(E)-N,N-dimethyl[3-(naphthalen-2-yl)but-2-enyl]amine hydrochloride

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (E)-N,N-dimethyl[3-(naphthalen-2-yl)but-2-enyl]amine hydrochloride
• 英文别名: (E)-dimethyl(3-naphthalen-2-yl-but-2-enyl)amine hydrochloride；(E)-N,N-dimethyl-3-naphthalen-2-ylbut-2-en-1-amine;hydrochloride
• 化学式: C₁₆H₁₉N*ClH
• 分子量: 261.794
• InChiKey: FHPYVUGGMVOADC-RSGUCCNWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.23
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  3.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (E)-N,N-dimethyl[3-(naphthalen-2-yl)but-2-enyl]amine hydrochloride 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 反应 24.0h， 以59%的产率得到N,N-dimethyl[3-(naphthalen-2-yl)butyl]amine hydrochloride
  参考文献：
  名称：

  Design, synthesis, and SAR analysis of novel selective σ1 ligands

  摘要：

  A new series of arylalkyl- and alkenylamines was designed, synthesized, and evaluated for binding to sigma(1) and sigma(2) receptors. Many compounds exhibited nanomolar affinity for sigma(1) subtype receptor with good selectivity over sigma(2). A molecular modeling study was conducted in order to rationalize the experimental data, and the structure-receptor affinities are discussed. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.10.048
• 作为产物：
  描述：

  4-(二甲氨基)-2-丁酮 在 盐酸 、 叔丁基锂 作用下， 以 乙醚 、 正戊烷 为溶剂， 生成 (E)-N,N-dimethyl[3-(naphthalen-2-yl)but-2-enyl]amine hydrochloride
  参考文献：
  名称：

  Design, synthesis, and SAR analysis of novel selective σ1 ligands

  摘要：

  A new series of arylalkyl- and alkenylamines was designed, synthesized, and evaluated for binding to sigma(1) and sigma(2) receptors. Many compounds exhibited nanomolar affinity for sigma(1) subtype receptor with good selectivity over sigma(2). A molecular modeling study was conducted in order to rationalize the experimental data, and the structure-receptor affinities are discussed. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.10.048

文献信息

• Gaining in pan-affinity towards sigma 1 and sigma 2 receptors. SAR studies on arylalkylamines
  作者：Daniela Rossi、Marta Rui、Marcello Di Giacomo、Dirk Schepmann、Bernhard Wünsch、Stefania Monteleone、Klaus R. Liedl、Simona Collina

  DOI：10.1016/j.bmc.2016.10.005

  日期：2017.1

  Sigma Receptor (SR) modulators are involved in different signal transduction pathways, representing important pharmacological/therapeutic tools in several pathological conditions, such as neurodegenerative diseases and cancers. To this purpose, numerous compounds have been developed in order to target selectively one of the two subtypes (S1R and S2R) as chemotherapeutic agent. However, experiments have also shown that ligands which are able to bind both SR subtypes can be useful for the diagnosis and/or the treatment of cancers. Therefore, the discovery of compounds with good affinity towards both S1R and S2R ('pan-modulators') is also of great interest and still represents a challenge up to now. For this reason, we synthesized novel arylalkylamines with the aim to obtain compounds with S1R and S2R affinity in the nM range and, by modeling quantitative structure-activity relationships (QSARs), we identified the essential structural features to obtain promising pan-compounds. (C) 2016 Elsevier Ltd. All rights reserved.
• Design, synthesis, and SAR analysis of novel selective σ1 ligands
  作者：Simona Collina、Guya Loddo、Mariangela Urbano、Laura Linati、Athos Callegari、Francesco Ortuso、Stefano Alcaro、Christian Laggner、Thierry Langer、Orazio Prezzavento、Giuseppe Ronsisvalle、Ornella Azzolina

  DOI：10.1016/j.bmc.2006.10.048

  日期：2007.1

  A new series of arylalkyl- and alkenylamines was designed, synthesized, and evaluated for binding to sigma(1) and sigma(2) receptors. Many compounds exhibited nanomolar affinity for sigma(1) subtype receptor with good selectivity over sigma(2). A molecular modeling study was conducted in order to rationalize the experimental data, and the structure-receptor affinities are discussed. (c) 2006 Elsevier Ltd. All rights reserved.