4-[(1-oxo-1H-phenalen-9-yl)amino]benzonitrile | 1225012-34-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 非那烯类
• 英文名称: 4-[(1-oxo-1H-phenalen-9-yl)amino]benzonitrile
• 英文别名: 4-[(9-Oxophenalen-1-yl)amino]benzonitrile；4-[(9-oxophenalen-1-yl)amino]benzonitrile
• CAS: 1225012-34-9
• 化学式: C₂₀H₁₂N₂O
• 分子量: 296.328
• InChiKey: SAJCIECOGPYDMD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  52.9
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-[(1-oxo-1H-phenalen-9-yl)amino]benzonitrile 在 三氟化硼乙醚 作用下， 以 邻二甲苯 为溶剂， 反应 14.0h， 以80%的产率得到2,2-difluoro-3-(4-cyanophenyl)-2-bora-s-3-aza-1-oxophenalene
  参考文献：
  名称：

  苯基硼氟配合物：合成、晶体结构和固态荧光特性

  摘要：

  已经合成了一系列新的苯基硼氟复合型荧光团，在溶液中具有强烈的荧光猝灭，但在固态时具有高荧光发射。X 射线结构表明，庞大的取代基导致空间位阻并阻止荧光团形成短的分子间相互作用，从而增强固态荧光发射。

  DOI：

  10.1016/j.molstruc.2010.01.027
• 作为产物：
  描述：

  9-羟基-萘嵌苯-1-酮 在 potassium phosphate 作用下， 以 四氢呋喃 、 水 、 甲苯 为溶剂， 反应 29.0h， 生成 4-[(1-oxo-1H-phenalen-9-yl)amino]benzonitrile
  参考文献：
  名称：

  Design, synthesis and evaluation of amino-substituted 1H-phenalen-1-ones as anti-leishmanial agents

  摘要：

  Screening of a designed collection of mono-substituted amino-IH-phenalen-1-ones against promastigote forms of L. donovani and L. amazonensis, identified seven compounds with anti-leishmanial activities comparable or better than the commonly prescribed anti-leishmanial drug, miltefosine. Structure activity analysis revealed that appendages containing a basic tertiary nitrogen were favored, and that the position of the appendage also affected their potency. Like miltefosine, several of these active compounds significantly reduced the mitochondrial membrane potential in promastigotes. Further studies in amastigotes of L. amazonensis revealed that compounds 14, 15 and 33 were more active and more selective than miltefosine, with sub-micromolar potencies and selectivity indices > 100. (C) 2017 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2017.10.032

文献信息

• Design, synthesis and evaluation of amino-substituted 1H-phenalen-1-ones as anti-leishmanial agents
  作者：Mónica Blanco Freijo、Atteneri López-Arencibia、José E. Piñero、Grant McNaughton-Smith、Teresa Abad-Grillo

  DOI：10.1016/j.ejmech.2017.10.032

  日期：2018.1

  Screening of a designed collection of mono-substituted amino-IH-phenalen-1-ones against promastigote forms of L. donovani and L. amazonensis, identified seven compounds with anti-leishmanial activities comparable or better than the commonly prescribed anti-leishmanial drug, miltefosine. Structure activity analysis revealed that appendages containing a basic tertiary nitrogen were favored, and that the position of the appendage also affected their potency. Like miltefosine, several of these active compounds significantly reduced the mitochondrial membrane potential in promastigotes. Further studies in amastigotes of L. amazonensis revealed that compounds 14, 15 and 33 were more active and more selective than miltefosine, with sub-micromolar potencies and selectivity indices > 100. (C) 2017 Elsevier Masson SAS. All rights reserved.
• Phenalenyl-based boron–fluorine complexes: Synthesis, crystal structures and solid-state fluorescence properties
  作者：Weibo Yan、Xiangjian Wan、Yongsheng Chen

  DOI：10.1016/j.molstruc.2010.01.027

  日期：2010.4

  boron–fluorine complex-type fluorophores, with a drastic fluorescence quenching in solution but high fluorescence emission in the solid-state, have been synthesized. The X-ray structure demonstrates that the bulky substituents result in steric hindrance and prevent the fluorophores forming short intermolecular interaction thereby enhancing the solid-state fluorescence emission.

  已经合成了一系列新的苯基硼氟复合型荧光团，在溶液中具有强烈的荧光猝灭，但在固态时具有高荧光发射。X 射线结构表明，庞大的取代基导致空间位阻并阻止荧光团形成短的分子间相互作用，从而增强固态荧光发射。