1-[5-(4-Nitrophenyl)-3-phenyl-3,4-dihydropyrazol-2-yl]ethanone | 313670-92-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-[5-(4-Nitrophenyl)-3-phenyl-3,4-dihydropyrazol-2-yl]ethanone
• CAS: 313670-92-7
• 化学式: C₁₇H₁₅N₃O₃
• 分子量: 309.324
• InChiKey: LQSFJJZRJMZZFH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  78.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-[5-(4-Nitrophenyl)-3-phenyl-3,4-dihydropyrazol-2-yl]ethanone 、 水杨醛 、 丙二腈 在 ammonium acetate 作用下， 以 乙醇 为溶剂， 反应 10.0h， 以57%的产率得到2-amino-4-(2-hydroxyphenyl)-6-[3-(4-nitrophenyl)-5-phenyl-4,5-dihydropyrazol-1-yl]nicotinonitrile
  参考文献：
  名称：

  Anticonvulsant Activity of a Combined Pharmacophore of Pyrazolo-pyridines with Lesser Toxicity in Mice

  摘要：

  设计并合成了多种2-氨基-6-[3-(取代苯基)-5-苯基-4,5-二氢吡唑-1-基]-4-(取代苯基)氮杂喹啉腌酸盐（3a-t），通过组合两种活性抗癫痫药物结构单元吡唑和吡啶。所有合成的化合物都具备良好抗癫痫活性所需的药效团元素。抗癫痫筛选通过最大电震抽搐（MES）和皮下戊二脳（scPTZ）测试进行。化合物3i和3s在这两项筛选中均显示出显著的抗癫痫活性，其在MES筛选中的$ED_{50}$值分别为17.5 mg/kg和22.6 mg/kg，在scPTZ筛选中分别为154.1 mg/kg和242.6 mg/kg。在较高剂量下测试时，它们在小鼠中也未显示出急性毒性效果。

  DOI：

  10.5012/bkcs.2011.32.2.576
• 作为产物：
  描述：

  苯甲醛 在 一水合肼 、 sodium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 反应 5.5h， 生成 1-[5-(4-Nitrophenyl)-3-phenyl-3,4-dihydropyrazol-2-yl]ethanone
  参考文献：
  名称：

  Anticonvulsant Activity of a Combined Pharmacophore of Pyrazolo-pyridines with Lesser Toxicity in Mice

  摘要：

  设计并合成了多种2-氨基-6-[3-(取代苯基)-5-苯基-4,5-二氢吡唑-1-基]-4-(取代苯基)氮杂喹啉腌酸盐（3a-t），通过组合两种活性抗癫痫药物结构单元吡唑和吡啶。所有合成的化合物都具备良好抗癫痫活性所需的药效团元素。抗癫痫筛选通过最大电震抽搐（MES）和皮下戊二脳（scPTZ）测试进行。化合物3i和3s在这两项筛选中均显示出显著的抗癫痫活性，其在MES筛选中的$ED_{50}$值分别为17.5 mg/kg和22.6 mg/kg，在scPTZ筛选中分别为154.1 mg/kg和242.6 mg/kg。在较高剂量下测试时，它们在小鼠中也未显示出急性毒性效果。

  DOI：

  10.5012/bkcs.2011.32.2.576

文献信息

• Amine‐functionalized nano‐NaY zeolite for the synthesis of <i>N</i> ‐acetyl pyrazoles and dihydropyrimidines
  作者：Raheleh Razavian Mofrad、Hassan Kabirifard、Mahmood Tajbakhsh、Ghasem Firouzzadeh Pasha

  DOI：10.1002/aoc.6383

  日期：2021.11

  An efficient base-catalyzed synthesis of dihydropyrimidines and N-acetyl pyrazoles is reported using 1-(2-aminoethyl)piperazine-modified nano-NaY zeolite (ZeSi–AP) under mild and green conditions. The structure of the catalyst was identified by using FT-IR, XRD, TGA, DTA, DLS, SEM, TEM, and elemental analyses. This heterogeneous catalyst has many benefits, such as a simple work-up procedure, high product

  据报道，在温和和绿色条件下，使用 1-（2-氨基乙基）哌嗪改性的纳米 NaY 沸石（ZeSi-AP）有效地碱催化合成二氢嘧啶和N-乙酰基吡唑。通过使用FT-IR、XRD、TGA、DTA、DLS、SEM、TEM和元素分析确定了催化剂的结构。这种非均相催化剂具有许多优点，例如后处理程序简单，产品收率高，并且易于再生和重复使用至少四个循环而不会失去其活性。
• 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.
• Anticonvulsant Activity of a Combined Pharmacophore of Pyrazolo-pyridines with Lesser Toxicity in Mice
  作者：Nadeem Siddiqui、Waquar Ahsan、M Shamsher Alam、Ruhi Ali、Kamna Srivastava、Sharique Ahmed

  DOI：10.5012/bkcs.2011.32.2.576

  日期：2011.2.20

  Various 2-amino-6-[3-(substituted phenyl)-5-phenyl-4,5-dihydropyrazol-1-yl]-4-(substituted phenyl)nicotinonitriles (3a-t) were designed and synthesized by clubbing two active anticonvulsant pharmacophores pyrazole and pyridine. All the synthesized compounds possessed the pharmacophoric elements essential for good anticonvulsant activity. The anticonvulsant screening was performed by maximal electroshock seizure (MES) and subcutaneous pentylenetetrazole (scPTZ) tests. Two compounds 3i and 3s showed significant anticonvulsant activity in both the screens with $ED_50}$ values 17.5 mg/kg and 22.6 mg/kg respectively in MES screen and 154.1 mg/kg and 242.6 mg/kg respectively in scPTZ screen. They were also found to have no acute toxic effects in mice when tested at elevated doses.

  设计并合成了多种2-氨基-6-[3-(取代苯基)-5-苯基-4,5-二氢吡唑-1-基]-4-(取代苯基)氮杂喹啉腌酸盐（3a-t），通过组合两种活性抗癫痫药物结构单元吡唑和吡啶。所有合成的化合物都具备良好抗癫痫活性所需的药效团元素。抗癫痫筛选通过最大电震抽搐（MES）和皮下戊二脳（scPTZ）测试进行。化合物3i和3s在这两项筛选中均显示出显著的抗癫痫活性，其在MES筛选中的$ED_50}$值分别为17.5 mg/kg和22.6 mg/kg，在scPTZ筛选中分别为154.1 mg/kg和242.6 mg/kg。在较高剂量下测试时，它们在小鼠中也未显示出急性毒性效果。