4-amino-6-(morpholin-4-yl)-N-phenyl-1,3,5-triazine-2-carboxamide | 7537-63-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-amino-6-(morpholin-4-yl)-N-phenyl-1,3,5-triazine-2-carboxamide
• 英文别名: 4-Amino-6-morpholino-s-triazin-carbonsaeure-(2)-anilid；4-amino-6-morpholin-4-yl-[1,3,5]triazine-2-carboxylic acid anilide；2-Amino-4-morpholino-6-phenylcarbamoyl-1,3,5-triazine；4-amino-6-morpholin-4-yl-N-phenyl-1,3,5-triazine-2-carboxamide
• CAS: 7537-63-5
• 化学式: C₁₄H₁₆N₆O₂
• 分子量: 300.32
• InChiKey: CMMRTAJJNFZZTF-UHFFFAOYSA-N

物化性质

• 熔点：
  >350 °C(Solv: N,N-dimethylformamide (68-12-2); water (7732-18-5))
• 密度：
  1.406±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  106
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  吗啉胍 在 sodium carbonate 作用下， 以 甲醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 生成 4-amino-6-(morpholin-4-yl)-N-phenyl-1,3,5-triazine-2-carboxamide
  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

• Furukawa,M. et al., Chemical and pharmaceutical bulletin, 1972, vol. 20, # 3, p. 611 - 613
  作者：Furukawa,M. et al.

  DOI：——

  日期：——
• 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.

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