2-{(1S,4S)-5-[(2R)-3-(2-methoxyphenoxy)-2-hydroxypropyl]-2,5-diazabicyclo[2.2.1]heptan-2-yl}-N-(2,6-dimethylphenyl)acetamide | 1638211-20-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2-{(1S,4S)-5-[(2R)-3-(2-methoxyphenoxy)-2-hydroxypropyl]-2,5-diazabicyclo[2.2.1]heptan-2-yl}-N-(2,6-dimethylphenyl)acetamide
• 英文别名: N-(2,6-dimethylphenyl)-2-[(1S,4S)-5-[(2R)-2-hydroxy-3-(2-methoxyphenoxy)propyl]-2,5-diazabicyclo[2.2.1]heptan-2-yl]acetamide
• CAS: 1638211-20-7
• 化学式: C₂₅H₃₃N₃O₄
• 分子量: 439.555
• InChiKey: CXBBRGDUSKTENX-PCCBWWKXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  32
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  74.3
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  2-溴-N-(2,6-二甲苯基)乙酰胺 在 盐酸 、 palladium on activated charcoal 、 氢气 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 38.0h， 生成 2-{(1S,4S)-5-[(2R)-3-(2-methoxyphenoxy)-2-hydroxypropyl]-2,5-diazabicyclo[2.2.1]heptan-2-yl}-N-(2,6-dimethylphenyl)acetamide
  参考文献：
  名称：

  Synthesis of Ranolazine Derivatives Containing the (1S,4S)-2,5-Diazabicyclo[2.2.1]Heptane Moiety and Their Evaluation as Vasodilating Agents

  摘要：

  Two diazabicyclic analogues of ranolazine, (S,S,S)‐5 and (S,S,R)‐5, and their epimeric mixture were synthesized. Furthermore, their vasomotor effects on rat aorta rings precontracted with phenylephrine were analyzed. These compounds showed vasodilating effects significantly greater than ranolazine. The vasodilating activities of these analogues have two components, one that depends on the endothelium, due to the release of NO, and another one due to a direct effect on the vascular smooth muscle. The compounds [(S,S,S)(S,S,R)]‐5 and (S,S,R)‐5 induce, in a manner similar to ranolazine, the release of a prostanoid from the cyclooxygenase pathway, whose vasoconstrictor effect is masked by the predominant vasodilation induced by these compounds.

  DOI：

  10.1111/cbdd.12285

文献信息

• Synthesis of Ranolazine Derivatives Containing the (1<i>S</i>,4<i>S</i>)-2,5-Diazabicyclo[2.2.1]Heptane Moiety and Their Evaluation as Vasodilating Agents
  作者：Manuel López-Ortiz、Ivan Monsalvo、Patricia Demare、Cristina Paredes、Dieter Mascher、Carlos Hernández、Marcos Hernández、Ignacio Regla

  DOI：10.1111/cbdd.12285

  日期：2014.6

  Two diazabicyclic analogues of ranolazine, (S,S,S)‐5 and (S,S,R)‐5, and their epimeric mixture were synthesized. Furthermore, their vasomotor effects on rat aorta rings precontracted with phenylephrine were analyzed. These compounds showed vasodilating effects significantly greater than ranolazine. The vasodilating activities of these analogues have two components, one that depends on the endothelium, due to the release of NO, and another one due to a direct effect on the vascular smooth muscle. The compounds [(S,S,S)(S,S,R)]‐5 and (S,S,R)‐5 induce, in a manner similar to ranolazine, the release of a prostanoid from the cyclooxygenase pathway, whose vasoconstrictor effect is masked by the predominant vasodilation induced by these compounds.