{4-[5-(4-Chlorophenyl)-6-piperazin-1-ylpyrimidin-4-ylethynyl]phenyl}dimethylamine | 926009-37-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: {4-[5-(4-Chlorophenyl)-6-piperazin-1-ylpyrimidin-4-ylethynyl]phenyl}dimethylamine
• 英文别名: 4-[2-[5-(4-chlorophenyl)-6-piperazin-1-ylpyrimidin-4-yl]ethynyl]-N,N-dimethylaniline
• CAS: 926009-37-2
• 化学式: C₂₄H₂₄ClN₅
• 分子量: 417.941
• InChiKey: SWGSRRBUYDEWPG-UHFFFAOYSA-N

物化性质

• 沸点：
  652.1±55.0 °C(Predicted)
• 密度：
  1.30±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  30
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  44.3
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  {4-[5-(4-Chlorophenyl)-6-piperazin-1-ylpyrimidin-4-ylethynyl]phenyl}dimethylamine 、 二甲胺基磺酰氯 在 三乙胺 作用下， 以77%的产率得到4-[5-(4-chlorophenyl)-6-[2-[4-(dimethylamino)phenyl]ethynyl]pyrimidin-4-yl]-N,N-dimethylpiperazine-1-sulfonamide
  参考文献：
  名称：

  4-Amino-5-aryl-6-arylethynylpyrimidines: Structure–activity relationships of non-nucleoside adenosine kinase inhibitors

  摘要：

  A series of non-nucleoside adenosine kinase (AK) inhibitors is reported. These inhibitors originated from the modification of 5-(3-bromophenyl)-7-(6-morpholin-4-ylpyridin-3-yl)pyrido[2,3-d]pyrimidin-4-ylamine (ABT-702). The identification of a linker that would approximate the spatial arrangement found between the pyrimidine ring and the aryl group at C(7) in ABT702 was a key element in this modification. A search of potential linkers led to the discovery of an acetylene moiety as a suitable scaffold. It was hypothesized that the aryl acetylenes, ABT-702, and adenosine bound to the active site of AK (closed form) in a similar manner with respect to the orientation of the heterocyclic base. Although potent acetylene analogs were discovered based on this assumption, an X-ray crystal structure of 5-(4-dimethylaminophenyl)-6-(6-morpholin-4-yipyridin-3-ylethynyl)pyrimidin-4-ylamine (16a) revealed a binding orientation contrary to adenosine. In addition, this compound bound tightly to a unique open conformation of AK. The structure-activity relationships and unique ligand orientation and protein conformation are discussed. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.12.029
• 作为产物：
  描述：

  对氯苯乙酸 在 bis-triphenylphosphine-palladium(II) chloride 盐酸 、 copper(l) iodide 、 sodium methylate 、 sodium hydride 、 三乙胺 、 三氯氧磷 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 正己烷 、 乙腈 为溶剂， 反应 4.0h， 生成 {4-[5-(4-Chlorophenyl)-6-piperazin-1-ylpyrimidin-4-ylethynyl]phenyl}dimethylamine
  参考文献：
  名称：

  4-Amino-5-aryl-6-arylethynylpyrimidines: Structure–activity relationships of non-nucleoside adenosine kinase inhibitors

  摘要：

  A series of non-nucleoside adenosine kinase (AK) inhibitors is reported. These inhibitors originated from the modification of 5-(3-bromophenyl)-7-(6-morpholin-4-ylpyridin-3-yl)pyrido[2,3-d]pyrimidin-4-ylamine (ABT-702). The identification of a linker that would approximate the spatial arrangement found between the pyrimidine ring and the aryl group at C(7) in ABT702 was a key element in this modification. A search of potential linkers led to the discovery of an acetylene moiety as a suitable scaffold. It was hypothesized that the aryl acetylenes, ABT-702, and adenosine bound to the active site of AK (closed form) in a similar manner with respect to the orientation of the heterocyclic base. Although potent acetylene analogs were discovered based on this assumption, an X-ray crystal structure of 5-(4-dimethylaminophenyl)-6-(6-morpholin-4-yipyridin-3-ylethynyl)pyrimidin-4-ylamine (16a) revealed a binding orientation contrary to adenosine. In addition, this compound bound tightly to a unique open conformation of AK. The structure-activity relationships and unique ligand orientation and protein conformation are discussed. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.12.029