2-{4-amino-6-[4-(4-nitrophenyl)piperazin-1-yl]-1,3,5-triazin-2-yl}acetonitrile | 886968-54-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: 2-{4-amino-6-[4-(4-nitrophenyl)piperazin-1-yl]-1,3,5-triazin-2-yl}acetonitrile
• 英文别名: 2-[4-Amino-6-[4-(4-nitrophenyl)piperazin-1-yl]-1,3,5-triazin-2-yl]acetonitrile
• CAS: 886968-54-3
• 化学式: C₁₅H₁₆N₈O₂
• 分子量: 340.344
• InChiKey: AGQXTECYIJBIPH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  141
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  2-{4-amino-6-[4-(4-nitrophenyl)piperazin-1-yl]-1,3,5-triazin-2-yl}acetonitrile 、 N,N-二甲基-4-亚硝基苯胺 在 氢氧化钾 作用下， 以 乙醇 、 水 为溶剂， 反应 12.5h， 以60%的产率得到2-{4-amino-6-[4-(4-nitrophenyl)piperazin-1-yl]-1,3,5-triazin-2-yl}-2-{[4-(dimethylamino)phenyl]imino}acetonitrile
  参考文献：
  名称：

  Synthesis, structure and anticancer activity of novel 2,4-diamino-1,3,5-triazine derivatives

  摘要：

  A series of 2-(4,6-diamino-1,3,5-triazin-2-yl)-2-{[4-(dimethylamino)-phenyl]imino}acetonitriles 19-27 have been synthesized by the reaction of 2-(4-amino-6-alkylamino-1,3,5-triazin-2-yl)acetonitriles 10-15 with p-nitrosodimethylaniline. Unexpectedly, a similar reaction of acetonitriles 10, 14, 15, 17 and 18 with nitrosobenzene led to the formation of 4,6-diamino-N-phenyl-1,3,5-triazine-2-carboxamides 28-32. The in vitro antitumor activity of the compounds obtained has been tested and 2-[4-Amino-6-(4-phenylpiperazin-1-yl)-1,3,5-triazin-2-yl]-2{[4-(dimethylamino)phenyl]imino}acetonitrile (19) having remarkable activity against melanoma MALME-3 M cell line (GI(50) = 3.3 x 10(-8) M, TGI = 1.1 x 10(-6) M) is a leading candidate for further development. (c) 2005 Elsevier SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2005.10.013
• 作为产物：
  描述：

  1-(4-nitrophenyl)piperazine hydrochloride 以 甲醇 、 正丁醇 为溶剂， 反应 11.0h， 生成 2-{4-amino-6-[4-(4-nitrophenyl)piperazin-1-yl]-1,3,5-triazin-2-yl}acetonitrile
  参考文献：
  名称：

  Synthesis, structure and anticancer activity of novel 2,4-diamino-1,3,5-triazine derivatives

  摘要：

  A series of 2-(4,6-diamino-1,3,5-triazin-2-yl)-2-{[4-(dimethylamino)-phenyl]imino}acetonitriles 19-27 have been synthesized by the reaction of 2-(4-amino-6-alkylamino-1,3,5-triazin-2-yl)acetonitriles 10-15 with p-nitrosodimethylaniline. Unexpectedly, a similar reaction of acetonitriles 10, 14, 15, 17 and 18 with nitrosobenzene led to the formation of 4,6-diamino-N-phenyl-1,3,5-triazine-2-carboxamides 28-32. The in vitro antitumor activity of the compounds obtained has been tested and 2-[4-Amino-6-(4-phenylpiperazin-1-yl)-1,3,5-triazin-2-yl]-2{[4-(dimethylamino)phenyl]imino}acetonitrile (19) having remarkable activity against melanoma MALME-3 M cell line (GI(50) = 3.3 x 10(-8) M, TGI = 1.1 x 10(-6) M) is a leading candidate for further development. (c) 2005 Elsevier SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2005.10.013

文献信息

• Synthesis, structure and anticancer activity of novel 2,4-diamino-1,3,5-triazine derivatives
  作者：F. Sączewski、A. Bułakowska、P. Bednarski、R. Grunert

  DOI：10.1016/j.ejmech.2005.10.013

  日期：2006.2

  A series of 2-(4,6-diamino-1,3,5-triazin-2-yl)-2-[4-(dimethylamino)-phenyl]imino}acetonitriles 19-27 have been synthesized by the reaction of 2-(4-amino-6-alkylamino-1,3,5-triazin-2-yl)acetonitriles 10-15 with p-nitrosodimethylaniline. Unexpectedly, a similar reaction of acetonitriles 10, 14, 15, 17 and 18 with nitrosobenzene led to the formation of 4,6-diamino-N-phenyl-1,3,5-triazine-2-carboxamides 28-32. The in vitro antitumor activity of the compounds obtained has been tested and 2-[4-Amino-6-(4-phenylpiperazin-1-yl)-1,3,5-triazin-2-yl]-2[4-(dimethylamino)phenyl]imino}acetonitrile (19) having remarkable activity against melanoma MALME-3 M cell line (GI(50) = 3.3 x 10(-8) M, TGI = 1.1 x 10(-6) M) is a leading candidate for further development. (c) 2005 Elsevier SAS. All rights reserved.