2-amino-4,5,N-trimethoxy-N-methylbenzamide | 926888-02-0

• 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: 2-amino-4,5,N-trimethoxy-N-methylbenzamide
• 英文别名: 2-amino-N,4,5-trimethoxy-N-methylbenzamide
• CAS: 926888-02-0
• 化学式: C₁₁H₁₆N₂O₄
• mdl: MFCD12095379
• 分子量: 240.259
• InChiKey: NCRZEYSDTJCHOF-UHFFFAOYSA-N

物化性质

• 沸点：
  452.6±45.0 °C(predicted)
• 密度：
  1.193±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.363
• 拓扑面积：
  74
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-amino-4,5,N-trimethoxy-N-methylbenzamide 在 N-甲基吗啉 、 正丁基锂 、 氨 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 为溶剂， 反应 37.0h， 生成 (7,8-dimethoxy-2-oxo-5-phenyl-2,3-dihydro-1H-benzo[e][1,4]diazepin-3-yl)carbamic acid benzyl ester
  参考文献：
  名称：

  1,4-Benzodiazepines as Inhibitors of Respiratory Syncytial Virus

  摘要：

  Respiratory syncytial virus (RSV) is the cause of one-fifth of all lower respiratory tract infections worldwide and is increasingly being recognized as a serious threat to patient groups with poorly functioning immune systems. Our approach to finding a novel inhibitor of this virus was to screen a 20 000-member diverse library in a whole cell XTT assay. Parallel assays were carried out in the absence of virus in order to quantify any associated cell toxicity. This identified 100 compounds with IC50's less than 50 mu M. A-33903 (18), a 1,4-benzodiazepine analogue, was chosen as the starting point for lead optimization. This molecule was moderately active and demonstrated good pharmacokinetic properties. The most potent compounds identified from this work were A-58568 (47), A-58569 (44), and A-62066 (46), where modifications to the aromatic substitution enhanced potency, and A-58175 (42), where the amide linker was modified.

  DOI：

  10.1021/jm051185t
• 作为产物：
  描述：

  2-氨基-4,5-二甲氧基苯甲酸 在 三乙胺 作用下， 以 四氢呋喃 、 乙醇 、 水 为溶剂， 反应 21.17h， 生成 2-amino-4,5,N-trimethoxy-N-methylbenzamide
  参考文献：
  名称：

  1,4-Benzodiazepines as Inhibitors of Respiratory Syncytial Virus

  摘要：

  Respiratory syncytial virus (RSV) is the cause of one-fifth of all lower respiratory tract infections worldwide and is increasingly being recognized as a serious threat to patient groups with poorly functioning immune systems. Our approach to finding a novel inhibitor of this virus was to screen a 20 000-member diverse library in a whole cell XTT assay. Parallel assays were carried out in the absence of virus in order to quantify any associated cell toxicity. This identified 100 compounds with IC50's less than 50 mu M. A-33903 (18), a 1,4-benzodiazepine analogue, was chosen as the starting point for lead optimization. This molecule was moderately active and demonstrated good pharmacokinetic properties. The most potent compounds identified from this work were A-58568 (47), A-58569 (44), and A-62066 (46), where modifications to the aromatic substitution enhanced potency, and A-58175 (42), where the amide linker was modified.

  DOI：

  10.1021/jm051185t

文献信息

• Catalytic Asymmetric Synthesis of Atropisomeric Quinolines through the Friedländer Reaction
  作者：Junlin Wan、Hongxin Liu、Yunjun Lan、Xinhua Li、Xingena Hu、Juan Li、Hong-Ping Xiao、Jun Jiang

  DOI：10.1055/s-0039-1690228

  日期：2019.12

  catalyzed atroposelective Friedlander reaction was developed in which acetylacetone and a variety of 2′-substituted 2-aminobenzophenones were successfully employed to give optically active biaryl quinolines in good yields and with high enantioselectivities.

  开发了一种磷酸催化的阻转选择性 Friedlander 反应，其中成功地使用乙酰丙酮和各种 2'-取代的 2-氨基二苯甲酮以良好的收率和高对映选择性得到具有旋光活性的联芳基喹啉。
• 1,4-Benzodiazepines as Inhibitors of Respiratory Syncytial Virus
  作者：Malcolm C. Carter、Dagmar G. Alber、Robert C. Baxter、Sian K. Bithell、Jo Budworth、Ann Chubb、G. Stuart Cockerill、Verity C. L. Dowdell、Elisa A. Henderson、Sally J. Keegan、Richard D. Kelsey、Michael J. Lockyer、Jeremy N. Stables、Lara J. Wilson、Kenneth L. Powell

  DOI：10.1021/jm051185t

  日期：2006.4.1

  Respiratory syncytial virus (RSV) is the cause of one-fifth of all lower respiratory tract infections worldwide and is increasingly being recognized as a serious threat to patient groups with poorly functioning immune systems. Our approach to finding a novel inhibitor of this virus was to screen a 20 000-member diverse library in a whole cell XTT assay. Parallel assays were carried out in the absence of virus in order to quantify any associated cell toxicity. This identified 100 compounds with IC50's less than 50 mu M. A-33903 (18), a 1,4-benzodiazepine analogue, was chosen as the starting point for lead optimization. This molecule was moderately active and demonstrated good pharmacokinetic properties. The most potent compounds identified from this work were A-58568 (47), A-58569 (44), and A-62066 (46), where modifications to the aromatic substitution enhanced potency, and A-58175 (42), where the amide linker was modified.