2-(4-fluorophenyl)-1H-indole-6-carbonitrile | 1207731-23-4

• 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: 2-(4-fluorophenyl)-1H-indole-6-carbonitrile
• CAS: 1207731-23-4
• 化学式: C₁₅H₉FN₂
• 分子量: 236.248
• InChiKey: YZVYPOBHAIYKJV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  39.6
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(4-fluorophenyl)-1H-indole-6-carbonitrile 在 硫酸 、 三氟乙酸 、 水 作用下， 以 正己烷 、 二氯甲烷 为溶剂， 反应 24.0h， 生成 2-(4-fluorophenyl)-1H-indole-6-carboxamide
  参考文献：
  名称：

  Synthesis and Biological Evaluation of Botulinum Neurotoxin A Protease Inhibitors

  摘要：

  NSC 240898 was previously identified as a botulinum neurotoxin A light chain (BoNT/A LC) endopeptidase inhibitor by screening the National Cancer Institute Open Repository diversity set. Two types of analogues have been synthesized and shown to inhibit BoNT/A LC in a FRET-based enzyme assay, with confirmation in an HPLC-based assay. These two series of compounds have also been evaluated for inhibition of anthrax lethal factor (LF), an unrelated metalloprotease, to examine enzyme specificity of the BoNT/A LC inhibition. The most potent inhibitor against BoNT/A LC in these two series is compound 12 (IC50 = 2.5 mu M, FRET assay), which is 4.4-fold more potent than the lead structure and 11.2-fold more selective for BoNT/A LC versus the anthrax LF metalloproteinase. Structure-activity relationship studies have revealed structural features important to potency and enzyme specificity.

  DOI：

  10.1021/jm901852f
• 作为产物：
  描述：

  (E)-1-(4-fluorophenyl)-2-(4-cyano-2-nitrophenyl)ethene 以 亚磷酸三乙酯 为溶剂， 反应 1.5h， 以45%的产率得到2-(4-fluorophenyl)-1H-indole-6-carbonitrile
  参考文献：
  名称：

  Synthesis and Biological Evaluation of Botulinum Neurotoxin A Protease Inhibitors

  摘要：

  NSC 240898 was previously identified as a botulinum neurotoxin A light chain (BoNT/A LC) endopeptidase inhibitor by screening the National Cancer Institute Open Repository diversity set. Two types of analogues have been synthesized and shown to inhibit BoNT/A LC in a FRET-based enzyme assay, with confirmation in an HPLC-based assay. These two series of compounds have also been evaluated for inhibition of anthrax lethal factor (LF), an unrelated metalloprotease, to examine enzyme specificity of the BoNT/A LC inhibition. The most potent inhibitor against BoNT/A LC in these two series is compound 12 (IC50 = 2.5 mu M, FRET assay), which is 4.4-fold more potent than the lead structure and 11.2-fold more selective for BoNT/A LC versus the anthrax LF metalloproteinase. Structure-activity relationship studies have revealed structural features important to potency and enzyme specificity.

  DOI：

  10.1021/jm901852f

文献信息

• Studies on the mechanism of the Cadogan–Sundberg indole synthesis
  作者：Helena Majgier-Baranowska、John D. Williams、Bing Li、Norton P. Peet

  DOI：10.1016/j.tetlet.2012.06.146

  日期：2012.8

  The Cadogan-Sundberg indole synthesis produces two major products from the treatment of 2-nitrostilbenes with triethyl phosphite, which are the 2-arylindoles and the corresponding 2-aryl-N-ethoxyindoles. We were interested in determining the origin of the oxygen atom in the 2-aryl-N-ethoxyindoles. In this study, we verify that this oxygen atom originates from the nitro group and not from the triethyl phosphite. (c) 2012 Published by Elsevier Ltd.