{4-[(S)-2-(4-Fluoro-phenyl)-5-(4-methoxy-benzyloxymethyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl]-pyrimidin-2-yl}-propyl-amine | 869287-23-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: {4-[(S)-2-(4-Fluoro-phenyl)-5-(4-methoxy-benzyloxymethyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl]-pyrimidin-2-yl}-propyl-amine
• 英文别名: 2-Pyrimidinamine,4-[(5S)-2-(4-fluorophenyl)-6,7-dihydro-5-[[(4-methoxyphenyl)methoxy]methyl]-5H-pyrrolo[1,2-a]imidazol-3-yl]-N-propyl-；4-[(5S)-2-(4-fluorophenyl)-5-[(4-methoxyphenyl)methoxymethyl]-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl]-N-propylpyrimidin-2-amine
• CAS: 869287-23-0
• 化学式: C₂₈H₃₀FN₅O₂
• 分子量: 487.577
• InChiKey: HYYRJELYMNIRGB-QFIPXVFZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  36
• 可旋转键数：
  10
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  74.1
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  {4-[(S)-2-(4-Fluoro-phenyl)-5-(4-methoxy-benzyloxymethyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl]-pyrimidin-2-yl}-propyl-amine 在 盐酸 作用下， 以 甲醇 为溶剂， 生成 [(S)-2-(4-Fluoro-phenyl)-3-(2-propylamino-pyrimidin-4-yl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-5-yl]-methanol
  参考文献：
  名称：

  The neuroprotective action of JNK3 inhibitors based on the 6,7-dihydro-5H-pyrrolo[1,2-a]imidazole scaffold

  摘要：

  Imidazole-based structures of p38 inhibitors served as a starting point for the design of JNK3 inhibitors. Construction of a 6,7-dihydro-5H-pyrrolo[1,2-a]imidazole scaffold led to the synthesis of the (S)-enantiomers, which exhibited p38/JNK3 IC50 ratio of up to 10 and were up to 20 times more potent inhibitors of JNK3 than the relevant (R)-enantiomers. The JNK3 inhibitory potency correlated well with inhibition of c-Jun phosphorylation and neuroprotective properties of the compounds in low K+-induced cell death of rat cerebellar granule neurotics. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.07.076
• 作为产物：
  描述：

  (S)-5-[(tert-butyl)-diphenylsilyloxy-methyl]-2-thiopyrrolidinone 在 sodium hydroxide 、 正丁基锂 、 四丁基氟化铵 、 氢溴酸 、 双氧水 、 四丁基硫酸氢铵 、 氯化铵 、 溶剂黄146 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 187.5h， 生成 {4-[(S)-2-(4-Fluoro-phenyl)-5-(4-methoxy-benzyloxymethyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl]-pyrimidin-2-yl}-propyl-amine
  参考文献：
  名称：

  The neuroprotective action of JNK3 inhibitors based on the 6,7-dihydro-5H-pyrrolo[1,2-a]imidazole scaffold

  摘要：

  Imidazole-based structures of p38 inhibitors served as a starting point for the design of JNK3 inhibitors. Construction of a 6,7-dihydro-5H-pyrrolo[1,2-a]imidazole scaffold led to the synthesis of the (S)-enantiomers, which exhibited p38/JNK3 IC50 ratio of up to 10 and were up to 20 times more potent inhibitors of JNK3 than the relevant (R)-enantiomers. The JNK3 inhibitory potency correlated well with inhibition of c-Jun phosphorylation and neuroprotective properties of the compounds in low K+-induced cell death of rat cerebellar granule neurotics. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.07.076