2-amino-4-(3-bromophenyl)-6-[1-methyl-2-(morpholin-4-yl)-1H-imidazol-4-yl]nicotinonitrile | 856014-44-3

• 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-4-(3-bromophenyl)-6-[1-methyl-2-(morpholin-4-yl)-1H-imidazol-4-yl]nicotinonitrile
• CAS: 856014-44-3
• 化学式: C₂₀H₁₉BrN₆O
• 分子量: 439.314
• InChiKey: JDDSHNQFCIJIGB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  28.0
• 可旋转键数：
  3.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  92.99
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  2-amino-4-(3-bromophenyl)-6-[1-methyl-2-(morpholin-4-yl)-1H-imidazol-4-yl]nicotinonitrile 在 ammonium sulfate 、 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 2.0h， 生成 5-(3-Bromo-phenyl)-7-(1-methyl-2-morpholin-4-yl-1H-imidazol-4-yl)-pyrido[2,3-d]pyrimidin-4-ylamine
  参考文献：
  名称：

  5-(3-Bromophenyl)-7-(6-morpholin-4-ylpyridin-3-yl)pyrido[2,3-d]pyrimidin-4-ylamine: structure–activity relationships of 7-substituted heteroaryl analogs as non-nucleoside adenosine kinase inhibitors

  摘要：

  4-Amino-5,7-disubstituted pyridopyrimidines are potent, non-nucleoside inhibitors of adenosine kinase (AK). We recently identified a potent, orally efficacious analog, 4 containing a 7-pyridylmorpholine substituted ring system as the key structural element of this template. In this report, we disclose the pharmacologic effects of five- and six-membered heterocyclic ring replacements for the pyridine ring in 4. These replacements were found to have interesting effects on in vivo efficacy and genotoxicity as well as in vitro potency. We discovered that the nitrogen in the heterocyclic ring at C(7) is important for the modulation of mutagenic side effects (Ames assay). (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.03.023
• 作为产物：
  描述：

  1-(2-吗啉-4-基-1H-咪唑-5-基)乙酮 在 乙酸铵 、 sodium hydride 作用下， 以 四氢呋喃 、 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.5h， 生成 2-amino-4-(3-bromophenyl)-6-[1-methyl-2-(morpholin-4-yl)-1H-imidazol-4-yl]nicotinonitrile
  参考文献：
  名称：

  5-(3-Bromophenyl)-7-(6-morpholin-4-ylpyridin-3-yl)pyrido[2,3-d]pyrimidin-4-ylamine: structure–activity relationships of 7-substituted heteroaryl analogs as non-nucleoside adenosine kinase inhibitors

  摘要：

  4-Amino-5,7-disubstituted pyridopyrimidines are potent, non-nucleoside inhibitors of adenosine kinase (AK). We recently identified a potent, orally efficacious analog, 4 containing a 7-pyridylmorpholine substituted ring system as the key structural element of this template. In this report, we disclose the pharmacologic effects of five- and six-membered heterocyclic ring replacements for the pyridine ring in 4. These replacements were found to have interesting effects on in vivo efficacy and genotoxicity as well as in vitro potency. We discovered that the nitrogen in the heterocyclic ring at C(7) is important for the modulation of mutagenic side effects (Ames assay). (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.03.023