6-Methoxy-11,17-diazatetracyclo[11.3.1.02,11.03,8]heptadeca-3(8),4,6-trien-12-one | 475301-75-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: 6-Methoxy-11,17-diazatetracyclo[11.3.1.02,11.03,8]heptadeca-3(8),4,6-trien-12-one
• CAS: 475301-75-8
• 化学式: C₁₆H₂₀N₂O₂
• 分子量: 272.347
• InChiKey: DVRAARRJIKKTFP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  41.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-Methoxy-11,17-diazatetracyclo[11.3.1.02,11.03,8]heptadeca-3(8),4,6-trien-12-one 、 3,4-二氟苯胺 在 氯磺酸 、 三乙胺 、 3,5-二甲基吡啶 作用下， 以 二氯甲烷 为溶剂， 生成 N-(3,4-difluorophenyl)-6-methoxy-12-oxo-11,17-diazatetracyclo[11.3.1.0^{2,11}.0^{3,8}]heptadeca-3(8),4,6-triene-17-sulfonamide
  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 6-Methoxy-11,17-diazatetracyclo[11.3.1.02,11.03,8]heptadeca-3(8),4,6-trien-12-one
  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