3-[2-(6-chloropyridazin-3-ylamino)phenylamino]-1H-pyrazol-5(4H)-one | 1593884-11-7

• 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: 3-[2-(6-chloropyridazin-3-ylamino)phenylamino]-1H-pyrazol-5(4H)-one
• 英文别名: 5-[2-[(6-Chloropyridazin-3-yl)amino]phenyl]iminopyrazolidin-3-one；5-[2-[(6-chloropyridazin-3-yl)amino]phenyl]iminopyrazolidin-3-one
• CAS: 1593884-11-7
• 化学式: C₁₃H₁₁ClN₆O
• 分子量: 302.723
• InChiKey: PHMLZENNCHXTEC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  91.3
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-[2-(6-chloropyridazin-3-ylamino)phenylamino]-1H-pyrazol-5(4H)-one 、 3-甲基苯胺 在 potassium carbonate 作用下， 以 正丁醇 为溶剂， 反应 4.0h， 以70%的产率得到3-{2-[6-(3-methylanilino)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
• 作为产物：
  描述：

  3,6-二氯哒嗪 、 5-[(2-aminophenyl)amino]-2,4-dihydro-3H-pyrazol-3-one 在 potassium carbonate 作用下， 以 异丙醇 为溶剂， 反应 4.0h， 以80%的产率得到3-[2-(6-chloropyridazin-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 and biological evaluation of new pyrazolone–pyridazine conjugates as anti-inflammatory and analgesic agents
  作者：Nadia Abdalla Khalil、Eman Mohamed Ahmed、Khaled Omar Mohamed、Yassin Mohammed Nissan、Sawsan Abo-Bakr Zaitone

  DOI：10.1016/j.bmc.2014.02.042

  日期：2014.4

  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.