2-{[2-(4-Chlorophenoxy)ethoxy]methyl}oxirane | 540760-62-1

• 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-(4-Chlorophenoxy)ethoxy]methyl}oxirane
• 英文别名: 2-[2-(4-chlorophenoxy)ethoxymethyl]oxirane
• CAS: 540760-62-1
• 化学式: C₁₁H₁₃ClO₃
• mdl: MFCD04426769
• 分子量: 228.675
• InChiKey: OJQIRZPGAUHQII-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：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.454
• 拓扑面积：
  31
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(2-tert-butylphenyl)piperazine 、 2-{[2-(4-Chlorophenoxy)ethoxy]methyl}oxirane 在 乙醇 作用下， 反应 8.0h， 生成 1-(4-(2-(tert-butyl)phenyl)piperazin-1-yl)-3-(2-(4-chlorophenoxy)ethoxy)propan-2-ol
  参考文献：
  名称：

  Synthesis and evaluation of a novel class Hsp90 inhibitors containing 1-phenylpiperazine scaffold

  摘要：

  Previously, we identified 1-(2-(4-bromophenoxy) ethoxy)-3-(4-(2-methoxyphenyl) piperazin-1-yl) propan- 2-ol (1) as a novel Hsp90 inhibitor with moderate activity through virtual screening. In this study, we report the optimization process of 1. A series of analogues containing the 1-phenylpiperazine core scaffold were synthesized and evaluated. The structure-activity relationships (SAR) for these compounds was also discussed for further molecular design. This effort afforded the most active inhibitor 13f with improved activity in not only target-based level, but also cell-based level compared with the original hit 1. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.01.070
• 作为产物：
  描述：

  对氯苯酚 在 sodium hydride 、 sodium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 35.0h， 生成 2-{[2-(4-Chlorophenoxy)ethoxy]methyl}oxirane
  参考文献：
  名称：

  Synthesis and evaluation of a novel class Hsp90 inhibitors containing 1-phenylpiperazine scaffold

  摘要：

  Previously, we identified 1-(2-(4-bromophenoxy) ethoxy)-3-(4-(2-methoxyphenyl) piperazin-1-yl) propan- 2-ol (1) as a novel Hsp90 inhibitor with moderate activity through virtual screening. In this study, we report the optimization process of 1. A series of analogues containing the 1-phenylpiperazine core scaffold were synthesized and evaluated. The structure-activity relationships (SAR) for these compounds was also discussed for further molecular design. This effort afforded the most active inhibitor 13f with improved activity in not only target-based level, but also cell-based level compared with the original hit 1. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.01.070

文献信息

• MEISEL, PETER;LABAN, GUNTER;KRETZSCHMAR, EGON;REPKE, HEINRICH
  作者：MEISEL, PETER、LABAN, GUNTER、KRETZSCHMAR, EGON、REPKE, HEINRICH

  DOI：——

  日期：——
• Synthesis and evaluation of a novel class Hsp90 inhibitors containing 1-phenylpiperazine scaffold
  作者：Jian-Min Jia、Fang Liu、Xiao-Li Xu、Xiao-Ke Guo、Fen Jiang、Bahidja Cherfaoui、Hao-Peng Sun、Qi-Dong You

  DOI：10.1016/j.bmcl.2014.01.070

  日期：2014.3

  Previously, we identified 1-(2-(4-bromophenoxy) ethoxy)-3-(4-(2-methoxyphenyl) piperazin-1-yl) propan- 2-ol (1) as a novel Hsp90 inhibitor with moderate activity through virtual screening. In this study, we report the optimization process of 1. A series of analogues containing the 1-phenylpiperazine core scaffold were synthesized and evaluated. The structure-activity relationships (SAR) for these compounds was also discussed for further molecular design. This effort afforded the most active inhibitor 13f with improved activity in not only target-based level, but also cell-based level compared with the original hit 1. (C) 2014 Elsevier Ltd. All rights reserved.