(RS)-4-dimethylamino-2-(naphthalen-2-yl)butan-2-ol | 475578-85-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (RS)-4-dimethylamino-2-(naphthalen-2-yl)butan-2-ol
• 英文别名: 4-(Dimethylamino)-2-naphthalen-2-ylbutan-2-ol；4-(dimethylamino)-2-naphthalen-2-ylbutan-2-ol
• CAS: 475578-85-9
• 化学式: C₁₆H₂₁NO
• 分子量: 243.349
• InChiKey: GAOZGUXUGAZVAC-UHFFFAOYSA-N

物化性质

• 沸点：
  394.4±30.0 °C(Predicted)
• 密度：
  1.067±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  23.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (RS)-4-dimethylamino-2-(naphthalen-2-yl)butan-2-ol 在 palladium on activated charcoal 盐酸 、 氢气 作用下， 以 甲醇 、 乙醚 、 正戊烷 为溶剂， 反应 24.0h， 生成 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：

  2-溴萘 、 4-(二甲氨基)-2-丁酮 在 叔丁基锂 作用下， 以 乙醚 为溶剂， 反应 3.0h， 以62%的产率得到(RS)-4-dimethylamino-2-(naphthalen-2-yl)butan-2-ol
  参考文献：
  名称：

  具有止痛活性的外消旋和旋光性二烷基氨基烷基萘的化学和生物学特征

  摘要：

  二烷基氨基烷基萘的外消旋混合物和对映异构体在本文中被描述为新型镇痛剂，其功效与吗啡相似或更高。报道了纯对映异构体的合成和分离以及对绝对构型的研究。外消旋体的拆分通过使用Chiralpak AD柱的制备型液相色谱来完成。在对（+）-苄基-（3-羟基-3-萘-2-基-丁基）二甲基溴化铵的X射线晶体学分析以及CD和NOESY 1 H NMR的比较研究的基础上进行了构型分配拆分对映体的光谱。描述了通过热板试验对止痛活性的药理学评价。

  DOI：

  10.1016/s0957-4166(02)00241-0

文献信息

• Chemical and biological profile of racemic and optically active dialkylaminoalkylnaphthalenes with analgesic activity
  作者：Ornella Azzolina、Simona Collina、Gloria Brusotti、Daniela Rossi、Athos Callegari、Laura Linati、Annalisa Barbieri、Victor Ghislandi

  DOI：10.1016/s0957-4166(02)00241-0

  日期：2002.6

  enantiomers of dialkylaminoalkylnaphthalenes are described here as novel analgesic agents with potencies similar, or superior to that of morphine. The synthesis and isolation of the pure enantiomers and a study of the absolute configuration are reported. The resolution of racemates was accomplished by preparative liquid chromatography using a Chiralpak AD column. The configurational assignment was performed

  二烷基氨基烷基萘的外消旋混合物和对映异构体在本文中被描述为新型镇痛剂，其功效与吗啡相似或更高。报道了纯对映异构体的合成和分离以及对绝对构型的研究。外消旋体的拆分通过使用Chiralpak AD柱的制备型液相色谱来完成。在对（+）-苄基-（3-羟基-3-萘-2-基-丁基）二甲基溴化铵的X射线晶体学分析以及CD和NOESY 1 H NMR的比较研究的基础上进行了构型分配拆分对映体的光谱。描述了通过热板试验对止痛活性的药理学评价。
• 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.
• 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.