Ethyl-(1-dimethylamino)cyclohexylacetat | 775222-59-8

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: Ethyl-(1-dimethylamino)cyclohexylacetat
• 英文别名: (1-Dimethylamino-cyclohexyl)-acetic acid ethyl ester；ethyl 2-[1-(dimethylamino)cyclohexyl]acetate
• CAS: 775222-59-8
• 化学式: C₁₂H₂₃NO₂
• 分子量: 213.32
• InChiKey: KMKODCKAYPYLBW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  Ethyl-(1-dimethylamino)cyclohexylacetat 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 生成 2-(1-dimethylamino-1-cyclohexyl)ethanol
  参考文献：
  名称：

  Carbamoylcholine homologs: synthesis and pharmacology at nicotinic acetylcholine receptors

  摘要：

  In a recent study, racemic 3-(N,N-dimethylamino)butyl-N,N-dimethylcarbamate (1) was shown to be a potent agonist at neuronal nicotinic acetylcholine receptors with a high selectivity for nicotinic over muscarinic acetylcholine receptors [Mol. Pharmacol. 64 (2003) 865-875]. Here we present the synthesis and pharmacological characterization of a series of analogs of 1, where the methyl group at C-3 has been replaced by different alkyl substituents. Ring systems have been incorporated into the carbon backbone of some of the molecules, or the amino group has been build into ring systems. Furthermore, the (+)- and (-)-enantiomers of I have been separated, and X-ray crystallography has revealed that (-)-1 possesses (S)-configuration. The compounds have been characterized pharmacologically at recombinant nicotinic receptor subtypes. The structure-activity relationship study has provided valuable insight into the mode of interactions of I and its analogs with neuronal nicotinic acetylcholine receptors. (C) 2004 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.ejphar.2004.06.038
• 作为产物：
  描述：

  环己烷亚基乙酸乙酯 、 二甲胺 生成 Ethyl-(1-dimethylamino)cyclohexylacetat
  参考文献：
  名称：

  Carbamoylcholine homologs: synthesis and pharmacology at nicotinic acetylcholine receptors

  摘要：

  In a recent study, racemic 3-(N,N-dimethylamino)butyl-N,N-dimethylcarbamate (1) was shown to be a potent agonist at neuronal nicotinic acetylcholine receptors with a high selectivity for nicotinic over muscarinic acetylcholine receptors [Mol. Pharmacol. 64 (2003) 865-875]. Here we present the synthesis and pharmacological characterization of a series of analogs of 1, where the methyl group at C-3 has been replaced by different alkyl substituents. Ring systems have been incorporated into the carbon backbone of some of the molecules, or the amino group has been build into ring systems. Furthermore, the (+)- and (-)-enantiomers of I have been separated, and X-ray crystallography has revealed that (-)-1 possesses (S)-configuration. The compounds have been characterized pharmacologically at recombinant nicotinic receptor subtypes. The structure-activity relationship study has provided valuable insight into the mode of interactions of I and its analogs with neuronal nicotinic acetylcholine receptors. (C) 2004 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.ejphar.2004.06.038

文献信息

• Carbamoylcholine homologs: synthesis and pharmacology at nicotinic acetylcholine receptors
  作者：Anders A. Jensen、Ivan Mikkelsen、Bente Frølund、Karla Frydenvang、Lotte Brehm、Jerzy W. Jaroszewski、Hans Bräuner-Osborne、Erik Falch、Povl Krogsgaard-Larsen

  DOI：10.1016/j.ejphar.2004.06.038

  日期：2004.8

  In a recent study, racemic 3-(N,N-dimethylamino)butyl-N,N-dimethylcarbamate (1) was shown to be a potent agonist at neuronal nicotinic acetylcholine receptors with a high selectivity for nicotinic over muscarinic acetylcholine receptors [Mol. Pharmacol. 64 (2003) 865-875]. Here we present the synthesis and pharmacological characterization of a series of analogs of 1, where the methyl group at C-3 has been replaced by different alkyl substituents. Ring systems have been incorporated into the carbon backbone of some of the molecules, or the amino group has been build into ring systems. Furthermore, the (+)- and (-)-enantiomers of I have been separated, and X-ray crystallography has revealed that (-)-1 possesses (S)-configuration. The compounds have been characterized pharmacologically at recombinant nicotinic receptor subtypes. The structure-activity relationship study has provided valuable insight into the mode of interactions of I and its analogs with neuronal nicotinic acetylcholine receptors. (C) 2004 Elsevier B.V. All rights reserved.