9) has been synthesized and shown to be potent and selective 5-HT1D versus 5-HT1B receptor agonists and, therefore, potential treatments for migraine. (C) 2000 Elsevier Science Ltd. All rights reserved.
• Synthesis and evaluation of indole-based new scaffolds for antimicrobial activities—Identification of promising candidates
  作者：Palwinder Singh、Puja Verma、Bhawna Yadav、Sneha S. Komath

  DOI：10.1016/j.bmcl.2011.04.001

  日期：2011.6

  Search for new antimicrobial agents led to the synthesis of series of N-1, C-3 and C-5 substituted bis-indoles. Their evaluation for antifungal and antibacterial activities resulted in the optimization of pyrrolidine/morpholine/N-benzyl moiety at the C-3 end and propane/butane/xylidine groups as linkers between two indoles for significant inhibition of microbial growth. Preliminary investigations have identified three highly potent antimicrobial agents. Dockings of these molecules in the active sites of lanosterol demethylase, dihydrofolate reductase and topoisomerase II indicate their strong interactions with these enzymes. (C) 2011 Elsevier Ltd. All rights reserved.