4-chloro-5-(3-chloro-2,6-difluorophenyl)-1-(4-chlorophenyl)-2-methyl-1H-imidazole | 1193349-04-0

• 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-chloro-5-(3-chloro-2,6-difluorophenyl)-1-(4-chlorophenyl)-2-methyl-1H-imidazole
• 英文别名: 5-(3-chloro-2,6-difluorophenyl)-1-(4-chlorophenyl)-2-methyl-4-chloro-1H-imidazole；4-Chloro-5-(3-chloro-2,6-difluorophenyl)-1-(4-chlorophenyl)-2-methylimidazole
• CAS: 1193349-04-0
• 化学式: C₁₆H₉Cl₃F₂N₂
• 分子量: 373.617
• InChiKey: MBRZYNLDECLOLS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  17.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (E)-1-(3-chloro-2,6-difluorophenyl)-N-(4-chlorophenyl)methanimine 在 N-氯代丁二酰亚胺 、 potassium carbonate 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 乙二醇二甲醚 、 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 反应 33.5h， 生成 4-chloro-5-(3-chloro-2,6-difluorophenyl)-1-(4-chlorophenyl)-2-methyl-1H-imidazole
  参考文献：
  名称：

  Multitargeted Imidazoles: Potential Therapeutic Leads for Alzheimer’s and Other Neurodegenerative Diseases

  摘要：

  Alzheimer's disease (AD) is a complex, multifactorial disease in which different neuropathological mechanisms are likely involved, including those associated with pathological tau and A beta species as well as neuroinflammation. In this context, the development of single multitargeted therapeutics directed against two or more disease mechanisms could be advantageous. Starting from a series of 1,5-diarylimidazoles with microtubule (MT)-stabilizing activity and structural similarities with known NSALDs, we conducted structure-activity relationship studies that led to the identification of multitargeted prototypes with activities as MT-stabilizing agents and/or inhibitors of the cyclooxygenase (COX) and 5-lipoxygenase (5-LOX) pathways. Several examples are brain-penetrant and exhibit balanced multitargeted in vitro activity in the low mu M range. As brain-penetrant MT-stabilizing agents have proven effective against tau-mediated neurodegeneration in animal models, and because COX- and 5-LOX-derived eicosanoids are thought to contribute to A beta plaque deposition, these 1,5-diarylimidazoles provide tools to explore novel multitargeted strategies for AD and other neurodegenerative diseases.

  DOI：

  10.1021/acs.jmedchem.7b00475