4-氟-N-(4-氟-2-甲基苯基)苯甲酰胺 | 876918-15-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 4-氟-N-(4-氟-2-甲基苯基)苯甲酰胺
• 英文名称: 4-fluoro-N-(4-fluoro-2-methylphenyl)benzamide
• CAS: 876918-15-9
• 化学式: C₁₄H₁₁F₂NO
• mdl: MFCD07264151
• 分子量: 247.244
• InChiKey: JCAMDFOHYNPDOV-UHFFFAOYSA-N

物化性质

• 熔点：
  172-175 °C(Solv: toluene (108-88-3))
• 沸点：
  271.1±40.0 °C(Predicted)
• 密度：
  1.281±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.071
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-氟-N-(4-氟-2-甲基苯基)苯甲酰胺 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 以30%的产率得到5-fluoro-2-(4-fluorophenyl)indole
  参考文献：
  名称：

  Anxiolytic-like Effects of N,N-Dialkyl-2-phenylindol-3-ylglyoxylamides by Modulation of Translocator Protein Promoting Neurosteroid Biosynthesis

  摘要：

  Novel N,N-disubstituted indol-3-ylglyoxylamides (1-56), bearing different combinations of substituents R-1-R-5, were synthesized and evaluated as ligands of the translocator protein (TSPO), the 18 kDa protein representing the minimal functional unit of the "peripheral-type benzodiazepine receptor" (PBR). Most of the new compounds showed a nanomolar/subnanomolar affinity for TSPO and stimulated steroid biosynthesis in rat C6 glioma cells with a potency similar to or higher than that of classic TSPO ligands such as PK 11195. Moreover, when evaluated in vivo by means of the elevated-plus-maze (EPM) paradigm in the rat, compound 32. the best-performing derivative in terms of TSPO affinity and pregnenolone production, showed clear anxiolytic effects. The results of this study suggested that the novel N, N-di substituted indol-3y1glyoxylani ides may represent a promising class of compounds potentially suited for the treatment of anxiety disorders.

  DOI：

  10.1021/jm8003224
• 作为产物：
  描述：

  4-氟-2-甲基苯胺 、 对氟苯甲酰氯 在 三乙胺 作用下， 以 甲苯 为溶剂， 以72%的产率得到4-氟-N-(4-氟-2-甲基苯基)苯甲酰胺
  参考文献：
  名称：

  Anxiolytic-like Effects of N,N-Dialkyl-2-phenylindol-3-ylglyoxylamides by Modulation of Translocator Protein Promoting Neurosteroid Biosynthesis

  摘要：

  Novel N,N-disubstituted indol-3-ylglyoxylamides (1-56), bearing different combinations of substituents R-1-R-5, were synthesized and evaluated as ligands of the translocator protein (TSPO), the 18 kDa protein representing the minimal functional unit of the "peripheral-type benzodiazepine receptor" (PBR). Most of the new compounds showed a nanomolar/subnanomolar affinity for TSPO and stimulated steroid biosynthesis in rat C6 glioma cells with a potency similar to or higher than that of classic TSPO ligands such as PK 11195. Moreover, when evaluated in vivo by means of the elevated-plus-maze (EPM) paradigm in the rat, compound 32. the best-performing derivative in terms of TSPO affinity and pregnenolone production, showed clear anxiolytic effects. The results of this study suggested that the novel N, N-di substituted indol-3y1glyoxylani ides may represent a promising class of compounds potentially suited for the treatment of anxiety disorders.

  DOI：

  10.1021/jm8003224

文献信息

• Anxiolytic-like Effects of <i>N</i>,<i>N</i>-Dialkyl-2-phenylindol-3-ylglyoxylamides by Modulation of Translocator Protein Promoting Neurosteroid Biosynthesis
  作者：Federico Da Settimo、Francesca Simorini、Sabrina Taliani、Concettina La Motta、Anna Maria Marini、Silvia Salerno、Marusca Bellandi、Ettore Novellino、Giovanni Greco、Barbara Cosimelli、Eleonora Da Pozzo、Barbara Costa、Nicola Simola、Micaela Morelli、Claudia Martini

  DOI：10.1021/jm8003224

  日期：2008.9.25

  Novel N,N-disubstituted indol-3-ylglyoxylamides (1-56), bearing different combinations of substituents R-1-R-5, were synthesized and evaluated as ligands of the translocator protein (TSPO), the 18 kDa protein representing the minimal functional unit of the "peripheral-type benzodiazepine receptor" (PBR). Most of the new compounds showed a nanomolar/subnanomolar affinity for TSPO and stimulated steroid biosynthesis in rat C6 glioma cells with a potency similar to or higher than that of classic TSPO ligands such as PK 11195. Moreover, when evaluated in vivo by means of the elevated-plus-maze (EPM) paradigm in the rat, compound 32. the best-performing derivative in terms of TSPO affinity and pregnenolone production, showed clear anxiolytic effects. The results of this study suggested that the novel N, N-di substituted indol-3y1glyoxylani ides may represent a promising class of compounds potentially suited for the treatment of anxiety disorders.