(5S)-2-(4-fluorophenyl)-5-[(4-methoxyphenyl)methoxymethyl]-3-(2-methylsulfanylpyrimidin-4-yl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazole | 471844-88-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: (5S)-2-(4-fluorophenyl)-5-[(4-methoxyphenyl)methoxymethyl]-3-(2-methylsulfanylpyrimidin-4-yl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazole
• CAS: 471844-88-9
• 化学式: C₂₆H₂₅FN₄O₂S
• 分子量: 476.575
• InChiKey: LOYBZAIAHWMELF-FQEVSTJZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  34
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  87.4
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (5S)-2-(4-fluorophenyl)-5-[(4-methoxyphenyl)methoxymethyl]-3-(2-methylsulfanylpyrimidin-4-yl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazole 在 盐酸 、 双氧水 、 溶剂黄146 作用下， 以 甲醇 为溶剂， 反应 48.0h， 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 、 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 139.5h， 生成 (5S)-2-(4-fluorophenyl)-5-[(4-methoxyphenyl)methoxymethyl]-3-(2-methylsulfanylpyrimidin-4-yl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazole
  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

文献信息

• Jun kinase inhibitors
  申请人：——

  公开号：US20040235864A1

  公开（公告）日：2004-11-25

  The present invention provides novel compounds of formula I 1 and their use in the inhibition of c-Jun N-terminal kinases. The present invention further provides the use of these compounds in medicine, in particular in the prevention and/or treatment of neurodegenerative disorders related to apoptosis and/or inflammation.

  本发明提供了I1式新化合物及其在抑制c-Jun N末端激酶中的应用。本发明还提供了这些化合物在医学上的应用，特别是在预防和/或治疗与细胞凋亡和/或炎症相关的神经退行性疾病方面的应用。
• US7314940B2
  申请人：——

  公开号：US7314940B2

  公开（公告）日：2008-01-01