1-(2-bromoethoxy)-2-(methylsulfanyl)benzene | 1341104-70-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 1-(2-bromoethoxy)-2-(methylsulfanyl)benzene
• 英文别名: 1-(2-Bromoethoxy)-2-(methylsulfanyl) benzene；1-(2-bromoethoxy)-2-methylsulfanylbenzene
• CAS: 1341104-70-8
• 化学式: C₉H₁₁BrOS
• 分子量: 247.156
• InChiKey: QZGDZOGTMJXDIC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  12
• 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：
  34.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  邻乙氧基苯甲酰氯 、 1-(2-bromoethoxy)-2-(methylsulfanyl)benzene 、 1-叔丁氧羰基-4-氨甲基哌啶 在 polystyrene carboxaldehyde resin 、 sodium cyanoborohydride 、 溶剂黄146 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 26.0h， 生成 2-ethoxy-N-[[1-[2-(2-methylsulfanylphenoxy)ethyl]piperidin-4-yl]methyl]benzamide
  参考文献：
  名称：

  The multiobjective based design, synthesis and evaluation of the arylsulfonamide/amide derivatives of aryloxyethyl- and arylthioethyl- piperidines and pyrrolidines as a novel class of potent 5-HT7 receptor antagonists

  摘要：

  An analysis of the virtual combinatorial library was used for refining a pilot set of 34 derivatives and designing a targeted 38-member library of the arylamide and arylsulfonamide derivatives of aryloxyethyl- and arylthioethyl-piperidines and pyrrolidines. All compounds 24-95 were synthesized according to an elaborated parallel solid-phase method and were biologically evaluated for their affinity for 5-HT7R. Additionally, the targeted library members were tested for 5-HT1A, 5-HT6, and D-2 receptors. Selected compounds of particular interest were examined for their intrinsic activity at 5-HT7R in vitro employing a cAMP assay. The study allowed us to identify compound 68 (4-fluoro-N-(1-{2-[(propan-2-yl)phenoxylethyl}piperidin-4-yl) benzenesulfonamide) as a potent 5-HT7R ligand (K-i = 0.3 nM) with strong antagonistic properties (K-b = 1 nM) and a 1450-fold selectivity over 5-HT(1A)Rs. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.07.043
• 作为产物：
  描述：

  2-羟基茴香硫醚 、 1,2-二溴乙烷 在 potassium carbonate 、 potassium iodide 作用下， 以 丙酮 为溶剂， 以42%的产率得到1-(2-bromoethoxy)-2-(methylsulfanyl)benzene
  参考文献：
  名称：

  The multiobjective based design, synthesis and evaluation of the arylsulfonamide/amide derivatives of aryloxyethyl- and arylthioethyl- piperidines and pyrrolidines as a novel class of potent 5-HT7 receptor antagonists

  摘要：

  An analysis of the virtual combinatorial library was used for refining a pilot set of 34 derivatives and designing a targeted 38-member library of the arylamide and arylsulfonamide derivatives of aryloxyethyl- and arylthioethyl-piperidines and pyrrolidines. All compounds 24-95 were synthesized according to an elaborated parallel solid-phase method and were biologically evaluated for their affinity for 5-HT7R. Additionally, the targeted library members were tested for 5-HT1A, 5-HT6, and D-2 receptors. Selected compounds of particular interest were examined for their intrinsic activity at 5-HT7R in vitro employing a cAMP assay. The study allowed us to identify compound 68 (4-fluoro-N-(1-{2-[(propan-2-yl)phenoxylethyl}piperidin-4-yl) benzenesulfonamide) as a potent 5-HT7R ligand (K-i = 0.3 nM) with strong antagonistic properties (K-b = 1 nM) and a 1450-fold selectivity over 5-HT(1A)Rs. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.07.043

文献信息

• The multiobjective based design, synthesis and evaluation of the arylsulfonamide/amide derivatives of aryloxyethyl- and arylthioethyl- piperidines and pyrrolidines as a novel class of potent 5-HT7 receptor antagonists
  作者：Paweł Zajdel、Rafał Kurczab、Katarzyna Grychowska、Grzegorz Satała、Maciej Pawłowski、Andrzej J. Bojarski

  DOI：10.1016/j.ejmech.2012.07.043

  日期：2012.10

  An analysis of the virtual combinatorial library was used for refining a pilot set of 34 derivatives and designing a targeted 38-member library of the arylamide and arylsulfonamide derivatives of aryloxyethyl- and arylthioethyl-piperidines and pyrrolidines. All compounds 24-95 were synthesized according to an elaborated parallel solid-phase method and were biologically evaluated for their affinity for 5-HT7R. Additionally, the targeted library members were tested for 5-HT1A, 5-HT6, and D-2 receptors. Selected compounds of particular interest were examined for their intrinsic activity at 5-HT7R in vitro employing a cAMP assay. The study allowed us to identify compound 68 (4-fluoro-N-(1-2-[(propan-2-yl)phenoxylethyl}piperidin-4-yl) benzenesulfonamide) as a potent 5-HT7R ligand (K-i = 0.3 nM) with strong antagonistic properties (K-b = 1 nM) and a 1450-fold selectivity over 5-HT(1A)Rs. (C) 2012 Elsevier Masson SAS. All rights reserved.