(-)-Spiroxatrine | 115649-80-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: (-)-Spiroxatrine
• 英文别名: Lopac-S-103；8-[[(3S)-2,3-dihydro-1,4-benzodioxin-3-yl]methyl]-1-phenyl-1,3,8-triazaspiro[4.5]decan-4-one
• CAS: 115649-80-4
• 化学式: C₂₂H₂₅N₃O₃
• 分子量: 379.459
• InChiKey: JVGBTTIJPBFLTE-SFHVURJKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  28
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  54
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  (S)-2-羟甲基-1,4-苯并二恶烷 以 吡啶 、 二甲基亚砜 为溶剂， 反应 72.0h， 生成 (-)-Spiroxatrine
  参考文献：
  名称：

  Serotonergic properties of spiroxatrine enantiomers

  摘要：

  The neuroleptic drug spiperone (1) has proven very useful in the characterization of putative serotonin (5-hydroxytryptamine, 5-HT) receptors. Thus, 5-HT1 receptors have been divided into subtypes based on their affinities for 1: 5-HT1A sites have high affinity, while 5-HT1B sites have low affinity. However, the usefulness of 1 for the pharmacological characterization of 5-HT1A sites is limited because of its high affinity for 5-HT2 (as well as D2-dopaminergic) receptors. A close analogue of 1, (+/-)-spiroxatrine (2), has much higher affinity for 5-HT1A receptors and much lower affinity for 5-HT2 receptors. We report here the stereospecific synthesis of (R)-(+)- and (S)-(-)-spiroxatrine enantiomers and their evaluation at several 5-HT receptors and D2-dopaminergic and alpha 1-adrenergic receptors.

  DOI：

  10.1021/jm00118a017

文献信息

• NIKAM, SHAM S.;MARTIN, ARNOLD R.;NELSON, DAVID L., J. MED. CHEM., 31,(1988) N 10, C. 1965-1968
  作者：NIKAM, SHAM S.、MARTIN, ARNOLD R.、NELSON, DAVID L.

  DOI：——

  日期：——
• Serotonergic properties of spiroxatrine enantiomers
  作者：Sham S. Nikam、Arnold R. Martin、David L. Nelson

  DOI：10.1021/jm00118a017

  日期：1988.10

  The neuroleptic drug spiperone (1) has proven very useful in the characterization of putative serotonin (5-hydroxytryptamine, 5-HT) receptors. Thus, 5-HT1 receptors have been divided into subtypes based on their affinities for 1: 5-HT1A sites have high affinity, while 5-HT1B sites have low affinity. However, the usefulness of 1 for the pharmacological characterization of 5-HT1A sites is limited because of its high affinity for 5-HT2 (as well as D2-dopaminergic) receptors. A close analogue of 1, (+/-)-spiroxatrine (2), has much higher affinity for 5-HT1A receptors and much lower affinity for 5-HT2 receptors. We report here the stereospecific synthesis of (R)-(+)- and (S)-(-)-spiroxatrine enantiomers and their evaluation at several 5-HT receptors and D2-dopaminergic and alpha 1-adrenergic receptors.