2-{[4-(1H-indol-2-yl)phenoxy]methyl}-5-phenyl-1,3,4-oxadiazole | 1357149-27-9

• 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: 2-{[4-(1H-indol-2-yl)phenoxy]methyl}-5-phenyl-1,3,4-oxadiazole
• 英文别名: 2-[[4-(1H-indol-2-yl)phenoxy]methyl]-5-phenyl-1,3,4-oxadiazole
• CAS: 1357149-27-9
• 化学式: C₂₃H₁₇N₃O₂
• 分子量: 367.407
• InChiKey: OCRPUAWBJWFWTN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  63.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-[4-(1H-indol-2-yl)phenoxy]acetohydrazide 、 苯甲酸 在 三氯氧磷 作用下， 反应 2.0h， 以63%的产率得到2-{[4-(1H-indol-2-yl)phenoxy]methyl}-5-phenyl-1,3,4-oxadiazole
  参考文献：
  名称：

  Synthesis, molecular docking study and antitumor activity of novel 2-phenylindole derivatives

  摘要：

  The starting material, 4-(1-indol-2-yl)phenol 1 was obtained via Fischer synthesis. Vilsmeir Haack's formylation of 1 gave the carboxaldehyde derivative 2 which was subjected to different reactions affording the 3-substituted compounds 3-10. Compound 1 reacted with halo esters to give 11 and 12a,b. The reaction of 12a with various amino derivatives gave compounds 13-16. The hydrazide derivative 15a reacted with 1,3-diketones, ethyl acetoacetate and aromatic carboxylic acid derivatives to give 17a,b, 18 and 19a-e, respectively. Antitumor activity of target compounds were tested against breast cancer cell lines (MCF-7) and (MDA-MB-231). The most potent compound was 3e with IC50 = 1.60 nM against (MCF-7). Docking was performed on colchicine binding site of tubulin to study the binding mode of the designed compounds. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.11.007

文献信息

• Synthesis, molecular docking study and antitumor activity of novel 2-phenylindole derivatives
  作者：Sally S. El-Nakkady、Mona M. Hanna、Hanaa M. Roaiah、Iman A.Y. Ghannam

  DOI：10.1016/j.ejmech.2011.11.007

  日期：2012.1

  The starting material, 4-(1-indol-2-yl)phenol 1 was obtained via Fischer synthesis. Vilsmeir Haack's formylation of 1 gave the carboxaldehyde derivative 2 which was subjected to different reactions affording the 3-substituted compounds 3-10. Compound 1 reacted with halo esters to give 11 and 12a,b. The reaction of 12a with various amino derivatives gave compounds 13-16. The hydrazide derivative 15a reacted with 1,3-diketones, ethyl acetoacetate and aromatic carboxylic acid derivatives to give 17a,b, 18 and 19a-e, respectively. Antitumor activity of target compounds were tested against breast cancer cell lines (MCF-7) and (MDA-MB-231). The most potent compound was 3e with IC50 = 1.60 nM against (MCF-7). Docking was performed on colchicine binding site of tubulin to study the binding mode of the designed compounds. (C) 2011 Elsevier Masson SAS. All rights reserved.