methyl (E)-3-[4-amino-3-(methylamino)phenyl]prop-2-enoate | 735287-07-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: methyl (E)-3-[4-amino-3-(methylamino)phenyl]prop-2-enoate
• CAS: 735287-07-7
• 化学式: C₁₁H₁₄N₂O₂
• 分子量: 206.244
• InChiKey: UVNRSTOUDXWWPH-GQCTYLIASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  64.4
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl (E)-3-[4-amino-3-(methylamino)phenyl]prop-2-enoate 在 水 、 三乙胺 、 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 、 sodium hydroxide 作用下， 以 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 4.0h， 生成 (E)-3-[3-methyl-2-[1-[(9-methylspiro[7,8-dihydro-6H-carbazole-5,1'-cyclohexane]-2-carbonyl)amino]cyclobutyl]benzimidazol-5-yl]prop-2-enoic acid
  参考文献：
  名称：

  Conformation-Based Restrictions and Scaffold Replacements in the Design of Hepatitis C Virus Polymerase Inhibitors: Discovery of Deleobuvir (BI 207127)

  摘要：

  Conformational restrictions of flexible torsion angles were used to guide the identification of new chemotypes of HCV NS5B inhibitors. Sites for rigidification were based on an acquired conformational understanding of compound binding requirements and the roles of substituents in the free and bound states. Chemical bioisosteres of amide bonds were explored to improve cell-based potency. Examples are shown, including the design concept that led to the discovery of the phase III clinical candidate deleobuvir (BI 207127). The structure-based strategies employed have general utility in drug design.

  DOI：

  10.1021/jm4011862
• 作为产物：
  描述：

  2,4-二氯硝基苯 在 tris-(dibenzylideneacetone)dipalladium(0) 、 sodium dithionite 、 三叔丁基膦 、 N-甲基二环己基胺 、 potassium carbonate 、 三乙胺 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 乙醇 、 水 为溶剂， 反应 100.0h， 生成 methyl (E)-3-[4-amino-3-(methylamino)phenyl]prop-2-enoate
  参考文献：
  名称：

  Conformation-Based Restrictions and Scaffold Replacements in the Design of Hepatitis C Virus Polymerase Inhibitors: Discovery of Deleobuvir (BI 207127)

  摘要：

  Conformational restrictions of flexible torsion angles were used to guide the identification of new chemotypes of HCV NS5B inhibitors. Sites for rigidification were based on an acquired conformational understanding of compound binding requirements and the roles of substituents in the free and bound states. Chemical bioisosteres of amide bonds were explored to improve cell-based potency. Examples are shown, including the design concept that led to the discovery of the phase III clinical candidate deleobuvir (BI 207127). The structure-based strategies employed have general utility in drug design.

  DOI：

  10.1021/jm4011862

文献信息

• Conformation-Based Restrictions and Scaffold Replacements in the Design of Hepatitis C Virus Polymerase Inhibitors: Discovery of Deleobuvir (BI 207127)
  作者：Steven R. LaPlante、Michael Bös、Christian Brochu、Catherine Chabot、René Coulombe、James R. Gillard、Araz Jakalian、Martin Poirier、Jean Rancourt、Timothy Stammers、Bounkham Thavonekham、Pierre L. Beaulieu、George Kukolj、Youla S. Tsantrizos

  DOI：10.1021/jm4011862

  日期：2014.3.13

  Conformational restrictions of flexible torsion angles were used to guide the identification of new chemotypes of HCV NS5B inhibitors. Sites for rigidification were based on an acquired conformational understanding of compound binding requirements and the roles of substituents in the free and bound states. Chemical bioisosteres of amide bonds were explored to improve cell-based potency. Examples are shown, including the design concept that led to the discovery of the phase III clinical candidate deleobuvir (BI 207127). The structure-based strategies employed have general utility in drug design.