3-[2-(3-chloro-phenyl)ethyl]-2,4-dioxo-3,9-diaza-bicyclo[3.3.1]nonane-9-carboxylic acid benzyl ester | 878560-75-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-[2-(3-chloro-phenyl)ethyl]-2,4-dioxo-3,9-diaza-bicyclo[3.3.1]nonane-9-carboxylic acid benzyl ester
• 英文别名: benzyl 3-[2-(3-chlorophenyl)ethyl]-2,4-dioxo-3,9-diazabicyclo[3.3.1]nonane-9-carboxylate
• CAS: 878560-75-9
• 化学式: C₂₃H₂₃ClN₂O₄
• 分子量: 426.9
• InChiKey: UAMPHIHSGOOCIT-UHFFFAOYSA-N

物化性质

• 沸点：
  620.8±55.0 °C(Predicted)
• 密度：
  1.316±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.81
• 重原子数：
  30.0
• 可旋转键数：
  5.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  66.92
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  3-[2-(3-chloro-phenyl)ethyl]-2,4-dioxo-3,9-diaza-bicyclo[3.3.1]nonane-9-carboxylic acid benzyl ester 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， 生成 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：

  吡啶-2,6-二甲酸 在 rhodium on aluminium sodium hydroxide 、 氢气 、 乙酸酐 作用下， 以 甲苯 为溶剂， 20.0~65.0 ℃ 、344.74 kPa 条件下， 反应 18.0h， 生成 3-[2-(3-chloro-phenyl)ethyl]-2,4-dioxo-3,9-diaza-bicyclo[3.3.1]nonane-9-carboxylic acid benzyl ester
  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