(-)-1-{[(7R,9S)-9-hydroxy-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridin-7-yl]methyl}-4-(2-methylphenyl)piperazine | 1039359-16-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: (-)-1-{[(7R,9S)-9-hydroxy-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridin-7-yl]methyl}-4-(2-methylphenyl)piperazine
• 英文别名: (7R,9S)-7-((4-o-tolylpiperazin-1-yl)methyl)-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridin-9-ol；(7R,9S)-7-[[4-(2-methylphenyl)piperazin-1-yl]methyl]-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridin-9-ol
• CAS: 1039359-16-4
• 化学式: C₂₂H₂₉N₃O
• 分子量: 351.492
• InChiKey: QVMYFGSETVJBSQ-NQIIRXRSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  26
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  39.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 生成 (-)-1-{[(7R,9S)-9-hydroxy-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridin-7-yl]methyl}-4-(2-methylphenyl)piperazine
  参考文献：
  名称：

  A Novel Class of Cycloalkano[b]pyridines as Potent and Orally Active Opioid Receptor-like 1 Antagonists with Minimal Binding Affinity to the hERG K⁺Channel

  摘要：

  A series of compounds based on 7-{[4-(2-methylphenyl)piperidin-1-yl]methyl}-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridine-9-ol ((-)-8b), a potent and selective opioid receptor-like 1 (ORL1) antagonist, was prepared and evaluated using structure-activity relationship studies with the aim of removing its affinity to human ether-a-go-go related gene (hERG) K+ channel. From these studies, 10l was identified as an optimized structure with respect to ORL1 antagonist activity, and affinity to the hERG K+ channel. Furthermore, 10l showed good in vivo antagonism with a wide therapeutic index in regards to adverse cardiovascular effects.

  DOI：

  10.1021/jm701590h