2-amino-6-(4-bromophenyl)-4-(1H-indol-3-yl)pyridine-3-carbonitrile | 224819-17-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 2-amino-6-(4-bromophenyl)-4-(1H-indol-3-yl)pyridine-3-carbonitrile
• CAS: 224819-17-4
• 化学式: C₂₀H₁₃BrN₄
• 分子量: 389.254
• InChiKey: WJJHKQGPPLYOFD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  25
• 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：
  78.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  异氰酸苯酯 、 2-amino-6-(4-bromophenyl)-4-(1H-indol-3-yl)pyridine-3-carbonitrile 在 montmorillonite K-10 作用下， 反应 0.08h， 以77%的产率得到
  参考文献：
  名称：

  取代吡啶和吡啶并[2,3-d]嘧啶衍生物的环保合成

  摘要：

  描述了一种从查耳酮和丙二腈中合成吡啶和吡啶并 [2,3-d] 嘧啶的环境友好的新型一锅法。在纯条件下使用微波辐射的反应中，观察到反应速率和产率的提高。

  DOI：

  10.1007/s11172-005-0440-z
• 作为产物：
  描述：

  4-溴苯乙酮 在 哌啶 、 ammonium acetate 作用下， 以 乙醇 为溶剂， 反应 48.0h， 生成 2-amino-6-(4-bromophenyl)-4-(1H-indol-3-yl)pyridine-3-carbonitrile
  参考文献：
  名称：

  Anti-inflammatory, analgesic and antipyretic 4,6-disubstituted 3-cyano-2-aminopyridines

  摘要：

  4,6-diaryl and 4,6-aryl-indolyl substituted 3-cyano-2-aminopyridines were synthesized and submitted to evaluation for their anti-inflammatory, analgesic and antipyretic activity. The electronegativity of the substituents and their displacement on the 4- or 6-aryl ring of the 4,6-diaryl-3-cyano-2-aminopyridine nucleus (3a-q) influenced the anti-inflammatory activity which was higher in the presence of electron-realising groups. The introduction of the indol-3-yl substituent in the 4-position of the 3-cyano-2-aminopyridine nucleus (6a-x) increased the anti-inflammatory and analgesic power, but there was no evidence of the relationship among the electronic characteristic of the substituents, their displacement on the 6-phenyl ring and the activity. Conversely, the displacement of the 2-hydroxyphenyl group in the 4-position (4a-e) and of the indol-3-yl group in the 6-position (8h-w) decreased the anti-inflammatory activity. All derivatives did not show any significative antipyretic activity. (C) Elsevier, Paris.

  DOI：

  10.1016/s0223-5234(99)80057-9

文献信息

• One-Pot Synthesis of 4,6-Diaryl-2-oxo(imino)-1,2-dihydropyridine-3-carbonitrile; a New Scaffold for p38α MAP Kinase Inhibition
  作者：Aya M. Serry、Sabine Luik、Stefan Laufer、Ashraf H. Abadi

  DOI：10.1021/cc1000488

  日期：2010.7.12

  multicomponent reaction of the appropriate acetophenone, aromatic aldehyde, ammonium acetate, and malononitrile or ethyl cyanoacetate. The products were obtained with excellent yields. The prepared compounds were evaluated for their in vitro ability to inhibit p38 alpha-MAP kinase. Several compounds showed p38 MAP kinase inhibitory properties with IC(50) as low as 0.07 microM. This is the first time to report

  通过适当的苯乙酮，芳香醛，铵的多组分反应，合成了两类通式为4,6-二芳基-2-氧代-1,2-二氢吡啶-3-腈的新化合物及其等规2-亚氨基衍生物。乙酸，丙二腈或氰基乙酸乙酯。获得的产物具有优异的产率。评价制备的化合物的体外抑制p38α-MAP激酶的能力。几种化合物显示p38 MAP激酶抑制特性，IC（50）低至0.07 microM。这是首次报道具有支架的化合物，例如p38α-MAP激酶抑制剂。这证明了在药物发现中多组分反应的潜力。