2-(2-chloro-6-methoxyphenoxy)ethylamine | 914454-98-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2-(2-chloro-6-methoxyphenoxy)ethylamine
• 英文别名: 2-(2-chloro-6-methoxyphenoxy)ethanamine；2-(2-Chloro-6-methoxyphenoxy)ethan-1-amine
• CAS: 914454-98-1
• 化学式: C₉H₁₂ClNO₂
• 分子量: 201.653
• InChiKey: YFOXYCIAKLKOIJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  44.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(2-chloro-6-methoxyphenoxy)ethylamine 、 2-(2-(benzyloxy)phenoxy)acetic acid 在 氯甲酸乙酯 、 三乙胺 作用下， 以 氯仿 为溶剂， 反应 3.5h， 以76%的产率得到2-(2-(benzyloxy)phenoxy)-N-(2-(2-chloro-6-methoxy phenoxy)ethyl)acetamide
  参考文献：
  名称：

  Structure–activity relationships in 1,4-benzodioxan-related compounds. 10. Novel α1-adrenoreceptor antagonists related to openphendioxan: Synthesis, biological evaluation, and α1d computational study

  摘要：

  A series of novel openphendioxan analogues were synthesized and tested at alpha(1)-adrenoreceptor (AR) subtypes by binding and functional assays. The alpha(1d)-AR binding profile was also examined by means of 2D, 3D-QSAR together with docking studies. Multiple regression analysis suggested the relevance of adequate number of heteroatoms in the whole molecule and of passive membrane diffusion to enhance alpha(1d)-AR affinity. Docking simulations against a computational structural model of the biological target further proved this evidence and furnished support for chemiometric analysis, where polar, electrostatic, hydrophobic and shape effects of the ortho substituents in the phenoxy terminal, most likely governing ligand binding, helped the depiction of pharmacophore hypothesis for the examined ligands data set. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.08.002
• 作为产物：
  描述：

  2-氯-6-甲氧基苯酚 在 氢氧化钾 、 一水合肼 作用下， 以 乙二醇甲醚 、 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 反应 30.0h， 生成 2-(2-chloro-6-methoxyphenoxy)ethylamine
  参考文献：
  名称：

  QSAR study for a novel series of ortho disubstituted phenoxy analogues of α1-adrenoceptor antagonist WB4101

  摘要：

  On the basis of the affinities at the alpha(1a)-, alpha(1b)- and alpha(1d)-adrenoceptors and the 5-HT1A receptor of a previous series of sixteen 2-[(2-phenoxyethyl)aminomethyl]-1,4-benzodioxanes ortho monosubstituted at the phenoxy moiety, a number of ortho disubstituted analogues were designed, synthesized in both the enantiomeric forms and tested in binding assays on the same receptors. The affinity values of the new compounds 1-11 were compared with those of the enantiomers of the 2,6-dimethoxyphenoxy analogue, the well-known alpha 1 antagonist WB4101, and of the ortho monosubstituted derivatives, suggesting some distinctive aspects of the interaction of the phenoxy moiety, in particular with the alpha 1a-AR and the 5-HT1A receptor, of the monosubstituted and the disubstituted compounds. A classical quantitative structure-activity relationship (Hansch) analysis was applied to the whole set of the S enantiomers of the ortho mono- and disubstituted WB4101 analogues (26 compounds), finding a very good correlation for the a,, affinity. For this latter, a significant parabolic relationship was also found with the volume of the two ortho substituents. Diametrically opposite, the same relationships for the 5-HT1A exhibit low or insignificant correlation coefficients. (c) 2006 Elsevier SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2006.04.004

文献信息

• Structure–activity relationships in 1,4-benzodioxan-related compounds. 10. Novel α1-adrenoreceptor antagonists related to openphendioxan: Synthesis, biological evaluation, and α1d computational study
  作者：Antonio Carrieri、Alessandro Piergentili、Fabio Del Bello、Mario Giannella、Maria Pigini、Amedeo Leonardi、Francesca Fanelli、Wilma Quaglia

  DOI：10.1016/j.bmc.2010.08.002

  日期：2010.10

  A series of novel openphendioxan analogues were synthesized and tested at alpha(1)-adrenoreceptor (AR) subtypes by binding and functional assays. The alpha(1d)-AR binding profile was also examined by means of 2D, 3D-QSAR together with docking studies. Multiple regression analysis suggested the relevance of adequate number of heteroatoms in the whole molecule and of passive membrane diffusion to enhance alpha(1d)-AR affinity. Docking simulations against a computational structural model of the biological target further proved this evidence and furnished support for chemiometric analysis, where polar, electrostatic, hydrophobic and shape effects of the ortho substituents in the phenoxy terminal, most likely governing ligand binding, helped the depiction of pharmacophore hypothesis for the examined ligands data set. (C) 2010 Elsevier Ltd. All rights reserved.
• QSAR study for a novel series of ortho disubstituted phenoxy analogues of α1-adrenoceptor antagonist WB4101
  作者：M. Pallavicini、L. Fumagalli、M. Gobbi、C. Bolchi、S. Colleoni、B. Moroni、A. Pedretti、C. Rusconi、G. Vistoli、E. Valoti

  DOI：10.1016/j.ejmech.2006.04.004

  日期：2006.9

  On the basis of the affinities at the alpha(1a)-, alpha(1b)- and alpha(1d)-adrenoceptors and the 5-HT1A receptor of a previous series of sixteen 2-[(2-phenoxyethyl)aminomethyl]-1,4-benzodioxanes ortho monosubstituted at the phenoxy moiety, a number of ortho disubstituted analogues were designed, synthesized in both the enantiomeric forms and tested in binding assays on the same receptors. The affinity values of the new compounds 1-11 were compared with those of the enantiomers of the 2,6-dimethoxyphenoxy analogue, the well-known alpha 1 antagonist WB4101, and of the ortho monosubstituted derivatives, suggesting some distinctive aspects of the interaction of the phenoxy moiety, in particular with the alpha 1a-AR and the 5-HT1A receptor, of the monosubstituted and the disubstituted compounds. A classical quantitative structure-activity relationship (Hansch) analysis was applied to the whole set of the S enantiomers of the ortho mono- and disubstituted WB4101 analogues (26 compounds), finding a very good correlation for the a,, affinity. For this latter, a significant parabolic relationship was also found with the volume of the two ortho substituents. Diametrically opposite, the same relationships for the 5-HT1A exhibit low or insignificant correlation coefficients. (c) 2006 Elsevier SAS. All rights reserved.