Benzonitrile,4-(1h-indol-5-ylcarbonyl)- | 881006-20-8

• 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: Benzonitrile,4-(1h-indol-5-ylcarbonyl)-
• 英文别名: 4-(1H-indole-5-carbonyl)benzonitrile
• CAS: 881006-20-8
• 化学式: C₁₆H₁₀N₂O
• 分子量: 246.268
• InChiKey: UWRVZCQRYUWAKJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  56.6
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  Benzonitrile,4-(1h-indol-5-ylcarbonyl)- 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 生成 4-[Hydroxy-(1H-indol-5-yl)-methyl]-benzonitrile
  参考文献：
  名称：

  Synthesis and biological evaluation of 5-[(aryl)(1H-imidazol-1-yl)methyl]-1H-indoles: Potent and selective aromatase inhibitors

  摘要：

  The synthesis and the aromatase (CYP19) inhibitory activity of 5-[(aryl)(imidazol-1-yl)methyl]-1H-indoles were reported. Among the tested racemate compounds, 5-[(4-chlorophenyl)(1H-imidazol-1-yl)methyl]-1H-indole 8b emerged as a potent CYP19 inhibitor (IC50 = 15.3 nM). Chiral chromatography allowed isolation of the (+) enantiomer 8b2, which was about twice as active as the racemate (IC50 = 9 nM). (C) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.11.099
• 作为产物：
  描述：

  (4-Bromo-phenyl)-(2,3-dihydro-1H-indol-5-yl)-methanone 在 manganese(IV) oxide 、 四(三苯基膦)钯 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 16.07h， 生成 Benzonitrile,4-(1h-indol-5-ylcarbonyl)-
  参考文献：
  名称：

  Synthesis and biological evaluation of 5-[(aryl)(1H-imidazol-1-yl)methyl]-1H-indoles: Potent and selective aromatase inhibitors

  摘要：

  The synthesis and the aromatase (CYP19) inhibitory activity of 5-[(aryl)(imidazol-1-yl)methyl]-1H-indoles were reported. Among the tested racemate compounds, 5-[(4-chlorophenyl)(1H-imidazol-1-yl)methyl]-1H-indole 8b emerged as a potent CYP19 inhibitor (IC50 = 15.3 nM). Chiral chromatography allowed isolation of the (+) enantiomer 8b2, which was about twice as active as the racemate (IC50 = 9 nM). (C) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.11.099

文献信息

• Efficient synthesis of 5- and 6-tributylstannylindoles and their reactivity with acid chlorides in the Stille coupling reaction
  作者：Khalil Cherry、Nicolas Lebegue、Veronique Leclerc、Pascal Carato、Saïd Yous、Pascal Berthelot

  DOI：10.1016/j.tetlet.2007.06.084

  日期：2007.8

  Several 5- and 6-acylindoles have been synthesized in good yield by means of palladium catalyzed cross-coupling reactions between acid chloride derivatives and 5- or 6-tributylstannylindoles to give useful intermediates for the synthesis of analogues of biologically and pharmacologically active molecules.

  借助于酰基氯衍生物与5-或6-三丁基锡三羟甲基吲哚之间的钯催化的交叉偶联反应，已经以良好的产率合成了几种5-和6-酰基环吲哚，以提供有用的中间体，用于合成生物和药理活性分子的类似物。
• Synthesis and biological evaluation of 5-[(aryl)(1H-imidazol-1-yl)methyl]-1H-indoles: Potent and selective aromatase inhibitors
  作者：Marie-Pierre Lézé、Marc Le Borgne、Patricia Pinson、Anja Palusczak、Muriel Duflos、Guillaume Le Baut、Rolf W. Hartmann

  DOI：10.1016/j.bmcl.2005.11.099

  日期：2006.3

  The synthesis and the aromatase (CYP19) inhibitory activity of 5-[(aryl)(imidazol-1-yl)methyl]-1H-indoles were reported. Among the tested racemate compounds, 5-[(4-chlorophenyl)(1H-imidazol-1-yl)methyl]-1H-indole 8b emerged as a potent CYP19 inhibitor (IC50 = 15.3 nM). Chiral chromatography allowed isolation of the (+) enantiomer 8b2, which was about twice as active as the racemate (IC50 = 9 nM). (C) 2005 Elsevier Ltd. All rights reserved.