N-(5-amino-1-(4-methoxybenzyl)-1H-pyrazol-4-yl)-2-methyl-4-aminobenzamide | 1292281-67-4

• 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: N-(5-amino-1-(4-methoxybenzyl)-1H-pyrazol-4-yl)-2-methyl-4-aminobenzamide
• CAS: 1292281-67-4
• 化学式: C₁₉H₂₁N₅O₂
• 分子量: 351.408
• InChiKey: SVZNFBNSWBEPNE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.67
• 重原子数：
  26.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  108.19
• 氢给体数：
  3.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  5-甲基异恶唑-3-甲酸 、 N-(5-amino-1-(4-methoxybenzyl)-1H-pyrazol-4-yl)-2-methyl-4-aminobenzamide 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 N-(4-(5-amino-1-(4-methoxybenzyl)-1H-pyrazol-4-ylcarbamoyl)-3-methylphenyl)-5-methylisoxazole-3-carboxamide
  参考文献：
  名称：

  Structure based design and syntheses of amino-1H-pyrazole amide derivatives as selective Raf kinase inhibitors in melanoma cells

  摘要：

  The synthesis of a novel series of N-(5-amino-1-(4-methoxybenzyl)-1H-pyrazol-4-yl amide derivatives 6a-o, 7a-s and their antiproliferative activities against A375P melanoma cell line were described. Most compounds showed competitive antiproliferative activities to sorafenib, the reference standard. Among them, N-(5-amino-1-(4-methoxybenzyl)-1H-pyrazol-4-yl)-5-(3-(4-chloro-3-(trifluoromethyl)phenyl)ureido)-2-methylbenzamide 7c exhibited potent activities (GI(50) = 0.27 mu M). Especially, 7c was found to be a potent and selective B-Raf V600E and C-Raf inhibitor (IC50 = 0.26 mu M, IC50 = 0.11 mu M, respectively), showing a possibility as melanoma therapeutics. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.01.067
• 作为产物：
  描述：

  N-(5-amino-1-(4-methoxybenzyl)-1H-pyrazol-4-yl)-2-methyl-4-nitrobenzamide 在 盐酸 、 tin(II) chloride dihdyrate 作用下， 以 乙醇 为溶剂， 反应 1.5h， 生成 N-(5-amino-1-(4-methoxybenzyl)-1H-pyrazol-4-yl)-2-methyl-4-aminobenzamide
  参考文献：
  名称：

  Structure based design and syntheses of amino-1H-pyrazole amide derivatives as selective Raf kinase inhibitors in melanoma cells

  摘要：

  The synthesis of a novel series of N-(5-amino-1-(4-methoxybenzyl)-1H-pyrazol-4-yl amide derivatives 6a-o, 7a-s and their antiproliferative activities against A375P melanoma cell line were described. Most compounds showed competitive antiproliferative activities to sorafenib, the reference standard. Among them, N-(5-amino-1-(4-methoxybenzyl)-1H-pyrazol-4-yl)-5-(3-(4-chloro-3-(trifluoromethyl)phenyl)ureido)-2-methylbenzamide 7c exhibited potent activities (GI(50) = 0.27 mu M). Especially, 7c was found to be a potent and selective B-Raf V600E and C-Raf inhibitor (IC50 = 0.26 mu M, IC50 = 0.11 mu M, respectively), showing a possibility as melanoma therapeutics. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.01.067