{3-[2-(2-氯苯氧基甲基)-苯并咪唑-1-基]-丙基}-二乙基-胺 | 1023698-77-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 中文名称: {3-[2-(2-氯苯氧基甲基)-苯并咪唑-1-基]-丙基}-二乙基-胺
• 英文名称: {3-[2-(2-chlorophenoxymethyl)-benzimidazol-1-yl]-propyl}-diethyl-amine
• 英文别名: 3-[2-[(2-chlorophenoxy)methyl]benzimidazol-1-yl]-N,N-diethylpropan-1-amine
• CAS: 1023698-77-2
• 化学式: C₂₁H₂₆ClN₃O
• 分子量: 371.91
• InChiKey: OVHKNDOXGQHSBR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  26
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  30.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  邻氯苯氧乙酸 、 N¹-[3-(diethylamino)propyl]-1,2-phenylenediamine 在 N,N'-羰基二咪唑 、 溶剂黄146 作用下， 以 二氯甲烷 为溶剂， 反应 22.0h， 生成 {3-[2-(2-氯苯氧基甲基)-苯并咪唑-1-基]-丙基}-二乙基-胺
  参考文献：
  名称：

  Parallel synthesis of a series of potentially brain penetrant aminoalkyl benzoimidazoles

  摘要：

  Alpha7 agonists were identified via GOLD (CCDC) docking in the putative agonist binding site of an alpha7 homology model and a series of aminoalkyl benzoimidazoles was synthesised to obtain potentially brain penetrant drugs. The array was prepared starting from the reaction of ortho-fluoronitrobenzenes with a selection of diamines, followed by reduction of the nitro group to obtain a series of monoalkylated phenylene diamines. N,N'-Carbonyidiimidazole (CDI) mediated acylation, followed by a parallel automated work-up procedure, afforded the monoacylated phenylenediamines which were cyclised under acidic conditions. Parallel work-up and purification afforded the array products in good yields and purities with a robust parallel methodology which will be useful for other libraries. Screening for alpha7 activity revealed compounds with agonist activity for the receptor. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.11.068

文献信息

• Parallel synthesis of a series of potentially brain penetrant aminoalkyl benzoimidazoles
  作者：Iolanda Micco、Arianna Nencini、Joanna Quinn、Hendrick Bothmann、Chiara Ghiron、Alessandro Padova、Silvia Papini

  DOI：10.1016/j.bmc.2007.11.068

  日期：2008.3

  Alpha7 agonists were identified via GOLD (CCDC) docking in the putative agonist binding site of an alpha7 homology model and a series of aminoalkyl benzoimidazoles was synthesised to obtain potentially brain penetrant drugs. The array was prepared starting from the reaction of ortho-fluoronitrobenzenes with a selection of diamines, followed by reduction of the nitro group to obtain a series of monoalkylated phenylene diamines. N,N'-Carbonyidiimidazole (CDI) mediated acylation, followed by a parallel automated work-up procedure, afforded the monoacylated phenylenediamines which were cyclised under acidic conditions. Parallel work-up and purification afforded the array products in good yields and purities with a robust parallel methodology which will be useful for other libraries. Screening for alpha7 activity revealed compounds with agonist activity for the receptor. (C) 2007 Elsevier Ltd. All rights reserved.