N,2,2,2-triphenyl-N-(pyridin-4-yl)acetamide

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: N,2,2,2-triphenyl-N-(pyridin-4-yl)acetamide
• 英文别名: 2,2,2-triphenyl-N-(pyridin-4-yl)acetamide；2,2,2-triphenyl-N-pyridin-4-yl-acetamide；2,2,2-triphenyl-N-pyridin-4-ylacetamide
• 化学式: C₂₅H₂₀N₂O
• 分子量: 364.447
• InChiKey: ZVTMFFIMAVIPIR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  42
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  三苯基乙酸 在 正丁基锂 、 potassium carbonate 作用下， 以 四氢呋喃 、 正己烷 、 丙酮 为溶剂， 反应 1.0h， 生成 N,2,2,2-triphenyl-N-(pyridin-4-yl)acetamide
  参考文献：
  名称：

  烯丙基酯与双锂芳基酰胺的氨解

  摘要：

  报道了烯丙基酯与双锂酰胺的氨解。叔芳基酰胺与双锂酰胺和合适的亲电试剂通过一锅法合成，收率很高。用各种苯胺和氨基吡啶证明了该反应的范围，并将其用于三苯基甲基乙酰胺的合成。

  DOI：

  10.1016/j.tetlet.2006.07.136

文献信息

• Amine Activation: Synthesis of <i>N</i>-(Hetero)arylamides from Isothioureas and Carboxylic Acids
  作者：Yan-Ping Zhu、Sergey Sergeyev、Philippe Franck、Romano V. A. Orru、Bert U. W. Maes

  DOI：10.1021/acs.orglett.6b02247

  日期：2016.9.16

  A novel method for N-(hetero)arylamide synthesis based on rarely explored amine activation, rather than classical acid activation, is reported. The activated amines are easily prepared using a three-component reaction with commercial reagents. The new method shows a broad scope including challenging amides not (efficiently) accessible via classical protocols.

  报道了基于很少探索的胺活化而不是经典的酸活化的N-（杂）芳基酰胺合成的新方法。使用三组分反应与市售试剂可轻松制备活化的胺。新方法显示出广泛的应用范围，包括无法（有效）通过经典方案获得的具有挑战性的酰胺。
• A protocol for amide bond formation with electron deficient amines and sterically hindered substrates
  作者：Maria E. Due-Hansen、Sunil K. Pandey、Elisabeth Christiansen、Rikke Andersen、Steffen V. F. Hansen、Trond Ulven

  DOI：10.1039/c5ob02129d

  日期：——

  A protocol for amide coupling by in situ formation of acyl fluorides and reaction with amines at elevated temperature has been developed and found to be efficient for coupling of sterically hindered substrates and electron deficient amines where standard methods failed.

  已开发出一种酰氟体系偶联的方法，通过在高温下原位生成酰氟化合物并与胺发生反应，发现该方法对于难以偶联的底物和电子亏缺的胺具有高效率，而标准方法无法胜任。
• Synthesis and Identification of Small Molecules that Potently Induce Apoptosis in Melanoma Cells through G1 Cell Cycle Arrest
  作者：Robin S. Dothager、Karson S. Putt、Brittany J. Allen、Benjamin J. Leslie、Vitaliy Nesterenko、Paul J. Hergenrother

  DOI：10.1021/ja042913p

  日期：2005.6.1

  Late-stage malignant melanoma is a cancer that is refractory to current chemotherapeutic treatments. The average survival time for patients with such a diagnosis is 6 months. In general, the vast majority of anticancer drugs operate through induction of cell cycle arrest and cell death in either the DNA synthesis (S) or mitosis (M) phase of the cell cycle. Unfortunately, the same mechanisms that melanocytes possess to protect cells from DNA damage often confer resistance to drugs that derive their toxicity from S or M phase arrest. Described herein is the synthesis of a combinatorial library of potential proapoptotic agents and the subsequent identification of a class of small molecules (triphenyl methylamides, TPMAs) that arrest the growth of melanoma cells in the G1 phase of the cell cycle. Several of these TPMAs are quite potent inducers of apoptotic death in melanoma cell lines (IC50 similar to 0.5 mu M), and importantly, some TPMAs are comparatively nontoxic to normal cells isolated from the bone marrow of healthy donors. Furthermore, the TPMAs were found to dramatically reduce the level of active nuclear factor kappa-B (NF kappa B) in the cell; NF kappa B is known to be constitutively active in melanoma, and this activity is critical for the proliferation of melanoma cells and their evasion of apoptosis. Compounds that reduce the level of NF kappa B and arrest cells in the G1 phase of the cell cycle can provide insights into the biology of melanoma and may be effective antimelanoma agents.