N-(5-azidopentyl)-5-[(6-bromo-1H-indol-3-yl)methyl]-1,2,4-oxadiazol-3-amine | 1374238-55-7

• 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-(5-azidopentyl)-5-[(6-bromo-1H-indol-3-yl)methyl]-1,2,4-oxadiazol-3-amine
• CAS: 1374238-55-7
• 化学式: C₁₆H₁₈BrN₇O
• 分子量: 404.269
• InChiKey: LTTKRZRUHACJAN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  25
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  81.1
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N-(5-azidopentyl)-5-[(6-bromo-1H-indol-3-yl)methyl]-1,2,4-oxadiazol-3-amine 在 甲酸铵 、 silver nitrate 、 三乙胺 、 锌 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 14.0h， 生成 N-[5-[[[[(1,1-dimethylethoxy)carbonyl]amino][[(1,1-dimethylethoxy)carbonyl]imino]methyl]amino]pentyl]-5-[(6-bromo-1H-indol-3-yl)methyl]-1,2,4-oxadiazol-3-amine
  参考文献：
  名称：

  Synthesis of Phidianidines A and B

  摘要：

  Reaction of a substituted indole-3-acetyl chloride with N-5-azidopentyl-N'-hydroxyguanidine generated a substituted 3-(5-azidopentylamino)-5-((indol-3-yl)methyl)-1,2,4-oxadiazole. Reduction of the azide with zinc and ammonium formate afforded the amine, which was elaborated to the guanidine, completing short and efficient syntheses of the cytotoxic natural products phidianidines A and B in 19% overall yield by a convergent route that will make analogues readily available for biological evaluation. Initial screening in the NCI 60 cell line at 10(-5) M indicated that the bromine on the indole is necessary for activity and that the amine precursor to phidianidine A is more potent than phidianidine A.

  DOI：

  10.1021/jo300449n
• 作为产物：
  描述：

  6-溴吲哚-3-乙酸 在 草酰氯 、 三乙胺 、 N,N-二甲基甲酰胺 作用下， 以 二氯甲烷 为溶剂， 反应 5.5h， 生成 N-(5-azidopentyl)-5-[(6-bromo-1H-indol-3-yl)methyl]-1,2,4-oxadiazol-3-amine
  参考文献：
  名称：

  Synthesis of Phidianidines A and B

  摘要：

  Reaction of a substituted indole-3-acetyl chloride with N-5-azidopentyl-N'-hydroxyguanidine generated a substituted 3-(5-azidopentylamino)-5-((indol-3-yl)methyl)-1,2,4-oxadiazole. Reduction of the azide with zinc and ammonium formate afforded the amine, which was elaborated to the guanidine, completing short and efficient syntheses of the cytotoxic natural products phidianidines A and B in 19% overall yield by a convergent route that will make analogues readily available for biological evaluation. Initial screening in the NCI 60 cell line at 10(-5) M indicated that the bromine on the indole is necessary for activity and that the amine precursor to phidianidine A is more potent than phidianidine A.

  DOI：

  10.1021/jo300449n

文献信息

• Synthesis of Phidianidines A and B
  作者：Hong-Yu Lin、Barry B. Snider

  DOI：10.1021/jo300449n

  日期：2012.5.18

  Reaction of a substituted indole-3-acetyl chloride with N-5-azidopentyl-N'-hydroxyguanidine generated a substituted 3-(5-azidopentylamino)-5-((indol-3-yl)methyl)-1,2,4-oxadiazole. Reduction of the azide with zinc and ammonium formate afforded the amine, which was elaborated to the guanidine, completing short and efficient syntheses of the cytotoxic natural products phidianidines A and B in 19% overall yield by a convergent route that will make analogues readily available for biological evaluation. Initial screening in the NCI 60 cell line at 10(-5) M indicated that the bromine on the indole is necessary for activity and that the amine precursor to phidianidine A is more potent than phidianidine A.