methyl 2,3,4-trimethoxy-6-nitrobenzoate | 1752-00-7

• 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: methyl 2,3,4-trimethoxy-6-nitrobenzoate
• 英文别名: Methyl benzoate, 6-nitro-2,3,4-methoxy-
• CAS: 1752-00-7
• 化学式: C₁₁H₁₃NO₇
• 分子量: 271.227
• InChiKey: MEUXGIGBLQIBSC-UHFFFAOYSA-N

物化性质

• 熔点：
  78-79 °C
• 沸点：
  421.0±40.0 °C(Predicted)
• 密度：
  1.284±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  99.8
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  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-(3-chlorophenyl)-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
• 作为产物：
  描述：

  methyl 2,3,4-trimethoxybenzoate 在 硝酸 、 溶剂黄146 作用下， 生成 methyl 2,3,4-trimethoxy-6-nitrobenzoate
  参考文献：
  名称：

  Pollak; Goldstein, Justus Liebigs Annalen der Chemie, 1907, vol. 351, p. 168

  摘要：

  DOI：

文献信息

• Synthesis and anticancer activities of 4-(4-substituted piperazin)-5,6,7-trialkoxy quinazoline derivatives
  作者：Ying Zhang、Yin-Jiu Huang、Hong-Mei Xiang、Pei-Yi Wang、De-Yu Hu、Wei Xue、Bao-An Song、Song Yang

  DOI：10.1016/j.ejmech.2014.03.036

  日期：2014.5

  A series of 4-(4-substituted piperazin)-5,6,7-trialkoxy quinazoline was prepared by conventional heating methods. Among these compounds, the crystal structure of compound 10o (CCDC: 916922) was determined by X-ray crystallography. Bioassay results showed that most target compounds had certain inhibition activities against proliferation of tumor cells, and some compounds even had good broad-spectrum

  通过常规加热方法制备了一系列4-（4-取代的哌嗪）-5,6,7-三烷氧基喹唑啉。在这些化合物中，化合物10o（CCDC：916922）的晶体结构通过X射线晶体学测定。生物测定结果表明，大多数目标化合物对肿瘤细胞的增殖具有一定的抑制活性，有些化合物甚至具有良好的广谱抑制活性。乙氧基系列化合物比甲氧基系列化合物对肿瘤细胞具有更高的抑制活性。生物活性测试表明，化合物10s的IC 50值相对于PC3，MGC803，A375和A549细胞分别为1.8、2.8、1.3和2.9μM，远高于商品吉非替尼（分别为7.2、7.6、7.2和9.8μM）。相反，化合物10s对NH3T3的IC 50值非常低，表明对正常细胞的作用很小，这也可以通过乳酸脱氢酶和a啶橙/溴化乙锭染色来证明。细胞构型和细胞周期的分析表明，化合物10s可能通过抑制24 h的细胞增殖而使细胞停留在G 0 / G 1相。复合10s也抑制ERK1
• 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.
• Pollak; Goldstein, Justus Liebigs Annalen der Chemie, 1907, vol. 351, p. 168
  作者：Pollak、Goldstein

  DOI：——

  日期：——