N'-(3-chlorobenzylidene)-2-(7-benzyl-3-methyl-4-oxoisoxazolo[4,5-d]pyridazin-4(5H)-yl)acetohydrazide | 1229043-30-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: N'-(3-chlorobenzylidene)-2-(7-benzyl-3-methyl-4-oxoisoxazolo[4,5-d]pyridazin-4(5H)-yl)acetohydrazide
• 英文别名: 2-(7-benzyl-3-methyl-4-oxo-[1,2]oxazolo[4,5-d]pyridazin-5-yl)-N-[(3-chlorophenyl)methylideneamino]acetamide
• CAS: 1229043-30-4
• 化学式: C₂₂H₁₈ClN₅O₃
• 分子量: 435.87
• InChiKey: NOGTVPTXCQDTLK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.09
• 重原子数：
  31.0
• 可旋转键数：
  6.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  102.38
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为产物：
  描述：

  2-(7-benzyl-3-methyl-4-oxoisoxazolo[4,5-d]pyridazin-4(5H)-yl)acetohydrazide 、 3-氯苯甲醛 在 盐酸 作用下， 以 乙醇 为溶剂， 以87%的产率得到N'-(3-chlorobenzylidene)-2-(7-benzyl-3-methyl-4-oxoisoxazolo[4,5-d]pyridazin-4(5H)-yl)acetohydrazide
  参考文献：
  名称：

  Synthesis and cyclooxygenase inhibitory activities of some N-acylhydrazone derivatives of isoxazolo[4,5-d]pyridazin-4(5H)-ones

  摘要：

  In this study, new isoxazolo[4,5-d]pyridazin-4(5H)-one derivatives having an N-acylhydrazone moiety were synthesized. The compounds were tested for their COX inhibitory activities using NS-398 and indomethacine as reference compounds. Although the compounds had an inhibitory profile against both COX-1 and COX-2, most were found to be more selective against COX-2 by a small percentage of inhibition, at the concentration of 50 mu M. Docking studies were clone to understand the interactions of the tested compounds with the active site of COX-2. It was observed that the compounds fit into, and interacted with, the hydrophobic parts which are common in the active pocket of COX-1 and COX-2 enzymes but could not fit to the area which is specific for COX-2 enzyme.

  DOI：

  10.1016/j.ejmech.2010.02.012

文献信息

• Synthesis and cyclooxygenase inhibitory activities of some N-acylhydrazone derivatives of isoxazolo[4,5-d]pyridazin-4(5H)-ones
  作者：Oya Ünsal-Tan、Kevser Özden、Arvi Rauk、Ayla Balkan

  DOI：10.1016/j.ejmech.2010.02.012

  日期：2010.6

  In this study, new isoxazolo[4,5-d]pyridazin-4(5H)-one derivatives having an N-acylhydrazone moiety were synthesized. The compounds were tested for their COX inhibitory activities using NS-398 and indomethacine as reference compounds. Although the compounds had an inhibitory profile against both COX-1 and COX-2, most were found to be more selective against COX-2 by a small percentage of inhibition, at the concentration of 50 mu M. Docking studies were clone to understand the interactions of the tested compounds with the active site of COX-2. It was observed that the compounds fit into, and interacted with, the hydrophobic parts which are common in the active pocket of COX-1 and COX-2 enzymes but could not fit to the area which is specific for COX-2 enzyme.