3-(4-chlorophenyl)-1-methyl-5-phenyl-4,5-dihydro-1H-pyrazole | 1018817-73-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 3-(4-chlorophenyl)-1-methyl-5-phenyl-4,5-dihydro-1H-pyrazole
• 英文别名: 5-(4-Chlorophenyl)-2-methyl-3-phenyl-3,4-dihydropyrazole
• CAS: 1018817-73-6
• 化学式: C₁₆H₁₅ClN₂
• 分子量: 270.762
• InChiKey: KZDWLZNBRCQSNB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  15.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-(4-chlorophenyl)-1-methyl-5-phenyl-4,5-dihydro-1H-pyrazole 在 palladium on activated charcoal 溶剂黄146 作用下， 反应 6.0h， 以56%的产率得到1-methyl-3-(4-chlorophenyl)-5-phenylpyrazole
  参考文献：
  名称：

  Aryl azoles with neuroprotective activity—Parallel synthesis and attempts at target identification

  摘要：

  A parallel synthesis of aryl azoles with neuroprotective activity is described. All compounds obtained were evaluated in an in vitro assay using a NMDA toxicity paradigm showing a neuroprotective activity between 15% and 40%. The potential biological target of the active compounds was investigated by extensive literature searches based around similar scaffolds with reported neuroprotective activity. The most interesting molecules active in the NMDA toxicity assay (3a and 2g) showed moderate but significant activity in the inhibition of the Site 2 Sodium Channel binding assay at 10 mu M. To confirm our hypothesis compounds 3a, c, f and 2g were tested in the Veratridine assay which is one of the excitotoxicity assays of revelance to NaV channels. The compounds tested showed an activity between 40% and 70%. The identification of neuroprotective small molecules and the identification of NaV channels as the potential site of action were the most important goals of this work. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.10.090
• 作为产物：
  描述：

  甲基肼 、 4'-chlorochalcone 以 1,4-二氧六环 为溶剂， 反应 1.0h， 生成 3-(4-chlorophenyl)-1-methyl-5-phenyl-4,5-dihydro-1H-pyrazole
  参考文献：
  名称：

  吡唑啉和吡唑的直接合成：钯催化的芳基卤化物羰基化乙烯基化-环缩聚反应

  摘要：

  已经建立了一种以简单的芳基卤化物、苯乙烯、一氧化碳和肼为原料连续一锅法合成吡唑啉和吡唑的方法。钯催化的芳基卤化物羰基化乙烯基化得到相应的查耳酮，通过加入肼原位捕获。

  DOI：

  10.1002/ejoc.201100654

文献信息

• A Straightforward Synthesis of Pyrazolines and Pyrazoles: Palladium-Catalyzed Carbonylative Vinylation-Cyclocondensation Reactions of Aryl Halides
  作者：Xiao-Feng Wu、Helfried Neumann、Matthias Beller

  DOI：10.1002/ejoc.201100654

  日期：2011.7.19

  A novel consecutive one-pot synthesis of pyrazolines and pyrazoles starting from simple aryl halides, styrenes, carbon monoxide, and hydrazines has been established. Palladium-catalyzed carbonylative vinylation of aryl halides gave the corresponding chalcones, which are trapped in situ by addition of hydrazines.

  已经建立了一种以简单的芳基卤化物、苯乙烯、一氧化碳和肼为原料连续一锅法合成吡唑啉和吡唑的方法。钯催化的芳基卤化物羰基化乙烯基化得到相应的查耳酮，通过加入肼原位捕获。
• Aryl azoles with neuroprotective activity—Parallel synthesis and attempts at target identification
  作者：Giuseppe Cocconcelli、Enrica Diodato、Andrea Caricasole、Giovanni Gaviraghi、Eva Genesio、Chiara Ghiron、Letizia Magnoni、Elena Pecchioli、Pier Vincenzo Plazzi、Georg C. Terstappen

  DOI：10.1016/j.bmc.2007.10.090

  日期：2008.2.15

  A parallel synthesis of aryl azoles with neuroprotective activity is described. All compounds obtained were evaluated in an in vitro assay using a NMDA toxicity paradigm showing a neuroprotective activity between 15% and 40%. The potential biological target of the active compounds was investigated by extensive literature searches based around similar scaffolds with reported neuroprotective activity. The most interesting molecules active in the NMDA toxicity assay (3a and 2g) showed moderate but significant activity in the inhibition of the Site 2 Sodium Channel binding assay at 10 mu M. To confirm our hypothesis compounds 3a, c, f and 2g were tested in the Veratridine assay which is one of the excitotoxicity assays of revelance to NaV channels. The compounds tested showed an activity between 40% and 70%. The identification of neuroprotective small molecules and the identification of NaV channels as the potential site of action were the most important goals of this work. (c) 2007 Elsevier Ltd. All rights reserved.