5-(3-chlorophenyl)-1-methyl-3-phenyl-4,5-dihydro-1H-pyrazole | 1018817-74-7

• 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-chlorophenyl)-1-methyl-3-phenyl-4,5-dihydro-1H-pyrazole
• 英文别名: 3-(3-Chlorophenyl)-2-methyl-5-phenyl-3,4-dihydropyrazole；3-(3-chlorophenyl)-2-methyl-5-phenyl-3,4-dihydropyrazole
• CAS: 1018817-74-7
• 化学式: C₁₆H₁₅ClN₂
• 分子量: 270.762
• InChiKey: SZYNJYNLKVJZCG-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：

  5-(3-chlorophenyl)-1-methyl-3-phenyl-4,5-dihydro-1H-pyrazole 在 palladium on activated charcoal 溶剂黄146 作用下， 反应 6.0h， 以55%的产率得到5-(3-chloro-phenyl)-1-methyl-3-phenyl-1H-pyrazole
  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：

  3-(3-chlorophenyl)-1-phenylprop-2-en-1-one 、 甲基肼 在 potassium hydroxide 作用下， 以 乙醇 为溶剂， 反应 24.0h， 以13%的产率得到5-(3-chlorophenyl)-1-methyl-3-phenyl-4,5-dihydro-1H-pyrazole
  参考文献：
  名称：

  设计，合成和体外对某些1-甲基-3,5-二苯基-4,5-二氢-1 H-吡唑类化合物的hMAO-B抑制性评估

  摘要：

  设计，合成了一系列1-甲基-3,5-二苯基-4,5-二氢-1 H-吡唑类化合物（3a - k和4a - u），并评估了它们对两种hMAO同工型的抑制作用。发现大多数衍生物是有效的和选择性的hMAO-B抑制剂。尤其是，衍生物3g与选择性抑制剂司来吉兰相比具有更高的hMAO-B亲和力，并具有高选择性指数（SI = 145）。最具选择性的hMAO-B抑制剂是3-甲基类似物3f，SI高于909。

  DOI：

  10.1016/j.bmcl.2013.07.035

文献信息

• Design, synthesis, and in vitro hMAO-B inhibitory evaluation of some 1-methyl-3,5-diphenyl-4,5-dihydro-1H-pyrazoles
  作者：Rossella Fioravanti、Nicoletta Desideri、Mariangela Biava、Luca Proietti Monaco、Laura Grammatica、Matilde Yáñez

  DOI：10.1016/j.bmcl.2013.07.035

  日期：2013.9

  A series of 1-methyl-3,5-diphenyl-4,5-dihydro-1H-pyrazoles (3a–k and 4a–u) were designed, synthesized, and evaluated for their inhibitory efficacy towards the two hMAO isoforms. Most of the derivatives were found to be potent and selective hMAO-B inhibitors. In particular, derivative 3g showed greater hMAO-B affinity than selective inhibitor selegiline coupled with high selectivity index (SI = 145)

  设计，合成了一系列1-甲基-3,5-二苯基-4,5-二氢-1 H-吡唑类化合物（3a - k和4a - u），并评估了它们对两种hMAO同工型的抑制作用。发现大多数衍生物是有效的和选择性的hMAO-B抑制剂。尤其是，衍生物3g与选择性抑制剂司来吉兰相比具有更高的hMAO-B亲和力，并具有高选择性指数（SI = 145）。最具选择性的hMAO-B抑制剂是3-甲基类似物3f，SI高于909。
• 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.