4-(2H-1,2,3-triazol-4-yl)-1-azabicyclo<2.2.1>heptane | 133366-36-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 三唑并吡啶类
• 英文名称: 4-(2H-1,2,3-triazol-4-yl)-1-azabicyclo<2.2.1>heptane
• 英文别名: 4-(2H-1,2,3-Triazol-4-yl)-1-azabicyclo[2.2.1]heptane；4-(2H-triazol-4-yl)-1-azabicyclo[2.2.1]heptane
• CAS: 133366-36-6
• 化学式: C₈H₁₂N₄
• 分子量: 164.21
• InChiKey: JIPXIMFIPDBGDM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  44.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  重氮甲烷 、 4-(2H-1,2,3-triazol-4-yl)-1-azabicyclo<2.2.1>heptane 以 乙醚 、 乙醇 为溶剂， 反应 4.0h， 以35%的产率得到4-(2-methyl-1,2,3-triazol-4-yl)-1-azabicyclo[2.2.1]-heptane
  参考文献：
  名称：

  Substituent variation in azabicyclic triazole- and tetrazole-based muscarinic receptor ligands

  摘要：

  The effect of variation of the 1-azabicyclic substituent on the novel 1,2,3-triazol-4-yl-, 1,2,4-triazol-1-yl-, tetrazol-5-yl-, and tetrazol-2-yl-based muscarinic receptor ligands ha, been studied, and the exo-azabicyclic[2.2.1]hept-3-yl substituent was found to give the most potent and efficacious compounds. In addition, variation of the second substituent on 1,2,4-triazol-1-yl- and tetrazol-2-yl-based muscarinic receptor ligands has yielded a series of novel compounds with high potencies and efficacies, ranging from full agonists to antagonists. Small lipophilic electron withdrawing substituents give potent but low efficacy compounds, while small polar electron donating substituents give potent and efficacious compounds. The activity of these compounds is described in terms of a model of the receptor involving lipophilic and hydrogen bonding interactions. These compounds provide muscarinic ligands with high potency and a range of efficacies suitable for testing as candidate drugs in the treatment of Alzheimer's disease.

  DOI：

  10.1021/jm00091a007
• 作为产物：
  描述：

  1-(1-氮杂双环[2.2.1]庚-4-基)-2-氯乙酮 在 甲醇 、 3-硝基苯甲酰基叠氮化物 、 氨 作用下， 以 乙腈 为溶剂， 反应 17.0h， 生成 4-(2H-1,2,3-triazol-4-yl)-1-azabicyclo<2.2.1>heptane
  参考文献：
  名称：

  Substituent variation in azabicyclic triazole- and tetrazole-based muscarinic receptor ligands

  摘要：

  The effect of variation of the 1-azabicyclic substituent on the novel 1,2,3-triazol-4-yl-, 1,2,4-triazol-1-yl-, tetrazol-5-yl-, and tetrazol-2-yl-based muscarinic receptor ligands ha, been studied, and the exo-azabicyclic[2.2.1]hept-3-yl substituent was found to give the most potent and efficacious compounds. In addition, variation of the second substituent on 1,2,4-triazol-1-yl- and tetrazol-2-yl-based muscarinic receptor ligands has yielded a series of novel compounds with high potencies and efficacies, ranging from full agonists to antagonists. Small lipophilic electron withdrawing substituents give potent but low efficacy compounds, while small polar electron donating substituents give potent and efficacious compounds. The activity of these compounds is described in terms of a model of the receptor involving lipophilic and hydrogen bonding interactions. These compounds provide muscarinic ligands with high potency and a range of efficacies suitable for testing as candidate drugs in the treatment of Alzheimer's disease.

  DOI：

  10.1021/jm00091a007

文献信息

• Azabicyclic compounds for treating dementia
  申请人：Beecham Group p.l.c.

  公开号：US05217975A1

  公开（公告）日：1993-06-08

  A compound of formula (I) useful for treating dementia or a pharmaceutically acceptable salt thereof: ##STR1## in which one of X and Y represents hydrogen and the other represents Z, where Z is a group in which Q represents a 3-membered divalent residue completing a 5-membered aromatic ring and comprises two or three nitrogen atoms, any amino nitrogen being substituted by a C.sub.1-2 alkyl, cyclopropyl or propargyl group, r represents the integer of 2 or 3, s represents an integer of 1 or 2 and t represents 0, with the proviso that when Y is hydrogen s is 1.

  一种化合物的分子式（I），或其药学上可接受的盐，可用于治疗痴呆症：##STR1## 其中X和Y中的一个表示氢，另一个表示Z，其中Z是一个基团，其中Q表示完成5-成员芳香环的3-成员二价残基，并包括两个或三个氮原子，任何氨基氮均被C.sub.1-2烷基，环丙基或丙炔基取代，r表示2或3的整数，s表示1或2的整数，t表示0，但当Y为氢时，s为1。
• Azabicyclic compounds, process for their preparation and pharmaceutical compositions containing them
  申请人：Beecham Group p.l.c.

  公开号：EP0402056A2

  公开（公告）日：1990-12-12

  A compound of formula (I) or a pharmaceutically acceptable salt thereof: in which one of X and Y represents hydrogen and the other represents Z, where Z is a group in which Q represents a 3-membered divalent residue completing a 5-membered aromatic ring and comprises two or three nitrogen atoms, any amino nitrogen being substituted by a C1-2 alkyl, cyclopropyl or propargyl group, r represents an integer of 2 or 3, s represents an integer of 1 or 2 and t represents 0 or 1, with the proviso that when Y is hydrogen s is 1.

  式 (I) 的化合物或其药学上可接受的盐： 其中 X 和 Y 的一个代表氢，另一个代表 Z，其中 Z 是一个基团 其中 Q 代表完成五元芳香环的三元二价残基，包含两个或三个氮原子，任何氨基氮均被 C1-2 烷基、环丙基或丙炔基取代，r 代表 2 或 3 的整数，s 代表 1 或 2 的整数，t 代表 0 或 1，但当 Y 为氢时，s 为 1。
• US5217975A
  申请人：——

  公开号：US5217975A

  公开（公告）日：1993-06-08