5-(5-hydroxyindol-2-yl)-3-phenyl-1,2,4-oxadiazole | 1253493-41-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 5-(5-hydroxyindol-2-yl)-3-phenyl-1,2,4-oxadiazole
• 英文别名: 2-(3-phenyl-1,2,4-oxadiazol-5-yl)-1H-indol-5-ol
• CAS: 1253493-41-2
• 化学式: C₁₆H₁₁N₃O₂
• 分子量: 277.282
• InChiKey: VDWUPJVTJUYPFJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  74.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  5-(5-methoxyindol-2-yl)-3-phenyl-1,2,4-oxadiazole 在 三溴化硼 、 水 作用下， 以 二氯甲烷 为溶剂， 以85%的产率得到5-(5-hydroxyindol-2-yl)-3-phenyl-1,2,4-oxadiazole
  参考文献：
  名称：

  Design, synthesis and pro-apoptotic antitumour properties of indole-based 3,5-disubstituted oxadiazoles

  摘要：

  A series of new indole-based 3,5-disubstituted 1,2,4-oxadiazoles has been designed and synthesised as potential pro-apoptotic antitumour agents, via the base-catalysed condensation reaction between substituted amidoximes and indole esters. Evaluation of antiproliferative activity against the human cancer cell lines COLO 320 (colorectal) and MIA PACA-2 (pancreatic) revealed IC50 values in the low micromolar range. Selected compounds were able to trigger apoptosis in sensitive cell lines, for example via activation of caspase-3/7, demonstrating that indole-based oxadiazoles possess in vitro antitumour and pro-apoptotic activity. (C) 2010 Elsevier Masson SAS All rights reserved.

  DOI：

  10.1016/j.ejmech.2010.07.012

文献信息

• Design, synthesis and pro-apoptotic antitumour properties of indole-based 3,5-disubstituted oxadiazoles
  作者：Noha I. Ziedan、Fabio Stefanelli、Stefano Fogli、Andrew D. Westwell

  DOI：10.1016/j.ejmech.2010.07.012

  日期：2010.10

  A series of new indole-based 3,5-disubstituted 1,2,4-oxadiazoles has been designed and synthesised as potential pro-apoptotic antitumour agents, via the base-catalysed condensation reaction between substituted amidoximes and indole esters. Evaluation of antiproliferative activity against the human cancer cell lines COLO 320 (colorectal) and MIA PACA-2 (pancreatic) revealed IC50 values in the low micromolar range. Selected compounds were able to trigger apoptosis in sensitive cell lines, for example via activation of caspase-3/7, demonstrating that indole-based oxadiazoles possess in vitro antitumour and pro-apoptotic activity. (C) 2010 Elsevier Masson SAS All rights reserved.