N-(2-fluorophenyl)-5,6,7-trimethoxyquinazoline-4-amine | 1173284-42-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: N-(2-fluorophenyl)-5,6,7-trimethoxyquinazoline-4-amine
• 英文别名: N-(2-fluorophenyl)-5,6,7-trimethoxyquinazolin-4-amine
• CAS: 1173284-42-8
• 化学式: C₁₇H₁₆FN₃O₃
• 分子量: 329.331
• InChiKey: XHWPTLTXWVDNMB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  65.5
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  methyl 2,3,4-trimethoxy-6-nitrobenzoate 在 palladium 10% on activated carbon 、 氢气 、 sodium methylate 、 三乙胺 、 三氯氧磷 作用下， 以 甲醇 、 乙醇 、 N,N-二甲基甲酰胺 、 异丙醇 、 甲苯 为溶剂， 反应 40.0h， 生成 N-(2-fluorophenyl)-5,6,7-trimethoxyquinazoline-4-amine
  参考文献：
  名称：

  Synthesis and anticancer activities of 5,6,7-trimethoxy-N-phenyl(ethyl)-4-aminoquinazoline derivatives

  摘要：

  A series of 5,6,7-trimethoxy-N-phenyl(ethyl)-4-aminoquinazoline compounds was prepared by microwave irradiation and conventional heating methods. Compounds 6p, 6q, and 6x strongly inhibited extracellular regulated kinase1/2 (ERK1/2) phosphorylation induced by epidermal growth factor (EGF) at 1.28 mu M in PC3 cells. 3-(4,5-Dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide assay showed that all compounds had certain anticancer activities, and the IC50 values of 6x were 6.2 +/- 0.9, 3.2 +/- 0.1, and 3.1 +/- 0.1 mu M against PC3, BGC823, and Bcap37 cells, respectively. Acridine orange/ethidium bromide staining, Hoechst 33258 staining, DNA ladder, and flow cytometry analyses revealed that 6x induced cell apoptosis in PC3 cells, with apoptosis ratios of 11.6% at 1 mu M and 31.8% at 10 mu M after 72 h. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.05.043

文献信息

• Synthesis and anticancer activities of 5,6,7-trimethoxy-N-phenyl(ethyl)-4-aminoquinazoline derivatives
  作者：Ying Zhang、Linhong Jin、Hongmei Xiang、Jian Wu、Peiyi Wang、Deyu Hu、Wei Xue、Song Yang

  DOI：10.1016/j.ejmech.2013.05.043

  日期：2013.8

  A series of 5,6,7-trimethoxy-N-phenyl(ethyl)-4-aminoquinazoline compounds was prepared by microwave irradiation and conventional heating methods. Compounds 6p, 6q, and 6x strongly inhibited extracellular regulated kinase1/2 (ERK1/2) phosphorylation induced by epidermal growth factor (EGF) at 1.28 mu M in PC3 cells. 3-(4,5-Dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide assay showed that all compounds had certain anticancer activities, and the IC50 values of 6x were 6.2 +/- 0.9, 3.2 +/- 0.1, and 3.1 +/- 0.1 mu M against PC3, BGC823, and Bcap37 cells, respectively. Acridine orange/ethidium bromide staining, Hoechst 33258 staining, DNA ladder, and flow cytometry analyses revealed that 6x induced cell apoptosis in PC3 cells, with apoptosis ratios of 11.6% at 1 mu M and 31.8% at 10 mu M after 72 h. (C) 2013 Elsevier Masson SAS. All rights reserved.