3-(1-methyl-1-azabicyclo<2.2.2>octyl) 2-hydroxy-3-(4-morpholinyl)-2-phenylpropionate iodide | 122846-70-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 奎宁环
• 英文名称: 3-(1-methyl-1-azabicyclo<2.2.2>octyl) 2-hydroxy-3-(4-morpholinyl)-2-phenylpropionate iodide
• 英文别名: (1-Methyl-1-azoniabicyclo[2.2.2]octan-3-yl) 2-hydroxy-3-morpholin-4-yl-2-phenylpropanoate;iodide
• CAS: 122846-70-2
• 化学式: C₂₁H₃₁N₂O₄*I
• 分子量: 502.393
• InChiKey: KEUICZCICLRJLT-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -2.01
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  59
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  ethyl 2-hydroxy-3-(4-morpholinyl)-2-phenylpropionate 在 sodium 作用下， 以 乙醚 为溶剂， 反应 43.0h， 生成 3-(1-methyl-1-azabicyclo<2.2.2>octyl) 2-hydroxy-3-(4-morpholinyl)-2-phenylpropionate iodide
  参考文献：
  名称：

  Synthesis of some 3-(1-azabicyclo[2.2.2]octyl) 3-amino-2-hydroxy-2-phenylpropionates: profile of antimuscarinic efficacy and selectivity

  摘要：

  A series of 3-quinuclidinyl atrolactate [3-(1-azabicyclo[2.2.2]octyl) 2-hydroxy-2-phenylpropionate, QNA] derivatives in which the methyl group of the parent is substituted with a tertiary amino substituent was prepared and tested for antimuscarinic activity. In general, potency was markedly decreased, although the morpholinyl and thiomorpholinyl derivatives retained significant activity. These compounds were also examined for muscarinic receptor subtype selectivity. Their subtype selectivities were comparable to that of (R,R)-QNA. The results of this investigation suggest possible differences in the accessory binding sites of the proteinaceous receptor subtypes.

  DOI：

  10.1021/jm00163a050

文献信息

• US4843074A
  申请人：——

  公开号：US4843074A

  公开（公告）日：1989-06-27
• Synthesis of some 3-(1-azabicyclo[2.2.2]octyl) 3-amino-2-hydroxy-2-phenylpropionates: profile of antimuscarinic efficacy and selectivity
  作者：Vicki H. Audia、Daniel W. McPherson、Moshe Weitzberg、W. Janusz Rzeszotarski、Bonnie Sturm、James F. Kachur、Mary Abreu、Carl Kaiser

  DOI：10.1021/jm00163a050

  日期：1990.1

  A series of 3-quinuclidinyl atrolactate [3-(1-azabicyclo[2.2.2]octyl) 2-hydroxy-2-phenylpropionate, QNA] derivatives in which the methyl group of the parent is substituted with a tertiary amino substituent was prepared and tested for antimuscarinic activity. In general, potency was markedly decreased, although the morpholinyl and thiomorpholinyl derivatives retained significant activity. These compounds were also examined for muscarinic receptor subtype selectivity. Their subtype selectivities were comparable to that of (R,R)-QNA. The results of this investigation suggest possible differences in the accessory binding sites of the proteinaceous receptor subtypes.