8-<3-propyl>-8-azaspiro<4.5>decane-7,9-dione | 155787-17-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氮杂螺癸烷衍生物
• 英文名称: 8-<3-propyl>-8-azaspiro<4.5>decane-7,9-dione
• 英文别名: 8-[3-[(5-methoxy-3,4-dihydro-2H-chromen-3-yl)amino]propyl]-8-azaspiro[4.5]decane-7,9-dione
• CAS: 155787-17-0
• 化学式: C₂₂H₃₀N₂O₄
• 分子量: 386.491
• InChiKey: WGWWYJRTUIUPFE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  67.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-碘代丙烷 、 8-<3-propyl>-8-azaspiro<4.5>decane-7,9-dione 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以52%的产率得到8-<3-propyl>-8-azaspiro<4.5>decane-7,9-dione
  参考文献：
  名称：

  3,4-Dihydro-3-amino-2H-1-benzopyran Derivatives as 5-HT1A Receptor Ligands and Potential Anxiolytic Agents. 1. Synthesis and Structure-Activity Relationship Studies

  摘要：

  A series of 3,4-dihydro-3-amino-2H-1-benzopyran derivatives were prepared in order to determine the necessary structural requirements for good affinity for 5-HT1A receptors and high selectivity versus other receptors. Modifications of the extracyclic amino substituents, the length of the alkyl side chains, and their substituents were explored. The best compounds (9g, 9k, 15b, 15d) possess imido or sulfonamido functional groups with, a preferential length of four methylenes for the side chain. After resolution, the dextrorotatory enantiomers showed better affinity and selectivity for 5-HT1A receptors. These compounds have been proven to be full agonists. 9g and its enantiomers showed anxiolytic activity in vivo in various comportemental models. The compound (+)-9g is currently under clinical investigation.

  DOI：

  10.1021/jm00038a007
• 作为产物：
  描述：

  3,3-四亚甲基戊二酰亚胺 在 potassium carbonate 、 三乙胺 、 potassium iodide 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 30.0h， 生成 8-<3-propyl>-8-azaspiro<4.5>decane-7,9-dione
  参考文献：
  名称：

  3,4-Dihydro-3-amino-2H-1-benzopyran Derivatives as 5-HT1A Receptor Ligands and Potential Anxiolytic Agents. 1. Synthesis and Structure-Activity Relationship Studies

  摘要：

  A series of 3,4-dihydro-3-amino-2H-1-benzopyran derivatives were prepared in order to determine the necessary structural requirements for good affinity for 5-HT1A receptors and high selectivity versus other receptors. Modifications of the extracyclic amino substituents, the length of the alkyl side chains, and their substituents were explored. The best compounds (9g, 9k, 15b, 15d) possess imido or sulfonamido functional groups with, a preferential length of four methylenes for the side chain. After resolution, the dextrorotatory enantiomers showed better affinity and selectivity for 5-HT1A receptors. These compounds have been proven to be full agonists. 9g and its enantiomers showed anxiolytic activity in vivo in various comportemental models. The compound (+)-9g is currently under clinical investigation.

  DOI：

  10.1021/jm00038a007

文献信息

• 3,4-Dihydro-3-amino-2H-1-benzopyran Derivatives as 5-HT1A Receptor Ligands and Potential Anxiolytic Agents. 1. Synthesis and Structure-Activity Relationship Studies
  作者：Tchao Podona、Beatrice Guardiola-Lemaitre、Daniel-Henri Caignard、Gerard Adam、Bruno Pfeiffer、Pierre Renard、Gerald Guillaumet

  DOI：10.1021/jm00038a007

  日期：1994.6

  A series of 3,4-dihydro-3-amino-2H-1-benzopyran derivatives were prepared in order to determine the necessary structural requirements for good affinity for 5-HT1A receptors and high selectivity versus other receptors. Modifications of the extracyclic amino substituents, the length of the alkyl side chains, and their substituents were explored. The best compounds (9g, 9k, 15b, 15d) possess imido or sulfonamido functional groups with, a preferential length of four methylenes for the side chain. After resolution, the dextrorotatory enantiomers showed better affinity and selectivity for 5-HT1A receptors. These compounds have been proven to be full agonists. 9g and its enantiomers showed anxiolytic activity in vivo in various comportemental models. The compound (+)-9g is currently under clinical investigation.