5-[(2-aminophenyl)amino]-2,4-dihydro-3H-pyrazol-3-one | 1271740-69-2

• 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: 5-[(2-aminophenyl)amino]-2,4-dihydro-3H-pyrazol-3-one
• 英文别名: 3-(2-aminophenylamino)-1H-pyrazol-5(4H)-one
• CAS: 1271740-69-2
• 化学式: C₉H₁₀N₄O
• 分子量: 190.205
• InChiKey: GBUSZMPPNATVMU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.51
• 重原子数：
  14.0
• 可旋转键数：
  1.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  79.51
• 氢给体数：
  3.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  5-[(2-aminophenyl)amino]-2,4-dihydro-3H-pyrazol-3-one 在 potassium carbonate 作用下， 以 异丙醇 、 正丁醇 为溶剂， 反应 8.0h， 生成 3-{2-[6-(3-nitroanilino)pyridazin-3-ylamino]phenylamino}-1H-pyrazol-5(4H)-one
  参考文献：
  名称：

  Synthesis and biological evaluation of new pyrazolone–pyridazine conjugates as anti-inflammatory and analgesic agents

  摘要：

  A new series of pyrazolone-pyridazine conjugates 3 and 4a-1 were synthesized and characterized by spectroscopic means and elemental analyses. All compounds were tested in vivo for their anti-inflammatory and analgesic properties against diclofenac, as reference compound. The synthesized compounds were also evaluated for their ability to inhibit the production of certain inflammatory cytokines such as TNF-alpha and IL-6 in serum samples. The ulcerogenic potential of the synthesized compounds was also determined. IC50 values for inhibition of COX-1 and COX-2 enzymes were investigated in vitro for the most active candidates. Molecular docking was performed on the active site of COX-2 to predict their mode of binding to the amino acids. Among the synthesized derivatives, compounds 4c and 4e showed good analgesic and anti-inflammatory activities with lower ulcer index than the reference drug. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2014.02.042

文献信息

• Synthesis of Novel Substituted Thiourea and Benzimidazole Derivatives Containing a Pyrazolone Ring as Anti-Inflammatory Agents
  作者：Ashraf A. Moneer、Khaled O. Mohammed、Hala B. El-Nassan

  DOI：10.1111/cbdd.12712

  日期：2016.5

  Two series of new 1‐(alkyl/aryl)‐3‐2‐[(5‐oxo‐4,5‐dihydro‐1H‐pyrazol‐3‐yl)amino]phenyl}thioureas 2a–h and 5‐[2‐(substituted amino)‐1H‐benzimidazol‐1‐yl]‐4H‐pyrazol‐3‐ols 3a–i were designed and synthesized as anti‐inflammatory agents. The cyclooxygenase inhibitory activity of the newly synthesized compounds was investigated. All the compounds showed non‐selective inhibition of COX‐1 and COX‐2 enzymes

  两个系列的新的1-（烷基/芳基）-3- 2-[（5-氧代-4,5-二氢-1 H-吡唑-3-基）氨基]苯基}硫脲2a – h和5– [设计并合成了2-（取代氨基）-1 H-苯并咪唑-1-基] -4 H-吡唑-3-醇3a – i作为抗炎药。研究了新合成化合物的环氧合酶抑制活性。所有化合物均显示出对COX-1和COX-2酶的非选择性抑制，这与它们的对接结果一致。化合物2c，2f，2g，3b和3g使用双氯芬酸作为参考药物，选择表现出最高COX-2抑制活性的化合物作为抗炎药进行进一步的体内测试。两种测试化合物（2c和3b）显示出与双氯芬酸相当的有效抗炎活性，并且相对于消炎痛而言具有更低的致溃疡作用。还提供了作为环加氧酶抑制剂和抗炎药的两个系列的SAR研究。