ethyl 4-(6-iminopyridazin-1-yl)butanoate | 1402146-94-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: ethyl 4-(6-iminopyridazin-1-yl)butanoate
• CAS: 1402146-94-4
• 化学式: C₁₀H₁₅N₃O₂
• 分子量: 209.248
• InChiKey: XVJDATYNGVWNCM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.71
• 重原子数：
  15.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  67.97
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  ethyl 4-(6-iminopyridazin-1-yl)butanoate 在 盐酸 、 溶剂黄146 作用下， 以 水 为溶剂， 反应 12.0h， 以8%的产率得到4-(6-iminopyridazin-1-yl)butanoic acid hydrochloride
  参考文献：
  名称：

  Competitive antagonism of insect GABA receptors by iminopyridazine derivatives of GABA

  摘要：

  A series of 4-(6-imino-3-aryl/heteroarylpyridazin-1-yl) butanoic acids were synthesized and examined for antagonism of GABA receptors from three insect species. When tested against small brown planthopper GABA receptors, the 3,4-methylenedioxyphenyl and the 2-naphthyl analogues showed complete inhibition of GABA-induced fluorescence changes at 100 mu M in assays using a membrane potential probe. Against common cutworm GABA receptors, these analogues displayed approximately 86% and complete inhibition of GABA-induced fluorescence changes at 100 mu M, respectively. The 4-biphenyl and 4-phenoxyphenyl analogues showed moderate inhibition at 10 mu M in these receptors, although the inhibition at 100 mu M was not complete. Against American cockroach GABA receptors, the 4-biphenyl analogue exhibited the greatest inhibition (approximately 92%) of GABA-induced currents, when tested at 500 mu M using a patch-clamp technique. The second most active analogue was the 2-naphthyl analogue with approximately 85% inhibition. The 3-thienyl analogue demonstrated competitive inhibition of cockroach GABA receptors. Homology modeling and ligand docking studies predicted that hydrophobic 3-substituents could interact with an accessory binding site at the orthosteric binding site. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.07.049
• 作为产物：
  描述：

  哒嗪-3-胺 、 4-溴丁酸乙酯 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 、 水 为溶剂， 生成 ethyl 4-(6-iminopyridazin-1-yl)butanoate
  参考文献：
  名称：

  Competitive antagonism of insect GABA receptors by iminopyridazine derivatives of GABA

  摘要：

  A series of 4-(6-imino-3-aryl/heteroarylpyridazin-1-yl) butanoic acids were synthesized and examined for antagonism of GABA receptors from three insect species. When tested against small brown planthopper GABA receptors, the 3,4-methylenedioxyphenyl and the 2-naphthyl analogues showed complete inhibition of GABA-induced fluorescence changes at 100 mu M in assays using a membrane potential probe. Against common cutworm GABA receptors, these analogues displayed approximately 86% and complete inhibition of GABA-induced fluorescence changes at 100 mu M, respectively. The 4-biphenyl and 4-phenoxyphenyl analogues showed moderate inhibition at 10 mu M in these receptors, although the inhibition at 100 mu M was not complete. Against American cockroach GABA receptors, the 4-biphenyl analogue exhibited the greatest inhibition (approximately 92%) of GABA-induced currents, when tested at 500 mu M using a patch-clamp technique. The second most active analogue was the 2-naphthyl analogue with approximately 85% inhibition. The 3-thienyl analogue demonstrated competitive inhibition of cockroach GABA receptors. Homology modeling and ligand docking studies predicted that hydrophobic 3-substituents could interact with an accessory binding site at the orthosteric binding site. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.07.049