古巴-1-基甲胺 | 150234-60-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 中文名称: 古巴-1-基甲胺
• 英文名称: (aminomethyl)cubane
• 英文别名: pentacyclo[4.2.0.0^2,5.0^3,8.0^4,7]octane-1-methanamine；cubanylmethylamine；(cuban-1-yl)methylamine；1-cubanemethylamine；Cuban-1-ylmethanamine
• CAS: 150234-60-9
• 化学式: C₉H₁₁N
• mdl: MFCD19204783
• 分子量: 133.193
• InChiKey: CRHYPLCALPANOH-UHFFFAOYSA-N

物化性质

• 沸点：
  188.8±8.0 °C(Predicted)
• 密度：
  1.557±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  26
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  古巴-1-基甲胺 在 Tris-HCl buffer 作用下， 以 水 为溶剂， 生成 cubanecarboxaldehyde
  参考文献：
  名称：

  Inactivation of monoamine oxidase by (aminomethyl)cubane. First evidence for an .alpha.-amino radical during enzyme catalysis

  摘要：

  DOI：

  10.1021/ja00072a048
• 作为产物：
  描述：

  1-立方烷羧酸 在 lithium aluminium tetrahydride 、 草酰氯 、 氨 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 15.66h， 生成 古巴-1-基甲胺
  参考文献：
  名称：

  4-取代的古柏碳烯基胺：一类新的基于机理的单胺氧化酶B灭活剂。

  摘要：

  合成了苄基羰基胺（1a），（4-环丙基cubyl）羰基胺（1b）和（4-苯基cubyl）羰基胺（1c），它们是时间依赖性的单胺氧化酶B（MAO B）不可逆的灭活剂。底物可保护酶免于灭活，但β-巯基乙醇则不能，表明这些化合物是基于机理的灭活剂。所有这三种化合物也是MAO B的底物，分配比范围为152至536。4-取代的类似物比未取代的类似物更有效的灭活剂，表明在这类灭活剂中有利于4-取代。

  DOI：

  10.1021/jm9606249

文献信息

• Cubyl amides: Novel P2X7 receptor antagonists
  作者：Hendra Gunosewoyo、Jun Liu Guo、Maxwell R. Bennett、Mark J. Coster、Michael Kassiou

  DOI：10.1016/j.bmcl.2008.05.062

  日期：2008.7

  Polycyclic amides 2 and 5-9 were successfully synthesised and their lipophilicity profiles were evaluated using reverse-phase HPLC. All synthesised compounds possessed P2X7R antagonistic properties when tested on rat spinal cord microglia cells. Extensive screening for binding to other neuroreceptor subtypes demonstrated their P2X7 selectivity.

  成功合成了多环酰胺2和5-9，并使用反相HPLC评估了它们的亲脂性。当在大鼠脊髓小胶质细胞上进行测试时，所有合成的化合物均具有P2X7R拮抗特性。与其他神经受体亚型结合的广泛筛选证明了其对P2X7的选择性。
• The role of polycyclic frameworks in modulating P2X7 receptor function
  作者：Timothy B. Callis、Tristan A. Reekie、James O'Brien-Brown、Erick C.N. Wong、Eryn L. Werry、Nabiha Elias、William T. Jorgensen、John Tsanaktsidis、Louis M. Rendina、Michael Kassiou

  DOI：10.1016/j.tet.2017.10.075

  日期：2018.3

  Herein we describe our recent attempts to target the P2X7 receptor for potential treatment of neurological disorders. This work focusses on different polycycles including carborane, adamantane or cubane, joined by either a cyanoguanidine or an amide linker to phenyl or isoquinoline moieties. We have demonstrated the superiority of the adamantyl moiety over other polycycles in terms of synthetic accessibility and biological (cellular) activity. We have also shown that an amide or cyanoguanidine linker can greatly alter the biological activity of compounds. This SAR study provides important insights into the types of functionality required to target the P2X7 receptor. (C) 2017 Elsevier Ltd. All rights reserved.
• The First CNS-Active Carborane: A Novel P2X₇ Receptor Antagonist with Antidepressant Activity
  作者：Shane M. Wilkinson、Hendra Gunosewoyo、Melissa L. Barron、Aurelie Boucher、Michelle McDonnell、Peter Turner、Daniel E. Morrison、Maxwell R. Bennett、Iain S. McGregor、Louis M. Rendina、Michael Kassiou

  DOI：10.1021/cn500054n

  日期：2014.5.21

  Relative to other polycyclic frameworks (1-3), a carborane cage (4 and Cs center dot 5) exerts a significant biological effect as an inhibitor of the purinergic P2X(7) receptor (P2X(7)R) which allows one to target depression in vivo and thus demonstrate, for the first time, that a carborane has the capacity to modify CNS activity.[GRAPHICS]
• Structure–activity relationships of N-substituted 4-(trifluoromethoxy)benzamidines with affinity for GluN2B-containing NMDA receptors
  作者：Corinne Beinat、Samuel D. Banister、Jane Hoban、John Tsanaktsidis、Athanasios Metaxas、Albert D. Windhorst、Michael Kassiou

  DOI：10.1016/j.bmcl.2013.12.087

  日期：2014.2

  GluN2B subtype-selective NMDA antagonists represent promising therapeutic targets for the symptomatic treatment of multiple CNS pathologies. A series of N-benzyl substituted benzamidines were synthesised and the benzyl ring was further replaced with various polycyclic moieties. Compounds were evaluated for activity at GluN2B containing NMDA receptors where analogues 9, 12, 16 and 18 were the most potent of the series, replacement of the benzyl ring with polycycles resulted in a complete loss of activity. (C) 2013 Elsevier Ltd. All rights reserved.
• WO2008/64432
  申请人：——

  公开号：——

  公开（公告）日：——