quinidine | 344899-23-6

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 金鸡纳生物碱
• 英文名称: quinidine
• 英文别名: Sdccgsbi-0051001.P002；(S)-[(2S,4R,5R)-5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl]-(6-methoxyquinolin-4-yl)methanol
• CAS: 344899-23-6
• 化学式: C₂₀H₂₄N₂O₂
• 分子量: 324.423
• InChiKey: LOUPRKONTZGTKE-ILWKUFEGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  45.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  quinidine 在 乙硫醇钠 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 2.0h， 生成
  参考文献：
  名称：

  Cation–π and π–π stacking interactions allow selective inhibition of butyrylcholinesterase by modified quinine and cinchonidine alkaloids

  摘要：

  Scaffold varied quaternized quinine and cinchonidine alkaloid derivatives were evaluated for their selective butyrylcholinesterase (BChE) inhibitory potential. K-i values were between 0.4-260.5 mu M (non-competitive inhibition) while corresponding K(i)values to acetylcholinesterase (AChE) ranged from 7.0-400 mu M exhibiting a 250-fold selectivity for BChE.Docking arrangements (GOLD. PLANT) revealed that the extended aromatic moieties and the quaternized nitrogen of the inhibitors were responsible for specific pi-pi stacking and pi-cation interactions with the choline binding site and the peripheral anionic site of BChE's active site. (C) 2010 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.bbrc.2010.12.084

文献信息

• The design, synthesis, and application of a chiral coupling reagent derived from strychnine for the enantioselective activation of a carboxylic group
  作者：Beata Kolesińska、Katarzyna Kasperowicz、Marek Sochacki、Adam Mazur、Stefan Jankowski、Zbigniew J. Kamiński

  DOI：10.1016/j.tetlet.2009.06.105

  日期：2010.1

  The concept of a chiral coupling reagent for the enantioselective synthesis of peptides with a predictable configuration and enantiomeric purity from racemic substrates is presented. The reagent was prepared by treatment of strychninium tetrafluoroborate with 2-chloro-4,6-dimethoxy-1,3,5-triazine in the presence of sodium bicarbonate yielding N-(4,6-dimethoxy-1,3,5-triazin-2-yl)strychninium tetrafluoroborate

  提出了用于从外消旋底物中对映体选择性合成具有可预测构型和对映体纯度的肽的手性偶联剂的概念。在碳酸氢钠存在下，用2-氯-4,6-二甲氧基-1,3,5-三嗪处理四氟硼酸锶，制备N-（4,6-二甲氧基-1,3,5-三嗪。 -2-基）四氟硼酸锶在室温下稳定，在多种溶剂中均能以d的高收率高收率得到富集的Z-Ala-Phe-OMe（dr从95/5至60/40）从rac -Z-Ala-OH开始的丙氨酸残基的-构型。
• Optically active isomers of quinine and quinidine and their respective biological action
  申请人：——

  公开号：US20030212098A1

  公开（公告）日：2003-11-13

  The present invention provides methods for purifying, identifying and using optically active isomers of quinine and quinidine as well as compositions comprising such optically active isomers. Such optically active isomers having desired actions on cardiac sodium and potassium channel function substantially separable from undesirable effects on GI motility can be useful for more effective therapy of cardiac arrhythmias. Also disclosed are methods for assaying the levels of such isomers present in the biological fluids.

  本发明提供了纯化、鉴定和使用奎宁和奎尼丁的光学活性异构体的方法，以及包含这种光学活性异构体的组合物。这种光学活性异构体对心脏钠和钾通道功能的预期作用与对胃肠道蠕动的不良影响基本分离，可用于更有效地治疗心律失常。此外，还公开了用于检测生物液体中存在的此类异构体水平的方法。
• US6844355B2
  申请人：——

  公开号：US6844355B2

  公开（公告）日：2005-01-18
• Cation–π and π–π stacking interactions allow selective inhibition of butyrylcholinesterase by modified quinine and cinchonidine alkaloids
  作者：Sarfraz A. Nawaz、Muhammad Ayaz、Wolfgang Brandt、Ludger A. Wessjohann、Bernhard Westermann

  DOI：10.1016/j.bbrc.2010.12.084

  日期：2011.1

  Scaffold varied quaternized quinine and cinchonidine alkaloid derivatives were evaluated for their selective butyrylcholinesterase (BChE) inhibitory potential. K-i values were between 0.4-260.5 mu M (non-competitive inhibition) while corresponding K(i)values to acetylcholinesterase (AChE) ranged from 7.0-400 mu M exhibiting a 250-fold selectivity for BChE.Docking arrangements (GOLD. PLANT) revealed that the extended aromatic moieties and the quaternized nitrogen of the inhibitors were responsible for specific pi-pi stacking and pi-cation interactions with the choline binding site and the peripheral anionic site of BChE's active site. (C) 2010 Elsevier Inc. All rights reserved.