6,7,8,15-tetrahydro-7,15-methanocyclooctano<1,2-b:5,4-b'>diquinoline-14,16-diamine | 151474-78-1

• 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: 6,7,8,15-tetrahydro-7,15-methanocyclooctano<1,2-b:5,4-b'>diquinoline-14,16-diamine
• 英文别名: 7,15-Methanocycloocta(1,2-b':5,4-b')diquinoline-14,16-diamine, 6,7,8,15-tetrahydro-；10,16-diazahexacyclo[11.11.1.02,11.04,9.015,24.017,22]pentacosa-2,4,6,8,10,15,17,19,21,23-decaene-3,23-diamine
• CAS: 151474-78-1
• 化学式: C₂₃H₂₀N₄
• 分子量: 352.439
• InChiKey: GSFHPTWMTXDOTC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  27
• 可旋转键数：
  0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  77.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  二环[3.3.1]壬-3,7-二酮 、 2-氨基苯甲腈 在 三氯化铝 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 3.0h， 以11%的产率得到6,7,8,15-tetrahydro-7,15-methanocyclooctano<1,2-b:5,4-b'>diquinoline-14,16-diamine
  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

文献信息

• Synthesis and evaluation of tacrine-related compounds for the treatment of Alzheimer's disease
  作者：F Aguado、A Badía、JE Baños、F Bosch、C Bozzo、P Camps、J Contreras、M Dierssen、C Escolano、DM Görbig、D Muñoz-Torrero、MD Pujol、M Simón、MT Vázquez、NM Vivas

  DOI：10.1016/0223-5234(94)90039-6

  日期：1994.1

  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.