11-(3-Imino-5,6-dihydro-3H-benzo[h]cinnolin-2-yl)-undecanoic acid ethyl ester | 702683-15-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 11-(3-Imino-5,6-dihydro-3H-benzo[h]cinnolin-2-yl)-undecanoic acid ethyl ester
• CAS: 702683-15-6
• 化学式: C₂₅H₃₅N₃O₂
• 分子量: 409.572
• InChiKey: WFPWRHDOVMFPRZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  30.0
• 可旋转键数：
  12.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.56
• 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：

  11-(3-Imino-5,6-dihydro-3H-benzo[h]cinnolin-2-yl)-undecanoic acid ethyl ester 在 N-甲基吡咯烷酮 、 盐酸 、 1-羟基苯并三唑 、 溶剂黄146 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 31.0h， 生成 MW01-026Z
  参考文献：
  名称：

  An aminopyridazine-based inhibitor of a pro-apoptotic protein kinase attenuates hypoxia-ischemia induced acute brain injury

  摘要：

  Death associated protein kinase (DAPK) is a calcium and calmodulin regulated enzyme that functions early in eukaryotic programmed cell death, or apoptosis. To validate DAPK as a potential drug discovery target for acute brain injury, the first small molecule DAPK inhibitor was synthesized and tested in vivo. A single injection of the aminopyridazine-based inhibitor administered 6 h after injury attenuated brain tissue or neuronal biomarker loss measured, respectively, 1 week and 3 days later. Because aminopyridazine is a privileged structure in neuropharmacology, we determined the high-resolution crystal structure of a binary complex between the kinase domain and a molecular fragment of the DAPK inhibitor. The co-crystal structure describes a structural basis for interaction and provides a firm foundation for structure-assisted design of lead compounds with appropriate molecular properties for future drug development.

  DOI：

  10.1016/s0960-894x(03)00733-9
• 作为产物：
  描述：

  3-氯-5,6-二氢-苯并[h]噌啉 在 镍 氢气 、 一水合肼 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 生成 11-(3-Imino-5,6-dihydro-3H-benzo[h]cinnolin-2-yl)-undecanoic acid ethyl ester
  参考文献：
  名称：

  Discovery of a 3-Amino-6-phenyl-pyridazine Derivative as a New Synthetic Antineuroinflammatory Compound

  摘要：

  Excessive glial activation, with overproduction of cytokines and oxidative stress products, is detrimental and a hallmark of neurodegenerative disease pathology. Suppression of glial activation is a potential therapeutic approach, and protein kinases are targets of some antiinflammatory drugs. To address an unmet need for selective inhibitors of glial activation, we developed a novel 3-amino-6-phenylpyridazine derivative that selectively blocks increased IL-1beta, iNOS, and NO production by activated glia, without inhibition of potentially beneficial glial functions.

  DOI：

  10.1021/jm015573g