(R)-7-Dipropylamino-5,6,7,8-tetrahydro-indolizine-3-carbaldehyde | 400710-22-7

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (R)-7-Dipropylamino-5,6,7,8-tetrahydro-indolizine-3-carbaldehyde
• 英文别名: (7R)-7-(dipropylamino)-5,6,7,8-tetrahydroindolizine-3-carbaldehyde
• CAS: 400710-22-7
• 化学式: C₁₅H₂₄N₂O
• 分子量: 248.368
• InChiKey: RIOOLQVLOZQLQJ-CYBMUJFWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  25.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (R)-7-Dipropylamino-5,6,7,8-tetrahydro-indolizine-3-carbaldehyde 在 sodium tetrahydroborate 作用下， 以 异丙醇 为溶剂， 反应 19.0h， 生成 ((R)-7-Dipropylamino-5,6,7,8-tetrahydro-indolizin-3-yl)-methanol
  参考文献：
  名称：

  Dopaminergic 7-aminotetrahydroindolizines: ex-chiral pool synthesis and preferential D3 receptor binding

  摘要：

  Starting from both isomers of enantiopure asparagine, heterocyclic bioisosteres of the preferential dopamine D3 receptor agonist (R)-7-OH-DPAT were investigated when SAR studies led to the 3-formyl substituted aminoindolizine (S)-1e (FAUC 54) displaying a K-i value of 6.0 nM for the high affinity D3 binding site. In contrast, D3 affinity of the enantiomer (R)-1e was 300 fold lower. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(01)00564-9
• 作为产物：
  描述：

  (R)-7-N,N-dipropylamino-5,6,7,8-tetrahydroindolizine 、 N,N-二甲基甲酰胺 在 三氯氧磷 作用下， 反应 4.0h， 生成 (R)-7-Dipropylamino-5,6,7,8-tetrahydro-indolizine-3-carbaldehyde 、 (R)-7-Dipropylamino-5,6,7,8-tetrahydro-indolizine-1-carbaldehyde
  参考文献：
  名称：

  Dopaminergic 7-aminotetrahydroindolizines: ex-chiral pool synthesis and preferential D3 receptor binding

  摘要：

  Starting from both isomers of enantiopure asparagine, heterocyclic bioisosteres of the preferential dopamine D3 receptor agonist (R)-7-OH-DPAT were investigated when SAR studies led to the 3-formyl substituted aminoindolizine (S)-1e (FAUC 54) displaying a K-i value of 6.0 nM for the high affinity D3 binding site. In contrast, D3 affinity of the enantiomer (R)-1e was 300 fold lower. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(01)00564-9

文献信息

• CoMFA and CoMSIA Investigations Revealing Novel Insights into the Binding Modes of Dopamine D3 Receptor Agonists
  作者：Frank Boeckler、Ursula Ohnmacht、Thomas Lehmann、Wolfgang Utz、Harald Hübner、Peter Gmeiner

  DOI：10.1021/jm049269+

  日期：2005.4.1

  As an extension of a series of dopamine D(3) receptor agonists involving FAUC 54, ex-chiral pool synthesis, and biological evaluation of 3-substituted 7-aminotetrahydroindolizines was performed. Considering the structural features of both series of enantiomers, we developed a novel alignment hypothesis for D(3) agonists, allowing for the placement of the aromatic moieties on two alternative, adjacent

  作为一系列涉及FAUC 54的多巴胺D（3）受体激动剂的扩展，进行了手性池合成和3取代7-氨基四氢吲哚并嗪的生物学评估。考虑到这两个对映体系列的结构特征，我们为D（3）激动剂开发了一种新颖的比对假设，允许将芳香族部分放置在两个替代的相邻位置上。当新发明的控制路线选择的程序应用程序（IRAS）证明是有用的时，CoMFA和CoMSIA分析分别产生了显着的交叉验证q（2）值0.726和0.590。利用CoMFA / CoMSIA贡献图，我们能够将D（3）受体的先前构建的同源性模型从非活动状态转换为活动状态。除了已建立的离子相互作用，
• Dopaminergic 7-aminotetrahydroindolizines: ex-chiral pool synthesis and preferential D3 receptor binding
  作者：Thomas Lehmann、Harald Hübner、Peter Gmeiner

  DOI：10.1016/s0960-894x(01)00564-9

  日期：2001.11

  Starting from both isomers of enantiopure asparagine, heterocyclic bioisosteres of the preferential dopamine D3 receptor agonist (R)-7-OH-DPAT were investigated when SAR studies led to the 3-formyl substituted aminoindolizine (S)-1e (FAUC 54) displaying a K-i value of 6.0 nM for the high affinity D3 binding site. In contrast, D3 affinity of the enantiomer (R)-1e was 300 fold lower. (C) 2001 Elsevier Science Ltd. All rights reserved.