9,13-imino-8H-azocino[2,1-a]isoquinolin-8-one, 5,6,9,10,11,12,13,13a-octahydro-3-chloro- | 878561-00-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 四氢异喹啉
• 英文名称: 9,13-imino-8H-azocino[2,1-a]isoquinolin-8-one, 5,6,9,10,11,12,13,13a-octahydro-3-chloro-
• 英文别名: 6-chloro-11,17-diazatetracyclo[11.3.1.02,11.03,8]heptadeca-3(8),4,6-trien-12-one
• CAS: 878561-00-3
• 化学式: C₁₅H₁₇ClN₂O
• 分子量: 276.766
• InChiKey: ZYEBWNSXCQNAPS-UHFFFAOYSA-N

物化性质

• 沸点：
  469.2±45.0 °C(Predicted)
• 密度：
  1.34±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.29
• 重原子数：
  19.0
• 可旋转键数：
  0.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  32.34
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  9,13-imino-8H-azocino[2,1-a]isoquinolin-8-one, 5,6,9,10,11,12,13,13a-octahydro-3-chloro- 、 氧代(3,4,5-三甲氧基苯基)乙酸 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以64%的产率得到1-{6-Chloro-12-oxo-11,17-diazatetracyclo[11.3.1.0^{2,11}.0^{3,8}]heptadeca-3(8),4,6-trien-17-yl}-2-(3,4,5-trimethoxyphenyl)ethane-1,2-dione
  参考文献：
  名称：

  Design, Synthesis, and Biological Activity of Novel Polycyclic Aza-Amide FKBP12 Ligands

  摘要：

  Since the discovery that FK-506 promotes neurite outgrowth, considerable attention has been focused on the development of potent nonimmunosuppressive ligands for FK-506 binding proteins (FKBPs). Such neuroimmunophilin agents have been reported to show neuroregenerative activity in a variety of cell and animal models including neurite outgrowth, age-related cognitive decline, Parkinson's disease, peripheral nerve injury, optic nerve degeneration, and diabetic neuropathy. We have designed and synthesized a unique series of tetracyclic aza-amides that have been shown to be potent FKBP12 rotamase inhibitors. The structure-activity relationships established in this study have demonstrated diverse structural modifications that result in potent rotamase inhibitory activity.

  DOI：

  10.1021/jm049161u
• 作为产物：
  描述：

  2,4-Dioxo-3-oxa-9-aza-bicyclo[3.3.1]nonane-9-carboxylic acid benzyl ester 以 甲苯 为溶剂， 反应 17.5h， 生成 9,13-imino-8H-azocino[2,1-a]isoquinolin-8-one, 5,6,9,10,11,12,13,13a-octahydro-3-chloro-
  参考文献：
  名称：

  Design, Synthesis, and Biological Activity of Novel Polycyclic Aza-Amide FKBP12 Ligands

  摘要：

  Since the discovery that FK-506 promotes neurite outgrowth, considerable attention has been focused on the development of potent nonimmunosuppressive ligands for FK-506 binding proteins (FKBPs). Such neuroimmunophilin agents have been reported to show neuroregenerative activity in a variety of cell and animal models including neurite outgrowth, age-related cognitive decline, Parkinson's disease, peripheral nerve injury, optic nerve degeneration, and diabetic neuropathy. We have designed and synthesized a unique series of tetracyclic aza-amides that have been shown to be potent FKBP12 rotamase inhibitors. The structure-activity relationships established in this study have demonstrated diverse structural modifications that result in potent rotamase inhibitory activity.

  DOI：

  10.1021/jm049161u