(2S)-6-(dipropylamino)-5,6,7,8-tetrahydronaphthalen-1-yl trifluoromethanesulfonate | 735279-23-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: (2S)-6-(dipropylamino)-5,6,7,8-tetrahydronaphthalen-1-yl trifluoromethanesulfonate
• 英文别名: (S)-2-(dipropylamino)-5-(trifluoromethanesulfonyloxy)tetralin；[(6S)-6-(dipropylamino)-5,6,7,8-tetrahydronaphthalen-1-yl] trifluoromethanesulfonate
• CAS: 735279-23-9
• 化学式: C₁₇H₂₄F₃NO₃S
• 分子量: 379.444
• InChiKey: GQWGKLIYDKGPRT-AWEZNQCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  55
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2,6-二甲氧基苯硼酸 、 (2S)-6-(dipropylamino)-5,6,7,8-tetrahydronaphthalen-1-yl trifluoromethanesulfonate 在 四(三苯基膦)钯 、 sodium carbonate 、 lithium chloride 作用下， 以 乙醇 、 甲苯 为溶剂， 反应 6.0h， 以91%的产率得到[(S)-5-(2,6-Dimethoxy-phenyl)-1,2,3,4-tetrahydro-naphthalen-2-yl]-dipropyl-amine
  参考文献：
  名称：

  Novel 2-Aminotetralin and 3-AminoChroman Derivatives as Selective Serotonin 5-HT₇ Receptor Agonists and Antagonists

  摘要：

  The understanding of the physiological role of the G-protein coupled serotonin 5-HT7 receptor is largely rudimentary. Therefore, selective and potent pharmacological tools will add to the understanding of serotonergic effects mediated through this receptor. In this report, we describe two compound classes, chromans and tetralins, encompassing compounds with nanomolar affinity for the 5-HT7 receptor and with good selectivity. Within theses classes, we have discovered both agonists and antagonists that can be used for further understanding of the pharmacology of the 5-HT7 receptor.

  DOI：

  10.1021/jm0498102
• 作为产物：
  描述：

  (S)-5-甲氧基-N,N-二丙基-1,2,3,4-四氢萘-2-胺 在 三溴化硼 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 (2S)-6-(dipropylamino)-5,6,7,8-tetrahydronaphthalen-1-yl trifluoromethanesulfonate
  参考文献：
  名称：

  Novel 2-Aminotetralin and 3-AminoChroman Derivatives as Selective Serotonin 5-HT₇ Receptor Agonists and Antagonists

  摘要：

  The understanding of the physiological role of the G-protein coupled serotonin 5-HT7 receptor is largely rudimentary. Therefore, selective and potent pharmacological tools will add to the understanding of serotonergic effects mediated through this receptor. In this report, we describe two compound classes, chromans and tetralins, encompassing compounds with nanomolar affinity for the 5-HT7 receptor and with good selectivity. Within theses classes, we have discovered both agonists and antagonists that can be used for further understanding of the pharmacology of the 5-HT7 receptor.

  DOI：

  10.1021/jm0498102

文献信息

• Synthesis of novel 5-substituted-2-aminotetralin analogs: 5-HT1A and 5-HT7 G protein-coupled receptor affinity, 3D-QSAR and molecular modeling
  作者：Charles K. Perry、Austen B. Casey、Daniel E. Felsing、Rajender Vemula、Mehreen Zaka、Noah B. Herrington、Meng Cui、Glen E. Kellogg、Clinton E. Canal、Raymond G. Booth

  DOI：10.1016/j.bmc.2019.115262

  日期：2020.2

  5-HT7 + or 5-HT1A receptors, several with modest selectivity (up to 12-fold) for binding at 5-HT7, and, several ligands with high selectivity (up to 40-fold) at the 5-HT1A receptor. 3D-QSAR results indicate that steric extensions at the C(5)-position improve selectivity for the 5-HT7 over 5-HT1A receptor, while steric and hydrophobic extensions at the chiral C(2)-amino position impart 5-HT1A selectivity

  血清素5-HT7 G蛋白偶联受体（GPCR）是针对各种中枢和外周适应症的拟议药物治疗靶标，尽管尚无批准的选择性结合5-HT7的药物。我们先前曾报道，基于5-取代-N，N-二取代-1,2,3,4-四氢萘-2-胺（5-取代-2-氨基四氢萘，5-SAT）支架的前导类似物与在5-HT7 GPCR上具有亲和力，并且可以治疗小鼠模型中的自闭症症状；随后，发现该铅对5-HT1A GPCR具有高亲和力。在这里，我们报告了新型5-SAT类似物的合成，以在人5-HT7受体上建立三维定量结构亲和关系（3D-QSAR），用于与在高度同源的5-HT1A受体上进行的类似研究进行比较。我们报告了35种新的5-SAT配体，一些对5-HT7 +或5-HT1A受体具有极高的亲和力（Ki≤1 nM）和立体选择性，另一些对与5-HT7结合具有适度的选择性（最高12倍），而一些对配体的选择性高（在5-HT1A受体上最多可扩增40倍