2-chloro-4,6-bis-(4-methoxy-phenyl)-nicotinonitrile | 50549-05-8

• 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-chloro-4,6-bis-(4-methoxy-phenyl)-nicotinonitrile
• 英文别名: 2-Chloro-4,6-bis(4-methoxyphenyl)pyridine-3-carbonitrile
• CAS: 50549-05-8
• 化学式: C₂₀H₁₅ClN₂O₂
• 分子量: 350.804
• InChiKey: PODPGQAXFIZQKL-UHFFFAOYSA-N

物化性质

• 沸点：
  528.7±50.0 °C(Predicted)
• 密度：
  1.31±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  55.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-chloro-4,6-bis-(4-methoxy-phenyl)-nicotinonitrile 在 氢氧化钾 、 sodium ethanolate 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 22.0h， 生成 ethyl 3-amino-4,6-bis(4-methoxyphenyl)thieno[2,3-b]pyridine-2-carboxylate
  参考文献：
  名称：

  Dave, Chaitanya; Shah, P R; Shah, A B, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1992, vol. 31, # 8, p. 492 - 494

  摘要：

  DOI：
• 作为产物：
  描述：

  4,4’-二甲氧基查耳酮 在 potassium tert-butylate 、 三氯氧磷 作用下， 以 乙醇 为溶剂， 生成 2-chloro-4,6-bis-(4-methoxy-phenyl)-nicotinonitrile
  参考文献：
  名称：

  Second‐Generation CD73 Inhibitors Based on a 4,6‐Biaryl‐2‐thiopyridine Scaffold

  摘要：

  AbstractVarious series of 4,6‐biaryl‐2‐thiopyridine derivatives were synthesized and evaluated as potential ecto‐5′‐nucleotidase (CD73) inhibitors. Two synthetic routes were explored and the coupling of 4,6‐disubstituted 3‐cyano‐2‐chloro‐pyridines with selected thiols allowed us to explore the structural diversity. Somehow divergent results were obtained in biological assays on CD73 inhibition using either the purified recombinant protein or cell‐based assays, highlighting the difficulty to target protein‐protein interface on proteins existing as soluble and membrane‐bound forms. Among the 18 new derivatives obtained, three derivatives incorporating morpholino substituents on the 4,6‐biaryl‐2‐thiopyridine core were shown to be able to reverse the adenosine‐mediated immune suppression on human T cells. The higher blockade efficiency was observed for 2‐((3‐cyano‐4,6‐bis(4‐morpholinophenyl)pyridin‐2‐yl)thio)‐N‐(isoxazol‐3‐yl)acetamide (with total reversion at 100 μM) and methyl 2‐((3‐cyano‐4,6‐bis(4‐morpholinophenyl)pyridin‐2‐yl)thio)acetate (with partial reversion at 10 μM). Thus, this series of compounds illustrates a new chemotype of CD73 allosteric inhibitors.

  DOI：

  10.1002/cmdc.202200594

文献信息

• A simple and expedient method for the synthesis of ethyl 3-amino-4,6-diarylthieno[2,3-<i>b</i>]pyridine-2-carboxylate
  作者：Hetal C. Shah、Vaishali H. Shah、Nirmal D. Desai

  DOI：10.1002/jhet.237

  日期：2009.11

  2‐Chloro‐4,6‐diarylnicotinonitrile 1 was reacted with ethyl 2‐mercaptoacetate 2 to furnish ethyl 2‐(3‐cyano‐4,6‐diarylpyridin‐2‐ylthio)acetate 3 as intermediates. These intermediates were cyclized by Thorpe–Zeigler cyclization using solid–liquid phase‐transfer catalysis conditions to give ethyl 3‐amino‐4,6‐diarylthieno[2,3‐b]pyridine‐2‐carboxylate 4. One‐pot heterocyclization without isolating the

  2-氯-4,6- diarylnicotinonitrile 1用2-巯基乙酸乙酯进行反应2至配料中的2-（3-氰基-4,6- diarylpyridin -2-基硫基）乙酸甲酯3作为中间体。这些中间体通过固-液相转移催化条件通过Thorpe–Zeigler环化环化，得到3-氨基-4-6,6-二芳基噻吩并[2,3 - b ]吡啶-2-羧酸乙酯4。使用固液相转移条件也可以实现不分离中间体的单锅杂环。J.杂环化​​学，（2009）。
• Multi-targeted anti-Alzheimer's agents: Synthesis, biological evaluation, and molecular modeling study of some pyrazolopyridine hybrids
  作者：Omnia M. Waly、Selwan M. El-Sayed、Mariam A. Ghaly、Hussein I. El-Subbagh

  DOI：10.1016/j.ejmech.2023.115880

  日期：2023.12