2-(1,3-Benzodioxol-5-yl)-6-ethoxyimidazo[1,2-b]pyridazine | 184015-11-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 英文名称: 2-(1,3-Benzodioxol-5-yl)-6-ethoxyimidazo[1,2-b]pyridazine
• CAS: 184015-11-0
• 化学式: C₁₅H₁₃N₃O₃
• 分子量: 283.287
• InChiKey: CAVZUSHRVLTZPZ-UHFFFAOYSA-N

物化性质

• 密度：
  1.42±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  57.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-fluoro-N-(hydroxymethyl)benzamide 、 2-(1,3-Benzodioxol-5-yl)-6-ethoxyimidazo[1,2-b]pyridazine 在 硫酸 、 溶剂黄146 作用下， 反应 24.0h， 以19%的产率得到N-[[2-(1,3-benzodioxol-5-yl)-6-ethoxyimidazo[1,2-b]pyridazin-3-yl]methyl]-2-fluorobenzamide
  参考文献：
  名称：

  Syntheses, pharmacological evaluation and molecular modelling of substituted 6-alkoxyimidazo[1,2-b]pyridazines as new ligands for the benzodiazepine receptor

  摘要：

  A series of 2,3-disubstituted-6-alkoxyimidazo[1,2-b] has been synthesized and evaluated for in vitro affinity for the benzodiazepine receptor (BZR). 3-(Benzamidomethyl or substituted benzamidomethyl)-6-methoxy-2-(3,4-methylenedioxyphenyl)imidazo[1,2-b]pyridazines were found to be the most potent BZR ligands (eg, 4a, IC50 7 nM; 4e, IC50 14 nM; 4v, IC50 8 nM). Imidazo[1,2-b]pyridazines unsubstituted in the 3-position, or containing builder alkoxy groups in the 6-position, were found to bind less strongly to the BZR. Selected compounds from the series were identified from in vitro GABA-shift experiments as BZR agonists. Molecular modelling has been employed to identify the common pharmacophoric points of lipophilic and hydrogen bonding, ligand-receptor interaction and areas of steric hindrance for these substituted imidazo[1,2-b]pyridazines at the BZR.

  DOI：

  10.1016/0223-5234(96)85873-9
• 作为产物：
  描述：

  1-(1,3-苯并氧)2-溴乙酮 、 6-乙氧基吡嗪-3-胺 在 碳酸氢钠 作用下， 生成 2-(1,3-Benzodioxol-5-yl)-6-ethoxyimidazo[1,2-b]pyridazine
  参考文献：
  名称：

  Syntheses, pharmacological evaluation and molecular modelling of substituted 6-alkoxyimidazo[1,2-b]pyridazines as new ligands for the benzodiazepine receptor

  摘要：

  A series of 2,3-disubstituted-6-alkoxyimidazo[1,2-b] has been synthesized and evaluated for in vitro affinity for the benzodiazepine receptor (BZR). 3-(Benzamidomethyl or substituted benzamidomethyl)-6-methoxy-2-(3,4-methylenedioxyphenyl)imidazo[1,2-b]pyridazines were found to be the most potent BZR ligands (eg, 4a, IC50 7 nM; 4e, IC50 14 nM; 4v, IC50 8 nM). Imidazo[1,2-b]pyridazines unsubstituted in the 3-position, or containing builder alkoxy groups in the 6-position, were found to bind less strongly to the BZR. Selected compounds from the series were identified from in vitro GABA-shift experiments as BZR agonists. Molecular modelling has been employed to identify the common pharmacophoric points of lipophilic and hydrogen bonding, ligand-receptor interaction and areas of steric hindrance for these substituted imidazo[1,2-b]pyridazines at the BZR.

  DOI：

  10.1016/0223-5234(96)85873-9

文献信息

• Syntheses, pharmacological evaluation and molecular modelling of substituted 6-alkoxyimidazo[1,2-b]pyridazines as new ligands for the benzodiazepine receptor
  作者：PW Harrison、GB Barlin、LP Davies、SJ Ireland、P Mátyus、MG Wong

  DOI：10.1016/0223-5234(96)85873-9

  日期：1996.1

  A series of 2,3-disubstituted-6-alkoxyimidazo[1,2-b] has been synthesized and evaluated for in vitro affinity for the benzodiazepine receptor (BZR). 3-(Benzamidomethyl or substituted benzamidomethyl)-6-methoxy-2-(3,4-methylenedioxyphenyl)imidazo[1,2-b]pyridazines were found to be the most potent BZR ligands (eg, 4a, IC50 7 nM; 4e, IC50 14 nM; 4v, IC50 8 nM). Imidazo[1,2-b]pyridazines unsubstituted in the 3-position, or containing builder alkoxy groups in the 6-position, were found to bind less strongly to the BZR. Selected compounds from the series were identified from in vitro GABA-shift experiments as BZR agonists. Molecular modelling has been employed to identify the common pharmacophoric points of lipophilic and hydrogen bonding, ligand-receptor interaction and areas of steric hindrance for these substituted imidazo[1,2-b]pyridazines at the BZR.