5-(5-chloroindol-2-yl)-3-(4-chlorophenyl)-1,2,4-oxadiazole | 1253493-65-0

• 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-chloroindol-2-yl)-3-(4-chlorophenyl)-1,2,4-oxadiazole
• 英文别名: 5-(5-chloro-1H-indol-2-yl)-3-(4-chlorophenyl)-1,2,4-oxadiazole
• CAS: 1253493-65-0
• 化学式: C₁₆H₉Cl₂N₃O
• 分子量: 330.173
• InChiKey: RQBNEFDXBOCNBV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  22
• 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：
  54.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-(5-chloroindol-2-yl)-3-(4-chlorophenyl)-1,2,4-oxadiazole 、 碘甲烷 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 8.5h， 以83%的产率得到3-(4-chlorophenyl)-5-(5-chloro-1-methylindol-2-yl)-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
• 作为产物：
  描述：

  5-氯吲哚-2-羧酸乙酯 、 4-氯-N-羟基苯羧酰亚胺 在 sodium ethanolate 作用下， 以 乙醇 为溶剂， 反应 0.5h， 以47%的产率得到5-(5-chloroindol-2-yl)-3-(4-chlorophenyl)-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