5-(3-bromo-2,6-difluorophenyl)-4-chloro-1-(4-chlorophenyl)-1H-imidazole | 1193348-29-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 5-(3-bromo-2,6-difluorophenyl)-4-chloro-1-(4-chlorophenyl)-1H-imidazole
• 英文别名: 4-chloro-1-(4-chlorophenyl)-5-(2,6-difluoro-3-bromophenyl)-1H-imidazole；5-(3-bromo-2,6-difluorophenyl)-4-chloro-1-(4-chlorophenyl)imidazole
• CAS: 1193348-29-6
• 化学式: C₁₅H₇BrCl₂F₂N₂
• 分子量: 404.041
• InChiKey: WTCPPEFJRKCQLR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  17.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-(3-bromo-2,6-difluorophenyl)-4-chloro-1-(4-chlorophenyl)-1H-imidazole 在 1,1'-双(二苯膦基)二茂铁二氯化钯(II)二氯甲烷复合物 N-溴代丁二酰亚胺(NBS) 、 四甲基乙二胺 作用下， 以 异丁酰胺 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.08h， 生成 3-[2-bromo-4-chloro-1-(4-chlorophenyl)-1H-imidazol-5-yl]-2,4-difluorobenzonitrile
  参考文献：
  名称：

  FUNGICIDAL SUBSTITUTED AZOLES

  摘要：

  揭示了公式1的化合物，包括所有的几何和立体异构体，N-氧化物和盐，其中J是Q2或R1；X是N，CR2或CQ3；Y是N或CR3；Z是N或CR4；Q1，Q2，Q3，R1，R2和R3如披露中定义的。还披露了含有公式1化合物的组合物以及控制由真菌病原体引起的植物疾病的方法，包括施用本发明的化合物或组合物的有效量。

  公开号：

  US20110045101A1
• 作为产物：
  描述：

  5-(3-bromo-2,6-difluorophenyl)-1-(4-chlorophenyl)-1H-imidazole 在 N-氯代丁二酰亚胺 作用下， 以 氯仿 为溶剂， 反应 16.0h， 以45%的产率得到5-(3-bromo-2,6-difluorophenyl)-4-chloro-1-(4-chlorophenyl)-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

文献信息

• [EN] FUNGICIDAL SUBSTITUTED AZOLES<br/>[FR] AZOLES SUBSTITUÉS FONGICIDES
  申请人：DU PONT

  公开号：WO2009137538A3

  公开（公告）日：2012-04-19
• [EN] FUNGICIDAL MIXTURES<br/>[FR] MÉLANGES FONGICIDES
  申请人：DU PONT

  公开号：WO2011056463A4

  公开（公告）日：2011-11-17
• Multitargeted Imidazoles: Potential Therapeutic Leads for Alzheimer’s and Other Neurodegenerative Diseases
  作者：Anne-Sophie Cornec、Ludovica Monti、Jane Kovalevich、Vishruti Makani、Michael J. James、Krishna G. Vijayendran、Killian Oukoloff、Yuemang Yao、Virginia M.-Y. Lee、John Q. Trojanowski、Amos B. Smith、Kurt R. Brunden、Carlo Ballatore

  DOI：10.1021/acs.jmedchem.7b00475

  日期：2017.6.22

  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.
• FUNGICIDAL SUBSTITUTED AZOLES
  申请人：Selby Thomas Paul

  公开号：US20110045101A1

  公开（公告）日：2011-02-24

  Disclosed are compounds of Formula 1, including all geometric and stereoisomers, N-oxides, and salts thereof, wherein J is Q 2 or R 1 ; X is N, CR 2 or CQ 3 ; Y is N or CR 3 ; Z is N or CR 4 ; and Q 1 , Q 2 , Q 3 , R 1 R 2 and R 3 are as defined in the disclosure. Also disclosed are compositions containing the compounds of Formula 1 and methods for controlling plant disease caused by a fungal pathogen comprising applying an effective amount of a compound or a composition of the invention.

  揭示了公式1的化合物，包括所有的几何和立体异构体，N-氧化物和盐，其中J是Q2或R1；X是N，CR2或CQ3；Y是N或CR3；Z是N或CR4；Q1，Q2，Q3，R1，R2和R3如披露中定义的。还披露了含有公式1化合物的组合物以及控制由真菌病原体引起的植物疾病的方法，包括施用本发明的化合物或组合物的有效量。