N-cyano-1H-indole-2-carboxamide | 1263814-48-7

• 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: N-cyano-1H-indole-2-carboxamide
• 英文别名: 1H-indole-2-carbonyl cyanamide
• CAS: 1263814-48-7
• 化学式: C₁₀H₇N₃O
• 分子量: 185.185
• InChiKey: YJJBMFZEENHYSQ-UHFFFAOYSA-N

物化性质

• 密度：
  1.365±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  68.7
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-cyano-1H-indole-2-carboxamide 在 吡啶 、 盐酸羟胺 作用下， 以 乙醇 为溶剂， 反应 17.25h， 生成 3-amino-5-(indol-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：

  1H-吲哚-2-羰酰氯 、 氰胺 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 生成 N-cyano-1H-indole-2-carboxamide
  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

• Ultrasound-Assisted Synthesis of N-Acylcyanamides and N-Acyl-Substituted Imidazolones from Carboxylic Acids by Using Trichloroisocyanuric Acid/Triphenylphosphine
  作者：Wong Phakhodee、Dolnapa Yamano、Mookda Pattarawarapan

  DOI：10.1055/s-0039-1691583

  日期：2020.4

  A convenient ultrasound-assisted one-pot synthesis of N-acylcyanamides starting from readily available carboxylic acids and sodium cyanamide has been developed. Upon activation in the presence of trichloroisocyanuric acid (TCCA) and triphenylphosphine, a range of carboxylic acids was converted into N-acylcyanamides in good to excellent yields within 10 minutes at room temperature without base. Remarkably

  已经开发出一种方便的超声波辅助一锅法合成 N-酰基氰胺，从容易获得的羧酸和氰氨化钠开始。在三氯异氰脲酸 (TCCA) 和三苯基膦存在下活化后，一系列羧酸在室温下 10 分钟内以良好至极好的收率转化为 N-酰基氰胺，无碱。值得注意的是，N-酰基取代的咪唑酮很容易通过原位生成的 N-酰基氰胺的鸟苷化环化获得。