2-(4-chlorophenyl)-5-(4-methoxyphenyl)-2,4-Dihydro-3H-pyrazol-3-one | 60798-16-5

• 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: 2-(4-chlorophenyl)-5-(4-methoxyphenyl)-2,4-Dihydro-3H-pyrazol-3-one
• 英文别名: 2-(4-chloro-phenyl)-5-(4-methoxy-phenyl)-1,2-dihydro-pyrazol-3-one；1-(p-Chlorphenylen)-3-(p-anisyl)-pyrazolon-(5)
• CAS: 60798-16-5
• 化学式: C₁₆H₁₃ClN₂O₂
• 分子量: 300.744
• InChiKey: JSEKSDDXCBSFNL-UHFFFAOYSA-N

物化性质

• 熔点：
  143-144 °C
• 沸点：
  443.5±55.0 °C(Predicted)
• 密度：
  1.29±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.49
• 重原子数：
  21.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  41.9
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  乙烯磺酰氟 、 2-(4-chlorophenyl)-5-(4-methoxyphenyl)-2,4-Dihydro-3H-pyrazol-3-one 在 碳酸氢钠 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以61%的产率得到7-(4-chlorophenyl)-5-(4-methoxyphenyl)-4,7-dihydro-3H-[1,2]oxathiino[6,5-c]pyrazole 2,2-dioxide
  参考文献：
  名称：

  The structure-based optimization of δ-sultone-fused pyrazoles as selective BuChE inhibitors

  摘要：

  Structure-based optimization was conducted to improve the potency and selectivity of BuChE inhibitors with delta-sulfonolactone-fused pyrazole scaffold. By mimicking the hydrophobic interactions of donepezil at PAS, the introduction of a tertiary benzylamine at 5-position can significantly increase BuChE inhibitory activity. Compounds C4 and C6 were identified as high selective nanomolar BuChE inhibitors (IC50 = 8.3 and 7.7 nM, respectively), which exhibited mild antioxidant capacity, nontoxicity, lipophilicity and neuroprotective activity. Kinetic studies showed that BuChE inhibition of compound C6 was mixed-type against BuChE (K-i = 24 nM) and >2000-fold selectivity for BuChE over AChE. The proposed binding mode of new inhibitors was consistent with the results of structure-activity relationship analysis. (C) 2020 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2020.112273
• 作为产物：
  描述：

  对氯苯肼盐酸盐 、 3-(4-甲氧苯基)-3-氧代丙酸乙酯 在 sodium ethanolate 作用下， 以 乙醇 为溶剂， 反应 3.0h， 以73%的产率得到2-(4-chlorophenyl)-5-(4-methoxyphenyl)-2,4-Dihydro-3H-pyrazol-3-one
  参考文献：
  名称：

  从取代肼和 β-酮酯合成四取代吡唑

  摘要：

  在此，我们报告了在温和、碱性条件下从简单的肼和 β-酮酯合成四取代的吡唑。该反应能够选择性合成吡唑啉酮、烷氧基吡唑和四取代吡唑，以高产率和选择性地合成多种芳香肼和取代 β-酮酯。这种方法允许使用具有四个正交多样化组的高度复杂的吡唑支架。

  DOI：

  10.1002/ejoc.201601093

文献信息

• Synthesis of Tetrasubstituted Pyrazoles from Substituted Hydrazines and β-Keto Esters
  作者：Ian J. Bakanas、Gustavo Moura-Letts

  DOI：10.1002/ejoc.201601093

  日期：2016.11

  Herein we report the synthesis of tetrasubstituted pyrazoles from simple hydrazines and β-keto esters under mild, basic conditions. This reaction enables the selective synthesis of pyrazolones, alkoxypyrazoles, and tetrasubstituted pyrazoles for a large variety of aromatic hydrazines and substituted β-keto esters with high yields and selectivities. This method permits access to highly complex pyrazole

  在此，我们报告了在温和、碱性条件下从简单的肼和 β-酮酯合成四取代的吡唑。该反应能够选择性合成吡唑啉酮、烷氧基吡唑和四取代吡唑，以高产率和选择性地合成多种芳香肼和取代 β-酮酯。这种方法允许使用具有四个正交多样化组的高度复杂的吡唑支架。
• The structure-based optimization of δ-sultone-fused pyrazoles as selective BuChE inhibitors
  作者：Ziwen Zhang、Jingli Min、Mengdie Chen、Xia Jiang、Yingying Xu、Huali Qin、Wenjian Tang

  DOI：10.1016/j.ejmech.2020.112273

  日期：2020.9

  Structure-based optimization was conducted to improve the potency and selectivity of BuChE inhibitors with delta-sulfonolactone-fused pyrazole scaffold. By mimicking the hydrophobic interactions of donepezil at PAS, the introduction of a tertiary benzylamine at 5-position can significantly increase BuChE inhibitory activity. Compounds C4 and C6 were identified as high selective nanomolar BuChE inhibitors (IC50 = 8.3 and 7.7 nM, respectively), which exhibited mild antioxidant capacity, nontoxicity, lipophilicity and neuroprotective activity. Kinetic studies showed that BuChE inhibition of compound C6 was mixed-type against BuChE (K-i = 24 nM) and >2000-fold selectivity for BuChE over AChE. The proposed binding mode of new inhibitors was consistent with the results of structure-activity relationship analysis. (C) 2020 Elsevier Masson SAS. All rights reserved.