12-amino-6H-7,8,10,11-tetrahydro-7,11-methanocyclooctano[b]quinolino-9-one | 151474-95-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 12-amino-6H-7,8,10,11-tetrahydro-7,11-methanocyclooctano[b]quinolino-9-one
• 英文别名: 3-amino-10-azatetracyclo[11.3.1.02,11.04,9]heptadeca-2,4,6,8,10-pentaen-15-one
• CAS: 151474-95-2
• 化学式: C₁₆H₁₆N₂O
• 分子量: 252.316
• InChiKey: KFBYFDGQEGSCDP-UHFFFAOYSA-N

物化性质

• 沸点：
  482.2±45.0 °C(Predicted)
• 密度：
  1.283±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.83
• 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：
  0.38
• 拓扑面积：
  55.98
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  12-amino-6H-7,8,10,11-tetrahydro-7,11-methanocyclooctano[b]quinolino-9-one 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 12.0h， 生成 rac-12-amino-6,7,8,9,10,11-hexahydro-7,11-methanocycloocta[b]quinoline-endo-9-ol
  参考文献：
  名称：

  Synthesis and evaluation of tacrine–Huperzine a hybrids as acetylcholinesterase inhibitors of potential interest for the treatment of alzheimer’s disease

  摘要：

  Seventeen polycyclic compounds related to tacrine and huperzine A have been prepared as racemic mixtures and tested as acetylcholinesterase (AChE) inhibitors. The conjunctive pharmacomodulation of huperzine A (carbobicyclic substructure) and tacrine (4-aminoquinoline substructure) led to compound 7jy, 2.5 times less active than tacrine as AChE inhibitor, but much more active than its (Z)-stereoisomer (7iy). Derivatives 7dy and 7ey, lacking the ethylidene substituent, showed to be more active than tacrine. Many other structural modifications of 7jy led to less active compounds. Compounds 7dy and 7ey also showed to be much more active than tacrine in reversing the partial neuromuscular blockade induced by d-tubocurarine. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(98)00015-7
• 作为产物：
  描述：

  7-(2-cyanophenylimino)bicyclo<3.3.1>nonan-3-one 在 zinc(II) chloride 作用下， 以 硝基苯 为溶剂， 反应 2.0h， 以62%的产率得到12-amino-6H-7,8,10,11-tetrahydro-7,11-methanocyclooctano[b]quinolino-9-one
  参考文献：
  名称：

  Synthesis and evaluation of tacrine-related compounds for the treatment of Alzheimer's disease

  摘要：

  A number of polycyclic compounds related to tacrine have been prepared by condensation of ortho-aminobenzonitriles and 2-aminocyclopentenecarbonitrile with several C2v-symmetric diketones under AlCl3 or ZnCl2 catalysis. Monocondensation products 8 together with syn- and anti-dicondensation products 9 and 10, respectively, were formed in different proportions depending mainly on the starting diketone. These compounds were separated by column chromatography, fully characterized by spectroscopic and elemental analyses and tested as acetylcholinesterase (AchE) inhibitors. Syn- and anti-compounds 9 and 10, derived from diketones 7y and 7z, have significant anti-AchE activity although compounds 8 and derivatives of diketones 7v, 7w and 7x were inactive in the range of concentrations studied. Compound 9ay was the mdst potent of the group, being 4.4-fold less active than tacrine as anti-AchE in biochemical assays, but only slightly less potent in biological studies and 3-fold less toxic. Compound 9ay was also able to reverse cognitive deficits in middle-aged rats.

  DOI：

  10.1016/0223-5234(94)90039-6