3-Methyl-6-pyrrolidin-1-yl-pyridazino[4,3-c]isoquinoline | 96825-97-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 英文名称: 3-Methyl-6-pyrrolidin-1-yl-pyridazino[4,3-c]isoquinoline
• 英文别名: Pyridazino(4,3-c)isoquinoline, 3-methyl-6-(1-pyrrolidinyl)-；3-methyl-6-pyrrolidin-1-ylpyridazino[4,3-c]isoquinoline
• CAS: 96825-97-7
• 化学式: C₁₆H₁₆N₄
• 分子量: 264.33
• InChiKey: YPWBXHJHCRFZQE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  41.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  3-Methyl-5H-pyridazino[4,3-c]isoquinolin-6-one 在 吡啶 、 五氯化磷 、 三氯氧磷 作用下， 以 乙二醇二甲醚 为溶剂， 反应 15.0h， 生成 3-Methyl-6-pyrrolidin-1-yl-pyridazino[4,3-c]isoquinoline
  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：——
• 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).