6-(oxiran-2-ylmethoxy)-1H-indole | 70260-93-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 6-(oxiran-2-ylmethoxy)-1H-indole
• 英文别名: 6-[(oxiran-2-yl)methoxy]-1H-indole
• CAS: 70260-93-4
• 化学式: C₁₁H₁₁NO₂
• 分子量: 189.214
• InChiKey: FNAUUGIPMZMODT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  37.6
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-对羟基苯基哌嗪 、 6-(oxiran-2-ylmethoxy)-1H-indole 以 乙醇 为溶剂， 以32.1%的产率得到4-(4-(3-((1H-indol-6-yl)oxy)-2-hydroxypropyl)piperazin-1-yl)phenol
  参考文献：
  名称：

  Synthesis and evaluation of 4-(2-hydroxypropyl)piperazin-1-yl) derivatives as Hsp90 inhibitors

  摘要：

  We previously reported 4-(3-((6-bromonaphthalen-2-yl)oxy)-2-hydroxypropyl)-N,N-dimethylpiperazine- 1-sulfonamide (1) as a novel heat shock protein 90 inhibitor with moderate activity. In our ongoing efforts for the discovery of Hsp90 modulators we undertake structural investigations on 1. Series of the titled compound were designed, synthesized and evaluated. We have found that compounds with a hydroxyl group at C-4 of the aryl ring on the piperazine moiety possess Hsp90 inhibition properties. Compound 6f with improved activity could be further developed and optimized as Hsp90 inhibitor. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2016.03.049
• 作为产物：
  描述：

  6-羟基吲哚 、 环氧氯丙烷 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 9.0h， 以89.43%的产率得到6-(oxiran-2-ylmethoxy)-1H-indole
  参考文献：
  名称：

  Synthesis and evaluation of 4-(2-hydroxypropyl)piperazin-1-yl) derivatives as Hsp90 inhibitors

  摘要：

  We previously reported 4-(3-((6-bromonaphthalen-2-yl)oxy)-2-hydroxypropyl)-N,N-dimethylpiperazine- 1-sulfonamide (1) as a novel heat shock protein 90 inhibitor with moderate activity. In our ongoing efforts for the discovery of Hsp90 modulators we undertake structural investigations on 1. Series of the titled compound were designed, synthesized and evaluated. We have found that compounds with a hydroxyl group at C-4 of the aryl ring on the piperazine moiety possess Hsp90 inhibition properties. Compound 6f with improved activity could be further developed and optimized as Hsp90 inhibitor. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2016.03.049

文献信息

• US4146630A
  申请人：——

  公开号：US4146630A

  公开（公告）日：1979-03-27
• Synthesis and evaluation of 4-(2-hydroxypropyl)piperazin-1-yl) derivatives as Hsp90 inhibitors
  作者：Bahidja Cherfaoui、Tian-kun Guo、Hao-Peng Sun、Wei-Lin Cheng、Fang Liu、Fen Jiang、Xiao-Li Xu、Qi-Dong You

  DOI：10.1016/j.bmc.2016.03.049

  日期：2016.6

  We previously reported 4-(3-((6-bromonaphthalen-2-yl)oxy)-2-hydroxypropyl)-N,N-dimethylpiperazine- 1-sulfonamide (1) as a novel heat shock protein 90 inhibitor with moderate activity. In our ongoing efforts for the discovery of Hsp90 modulators we undertake structural investigations on 1. Series of the titled compound were designed, synthesized and evaluated. We have found that compounds with a hydroxyl group at C-4 of the aryl ring on the piperazine moiety possess Hsp90 inhibition properties. Compound 6f with improved activity could be further developed and optimized as Hsp90 inhibitor. (C) 2016 Elsevier Ltd. All rights reserved.