8-hydroxy-6-(3-oxobutyl)-pyrido[2,3-d]pyridazin-5(6H)-one | 18691-63-9

• 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: 8-hydroxy-6-(3-oxobutyl)-pyrido[2,3-d]pyridazin-5(6H)-one
• 英文别名: 6-(3-oxobutyl)-7H-pyrido[2,3-d]pyridazine-5,8-dione
• CAS: 18691-63-9
• 化学式: C₁₁H₁₁N₃O₃
• 分子量: 233.227
• InChiKey: KZUOBWINOWVDGG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  79.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 8-hydroxy-6-(3-oxobutyl)-pyrido[2,3-d]pyridazin-5(6H)-one 在 吡啶 作用下， 以100%的产率得到8-acetoxy-6-(3-oxobutyl)-pyrido[2,3-d]pyridazin-5(6H)-one
  参考文献：
  名称：

  Synthesis and Structure Investigations of Potential Sedative and Anticonvulsant Hydroxy- and Acetoxy-N-(3-oxobutyl)-pyrido[2,3-d]pyridazinones a

  摘要：

  Novel N-(3-oxobutyl)-hydroxy- and acetoxypyrido[2,3-d]pyridazinones were synthesized and tested in vivo for their sedative and anticonvulsant activity. The Michael-type reaction of quinolinic acid hydrazide and methyl vinyl ketone afforded a mixture of two isomers, 5-hydroxy-N--(7)(3-oxobutyl)pyrido[2,3-d]pyridazin-8(7H)-one and 8-hydroxy-N-6-(3-oxobutyl)-pyrido[2,3,-d]pyridazin-5-(6H)one, in a ratio of 2:1 which were separated by crystallization. Subsequent acetylation of both isomers yielded the corresponding 5- and 8-acetoxy compounds. The structures of the compounds were proven and completely assigned on the basis of H-1, C-13, N-15 NMR, and 1D NOE difference spectra as well as 2D C,H-correlation experiments. Preliminary pharmacological tests showed low acute toxicity with a LD50 > 1000 mg/kg in the mouse and sedative activity for the title compounds. 5-Acetoxy-N-7(3-oxobutyl)-pyrido[2,3-d]pyridazin-8(7H)-one displayed a borderline anticonvulsant activity in the metrazole test model.

  DOI：

  10.1007/s00706-002-0473-z
• 作为产物：
  描述：

  吡啶并[2,3-d]吡嗪-5,8-二醇 、 丁烯酮 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 4.0h， 以42.9%的产率得到5-hydroxy-7-(3-oxobutyl)-pyrido[2,3-d]pyridazin-8(7H)-one
  参考文献：
  名称：

  Synthesis and Structure Investigations of Potential Sedative and Anticonvulsant Hydroxy- and Acetoxy-N-(3-oxobutyl)-pyrido[2,3-d]pyridazinones a

  摘要：

  Novel N-(3-oxobutyl)-hydroxy- and acetoxypyrido[2,3-d]pyridazinones were synthesized and tested in vivo for their sedative and anticonvulsant activity. The Michael-type reaction of quinolinic acid hydrazide and methyl vinyl ketone afforded a mixture of two isomers, 5-hydroxy-N--(7)(3-oxobutyl)pyrido[2,3-d]pyridazin-8(7H)-one and 8-hydroxy-N-6-(3-oxobutyl)-pyrido[2,3,-d]pyridazin-5-(6H)one, in a ratio of 2:1 which were separated by crystallization. Subsequent acetylation of both isomers yielded the corresponding 5- and 8-acetoxy compounds. The structures of the compounds were proven and completely assigned on the basis of H-1, C-13, N-15 NMR, and 1D NOE difference spectra as well as 2D C,H-correlation experiments. Preliminary pharmacological tests showed low acute toxicity with a LD50 > 1000 mg/kg in the mouse and sedative activity for the title compounds. 5-Acetoxy-N-7(3-oxobutyl)-pyrido[2,3-d]pyridazin-8(7H)-one displayed a borderline anticonvulsant activity in the metrazole test model.

  DOI：

  10.1007/s00706-002-0473-z

文献信息

• Synthesis and Structure Investigations of Potential Sedative and Anticonvulsant Hydroxy- and Acetoxy-N-(3-oxobutyl)-pyrido[2,3-d]pyridazinones a
  作者：Edith Gößnitzer、Ales Krbavcic、Winfried Wendelin、Marija Krbavcic

  DOI：10.1007/s00706-002-0473-z

  日期：2002.9.1

  Novel N-(3-oxobutyl)-hydroxy- and acetoxypyrido[2,3-d]pyridazinones were synthesized and tested in vivo for their sedative and anticonvulsant activity. The Michael-type reaction of quinolinic acid hydrazide and methyl vinyl ketone afforded a mixture of two isomers, 5-hydroxy-N--(7)(3-oxobutyl)pyrido[2,3-d]pyridazin-8(7H)-one and 8-hydroxy-N-6-(3-oxobutyl)-pyrido[2,3,-d]pyridazin-5-(6H)one, in a ratio of 2:1 which were separated by crystallization. Subsequent acetylation of both isomers yielded the corresponding 5- and 8-acetoxy compounds. The structures of the compounds were proven and completely assigned on the basis of H-1, C-13, N-15 NMR, and 1D NOE difference spectra as well as 2D C,H-correlation experiments. Preliminary pharmacological tests showed low acute toxicity with a LD50 > 1000 mg/kg in the mouse and sedative activity for the title compounds. 5-Acetoxy-N-7(3-oxobutyl)-pyrido[2,3-d]pyridazin-8(7H)-one displayed a borderline anticonvulsant activity in the metrazole test model.