1-aminobenzobicyclo[2.2.2]octene | 201275-20-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: 1-aminobenzobicyclo[2.2.2]octene
• 英文别名: Tricyclo[6.2.2.02,7]dodeca-2,4,6-trien-1-amine
• CAS: 201275-20-9
• 化学式: C₁₂H₁₅N
• 分子量: 173.258
• InChiKey: JSESCJMMLGFKST-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.5
• 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：

  1,5-二溴戊烷 、 1-aminobenzobicyclo[2.2.2]octene 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.75h， 生成 1-Tricyclo[6.2.2.0^2,7]dodeca-2(7),3,5-trien-1-yl-piperidine
  参考文献：
  名称：

  Rigid Phencyclidine Analogues. Binding to the Phencyclidine and σ₁ Receptors

  摘要：

  Three phencyclidine (PCP) analogues possessing a highly rigid carbocyclic structure and an attached piperidine ring which is free to rotate were synthesized. Each analogue has a specific fixed orientation of the ammonium center of the piperidinium ring to the centrum of the phenyl ring. The binding affinities of the rigid analogues 1-piperidino-7,8-benzobicyclo[4.2.0]octene (14), 1-piperidinobenzobicyclo[2.2.1]heptene (16), and 1-piperidinobenzobicyclo[2.2.2]octene (13) for the PCP receptor ([H-3]TCP) and sigma-receptor (NANM) were determined. The three analogues show low to no affinity for the PCP receptor but good affinity for the sigma-receptor and can be considered sigma-receptor selective ligands with PCP/sigma ratios of 13, 293, and 368, respectively. The binding affinities for the sigma-receptor are rationalized in terms of a model for the sigma-pharmacophore.

  DOI：

  10.1021/jm970059p
• 作为产物：
  描述：

  methyl cyclohexa-1,3-diene-1-carboxylate 在 palladium on activated charcoal 氢氧化钾 、 五氯化磷 、 羟基甲苯磺酰碘苯 、 氨 、 氢气 、 亚硝酸异戊酯 作用下， 以 甲醇 、 二氯甲烷 、 乙腈 为溶剂， -78.0~70.0 ℃ 、206.84 kPa 条件下， 反应 51.0h， 生成 1-aminobenzobicyclo[2.2.2]octene
  参考文献：
  名称：

  Rigid Phencyclidine Analogues. Binding to the Phencyclidine and σ₁ Receptors

  摘要：

  Three phencyclidine (PCP) analogues possessing a highly rigid carbocyclic structure and an attached piperidine ring which is free to rotate were synthesized. Each analogue has a specific fixed orientation of the ammonium center of the piperidinium ring to the centrum of the phenyl ring. The binding affinities of the rigid analogues 1-piperidino-7,8-benzobicyclo[4.2.0]octene (14), 1-piperidinobenzobicyclo[2.2.1]heptene (16), and 1-piperidinobenzobicyclo[2.2.2]octene (13) for the PCP receptor ([H-3]TCP) and sigma-receptor (NANM) were determined. The three analogues show low to no affinity for the PCP receptor but good affinity for the sigma-receptor and can be considered sigma-receptor selective ligands with PCP/sigma ratios of 13, 293, and 368, respectively. The binding affinities for the sigma-receptor are rationalized in terms of a model for the sigma-pharmacophore.

  DOI：

  10.1021/jm970059p

文献信息

• Substituted pyrrolo[1,2-a]pyrimidines and their use in the treatment of medical disorders
  申请人：Lysosomal Therapeutics Inc.

  公开号：US10751341B2

  公开（公告）日：2020-08-25

  The invention provides substituted pyrrolo[1,2-a]pyrimidines and related organic compounds, compositions containing such compounds, medical kits, and methods for using such compounds and compositions to treat medical disorders, e.g., Gaucher disease, Parkinson's disease, Lewy body disease, dementia, or multiple system atrophy, in a patient. Exemplary substituted pyrrolo[1,2-a]pyrimidines compounds described herein include substituted 2,4-dimethyl-N-phenylpyrrolo[1,2-a]pyrimidine-8-carboxamide compounds and variants thereof.

  本发明提供了取代的吡咯并[1,2-a]嘧啶及相关有机化合物、含有此类化合物的组合物、医用试剂盒以及使用此类化合物和组合物治疗患者的内科疾病（如戈谢病、帕金森病、路易体病、痴呆症或多系统萎缩）的方法。本文所述的示例性取代吡咯并[1,2-a]嘧啶化合物包括取代的2,4-二甲基-N-苯基吡咯并[1,2-a]嘧啶-8-甲酰胺化合物及其变体。
• SUBSTITUTED PYRROLO[1,2-A]PYRIMIDINES AND THEIR USE IN THE TREATMENT OF MEDICAL DISORDERS
  申请人：Lysosomal Therapeutics Inc.

  公开号：EP3215509B1

  公开（公告）日：2020-02-26
• Rigid Phencyclidine Analogues. Binding to the Phencyclidine and σ₁ Receptors
  作者：Robert M. Moriarty、Livia A. Enache、Lei Zhao、Richard Gilardi、Mariena V. Mattson、Om Prakash

  DOI：10.1021/jm970059p

  日期：1998.2.1

  Three phencyclidine (PCP) analogues possessing a highly rigid carbocyclic structure and an attached piperidine ring which is free to rotate were synthesized. Each analogue has a specific fixed orientation of the ammonium center of the piperidinium ring to the centrum of the phenyl ring. The binding affinities of the rigid analogues 1-piperidino-7,8-benzobicyclo[4.2.0]octene (14), 1-piperidinobenzobicyclo[2.2.1]heptene (16), and 1-piperidinobenzobicyclo[2.2.2]octene (13) for the PCP receptor ([H-3]TCP) and sigma-receptor (NANM) were determined. The three analogues show low to no affinity for the PCP receptor but good affinity for the sigma-receptor and can be considered sigma-receptor selective ligands with PCP/sigma ratios of 13, 293, and 368, respectively. The binding affinities for the sigma-receptor are rationalized in terms of a model for the sigma-pharmacophore.