1-[(3-Phenyl-pyridazino[4,3-c]isoquinolin-6-yl)methylamino]-2-propanol | 96825-84-2

• 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: 1-[(3-Phenyl-pyridazino[4,3-c]isoquinolin-6-yl)methylamino]-2-propanol
• 英文别名: 1-(Methyl(3-phenylpyridazino(4,3-c)isoquinolin-6-yl)amino)-2-propanol；1-[methyl-(3-phenylpyridazino[4,3-c]isoquinolin-6-yl)amino]propan-2-ol
• CAS: 96825-84-2
• 化学式: C₂₁H₂₀N₄O
• 分子量: 344.416
• InChiKey: OKKPPAJEVLEIKD-UHFFFAOYSA-N

物化性质

• 沸点：
  570.1±60.0 °C(Predicted)
• 密度：
  1.268±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  62.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  3-phenyl-6H-<2>benzopyrano<4,3-c>pyridazin-6-one 在 乙酸铵 、 五氯化磷 、 三氯氧磷 作用下， 以 乙二醇二甲醚 为溶剂， 反应 20.5h， 生成 1-[(3-Phenyl-pyridazino[4,3-c]isoquinolin-6-yl)methylamino]-2-propanol
  参考文献：
  名称：

  Benzodiazepine receptor binding and anticonflict activity in a series of 3,6-disubstituted pyridazino[4,3-c]isoquinolines devoid of anticonvulsant properties

  摘要：

  A series of 3,6-disubstituted pyridazino[4,3-c]isoquinolines were synthesized and tested for their ability to inhibit the binding of [3H]diazepam to rat brain receptors in vitro. Compounds bearing a phenyl, 4-methoxyphenyl, or methyl group at position 3 and a dialkylamino group at position 6 showed the highest affinity in the binding assay and were subsequently evaluated for their anticonflict and anticonvulsant effects. All of these compounds (5a-1 and 5q) were active in the Vogel rat conflict procedure, but none prevented convulsions in mice induced either by metrazol or bicuculline. 3-Phenyl-6-pyrrolidinylpyridazino[4,3-c]isoquinoline (5d) with a Ki = 11.4 nM in the binding assay exhibited the best potency in the anticonflict assay (MED 5 mg/kg ip) and did not produce neuromuscular impairment at the highest dose tested (50 mg/kg ip).

  DOI：

  10.1021/jm00147a034

文献信息

• TOJA, E.;TARZIA, G.;BARONE, D.;LUZZANI, F.;GALLICO, L., J. MED. CHEM., 1981, 28, N 9, 1314-1319
  作者：TOJA, E.、TARZIA, G.、BARONE, D.、LUZZANI, F.、GALLICO, L.

  DOI：——

  日期：——
• Pyridazino(4,3-c)isoquinoline derivatives
  申请人：GRUPPO LEPETIT S.p.A.

  公开号：EP0134461B1

  公开（公告）日：1987-10-07
• US4716159A
  申请人：——

  公开号：US4716159A

  公开（公告）日：1987-12-29
• Benzodiazepine receptor binding and anticonflict activity in a series of 3,6-disubstituted pyridazino[4,3-c]isoquinolines devoid of anticonvulsant properties
  作者：Emilio Toja、Giorgio Tarzia、Domenico Barone、Franco Luzzani、Licia Gallico

  DOI：10.1021/jm00147a034

  日期：1985.9

  A series of 3,6-disubstituted pyridazino[4,3-c]isoquinolines were synthesized and tested for their ability to inhibit the binding of [3H]diazepam to rat brain receptors in vitro. Compounds bearing a phenyl, 4-methoxyphenyl, or methyl group at position 3 and a dialkylamino group at position 6 showed the highest affinity in the binding assay and were subsequently evaluated for their anticonflict and anticonvulsant effects. All of these compounds (5a-1 and 5q) were active in the Vogel rat conflict procedure, but none prevented convulsions in mice induced either by metrazol or bicuculline. 3-Phenyl-6-pyrrolidinylpyridazino[4,3-c]isoquinoline (5d) with a Ki = 11.4 nM in the binding assay exhibited the best potency in the anticonflict assay (MED 5 mg/kg ip) and did not produce neuromuscular impairment at the highest dose tested (50 mg/kg ip).