exo-3-(3-methyl-1,2,4-triazol-1-yl)-1-azabicyclo<2.2.1>heptane | 136681-34-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: exo-3-(3-methyl-1,2,4-triazol-1-yl)-1-azabicyclo<2.2.1>heptane
• 英文别名: exo-3-(3-methyl-1,2,4-triazol-1-yl)-1-azabicyclo[2.2.1]heptane；(3R,4S)-3-(3-methyl-1,2,4-triazol-1-yl)-1-azabicyclo[2.2.1]heptane
• CAS: 136681-34-0；142482-96-0
• 化学式: C₉H₁₄N₄
• 分子量: 178.237
• InChiKey: KBTYGJMDMGMINJ-IUCAKERBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  34
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  甲基乙酰亚胺酯盐酸盐 、 (1-azabicyclo<2.2.1>heptan-3-yl)hydrazine dihydrochloride 、 原甲酸三乙酯 在 吡啶 、 三乙胺 作用下， 生成 exo-3-(3-methyl-1,2,4-triazol-1-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

• Substituent variation in azabicyclic triazole- and tetrazole-based muscarinic receptor ligands
  作者：Sarah M. Jenkins、Harry J. Wadsworth、Steven Bromidge、Barry S. Orlek、Paul A. Wyman、Graham J. Riley、Julie Hawkins

  DOI：10.1021/jm00091a007

  日期：1992.6

  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.