(E)-2-cyano-3-(3-hydroxyphenyl)acrylamide

• 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: (E)-2-cyano-3-(3-hydroxyphenyl)acrylamide
• 英文别名: 2-Cyano-3-(3-hydroxy-phenyl)-acrylamide；(E)-2-cyano-3-(3-hydroxyphenyl)prop-2-enamide
• 化学式: C₁₀H₈N₂O₂
• 分子量: 188.186
• InChiKey: QNEGNWNZPWHAKM-XBXARRHUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  87.1
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  间羟基苯甲醛 、 氰乙酰胺 在 哌啶 作用下， 以 乙醇 为溶剂， 反应 24.0h， 以64%的产率得到(E)-2-cyano-3-(3-hydroxyphenyl)acrylamide
  参考文献：
  名称：

  Bicyclic compounds as ring-constrained inhibitors of protein-tyrosine kinase p56lck

  摘要：

  A study was undertaken to prepare inhibitors of the lymphocyte protein-tyrosine kinase p56lck. Using the known p56lck inhibitor 3,4-dihydroxy-alpha-cyanocinnamamide (4) as a lead compound, bicyclic analogues were designed as conformationally constrained mimetics in which the phenyl ring and vinyl side chain of the cinnamamide are locked into a coplanar orientation. Such planarity was rationalized to be an important determinant for binding within a putative flat, cleftlike catalytic cavity. Bicyclic analogues were prepared using the naphthalene, quinoline, isoquinoline, and 2-iminochromene ring systems and examined for their ability to inhibit autophosphorylation of immunopurified p56lck. The most potent analogues were methyl 7,8-dihydroxyisoquinoline-3-carboxylate (12) (IC50 = 0.2 muM) and 7,8-dihydroxyisoquinoline-3-carboxamide (13) (IC50 = 0.5 muM). Inhibition by 12 was not competitive with respect to ATP. These compounds may represent important new structural motifs for the development of p56lck inhibitors.

  DOI：

  10.1021/jm00056a001

文献信息

• Arylcyanoacrylamides as inhibitors of the Dengue and West Nile virus proteases
  作者：Christoph Nitsche、Christian Steuer、Christian D. Klein

  DOI：10.1016/j.bmc.2011.10.061

  日期：2011.12

  The 3-aryl-2-cyanoacrylamide scaffold was designed as core pharmacophore for inhibitors of the Dengue and West Nile virus serine proteases (NS2B-NS3). A total of 86 analogs was prepared to study the structure-activity relationships in detail. Thereby, it turned out that the electron density of the aryl moiety and the central double bond have a crucial influence on the activity of the compounds, whereas the influence of substituents of the amide residue is less relevant. The para-hydroxy substituted analog was found to be the most potent inhibitor in this series with a K(i)-value of 35.7 mu M at the Dengue and 44.6 mu M at the West Nile virus protease. The aprotinin competition assay demonstrates a direct interaction of the inhibitor molecule with active centre of the Dengue virus protease. The target selectivity was studied in a counterscreen with thrombin and found to be 2.8:1 in favor of DEN protease and 2.3:1 in favor of WNV protease, respectively. (C) 2011 Elsevier Ltd. All rights reserved.
• Burke (Jr) Terrence R., Lim Benjamin, Marquez Victor E., Li Zhen-Hong, Bo+, J. Med. Chem., 36 (1993) N 4, S 425-432
  作者：Burke (Jr) Terrence R., Lim Benjamin, Marquez Victor E., Li Zhen-Hong, Bo+

  DOI：——

  日期：——