6-methyl-N-(2-nitrophenyl)-N'-(3,4,5-trimethoxyphenyl)-1,3,5-triazine-2,4-diamine | 1374227-41-4

• 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: 6-methyl-N-(2-nitrophenyl)-N'-(3,4,5-trimethoxyphenyl)-1,3,5-triazine-2,4-diamine
• 英文别名: 6-methyl-4-N-(2-nitrophenyl)-2-N-(3,4,5-trimethoxyphenyl)-1,3,5-triazine-2,4-diamine
• CAS: 1374227-41-4
• 化学式: C₁₉H₂₀N₆O₅
• 分子量: 412.405
• InChiKey: UEWLDKAMSDNQDM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  30
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  136
• 氢给体数：
  2
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  6-methyl-N-(2-nitrophenyl)-N'-(3,4,5-trimethoxyphenyl)-1,3,5-triazine-2,4-diamine 在 吡啶 、 palladium 10% on activated carbon 、 2-氨基-n-乙基苯甲酰胺 作用下， 以 甲醇 为溶剂， 反应 5.0h， 生成 N-(2-(4-methyl-6-(3,4,5-trimethoxyphnylamino)-1,3,5-triazin-2-ylamino)phenyl)methanesulfonamide
  参考文献：
  名称：

  Synthesis of novel diarylamino-1,3,5-triazine derivatives as FAK inhibitors with anti-angiogenic activity

  摘要：

  We report herein the synthesis of novel diarylamino-1,3,5-triazine derivatives as FAR (focal adhesion kinase) inhibitors and the evaluation of their anti-angiogenic activity on HUVEC cells. Generally, the effects of these compounds on endothelial cells could be correlated with their kinase inhibitory activity. The most efficient compounds displayed inhibition of viability against HUVEC cells in the micromolar range, as observed with TAE-226, which was designed by Novartis Pharma AG. X-ray crystallographic analysis of the co-crystal structure for compound 34 revealed that the mode of interaction with the FAR kinase domain is highly similar to that observed in the complex of TAE-226. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.06.038
• 作为产物：
  描述：

  3,4,5-trimethoxyphenylbiguanide 在 sodium methylate 、 palladium diacetate 、 caesium carbonate 、 4,5-双二苯基膦-9,9-二甲基氧杂蒽 作用下， 以 四氢呋喃 、 1,4-二氧六环 为溶剂， 反应 0.33h， 生成 6-methyl-N-(2-nitrophenyl)-N'-(3,4,5-trimethoxyphenyl)-1,3,5-triazine-2,4-diamine
  参考文献：
  名称：

  Synthesis of novel diarylamino-1,3,5-triazine derivatives as FAK inhibitors with anti-angiogenic activity

  摘要：

  We report herein the synthesis of novel diarylamino-1,3,5-triazine derivatives as FAR (focal adhesion kinase) inhibitors and the evaluation of their anti-angiogenic activity on HUVEC cells. Generally, the effects of these compounds on endothelial cells could be correlated with their kinase inhibitory activity. The most efficient compounds displayed inhibition of viability against HUVEC cells in the micromolar range, as observed with TAE-226, which was designed by Novartis Pharma AG. X-ray crystallographic analysis of the co-crystal structure for compound 34 revealed that the mode of interaction with the FAR kinase domain is highly similar to that observed in the complex of TAE-226. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.06.038

文献信息

• High yielding microwave-assisted synthesis of tri-substituted 1,3,5-triazines using Pd-catalyzed aryl and heteroarylamination
  作者：Pascal Dao、Christiane Garbay、Huixiong Chen

  DOI：10.1016/j.tet.2012.03.041

  日期：2012.5

  A rapid and efficient Pd-catalyzed aryl and heteroarylamination under microwave irradiation has been developed for various tri-substituted triazines that can serve as versatile building blocks for both supramolecular and medicinal chemistry research. Particularly valuable features of this method included the short reaction time, good yield, and convenient operation. (C) 2012 Elsevier Ltd. All rights reserved.