(E)-2-cyano-3-(4-(morpholinyl)phenyl)acrylamide | 1044857-46-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 恶嗪烷类
• 英文名称: (E)-2-cyano-3-(4-(morpholinyl)phenyl)acrylamide
• 英文别名: 2-Cyano-3-[4-(4-morpholinyl)phenyl]acrylamide；(E)-2-cyano-3-(4-morpholin-4-ylphenyl)prop-2-enamide
• CAS: 1044857-46-6
• 化学式: C₁₄H₁₅N₃O₂
• 分子量: 257.292
• InChiKey: MRGJWJSTAKYGCH-FMIVXFBMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  79.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (E)-2-cyano-3-(4-(morpholinyl)phenyl)acrylamide 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 以54%的产率得到2-cyano-3-(4-morpholin-4-ylphenyl)propanamide
  参考文献：
  名称：

  Arylcyanoacrylamides as inhibitors of the Dengue and West Nile virus proteases

  摘要：

  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.

  DOI：

  10.1016/j.bmc.2011.10.061
• 作为产物：
  描述：

  吗啉 、 对氟苯甲醛 、 氰乙酰胺 以 乙醇 为溶剂， 反应 0.08h， 以78%的产率得到(E)-2-cyano-3-(4-(morpholinyl)phenyl)acrylamide
  参考文献：
  名称：

  Microwave-assisted three-component Knoevenagel-nucleophilic aromatic substitution reactions

  摘要：

  A powerful microwave-assisted three-component Knoevenagel-nucleophilic aromatic substitution reaction of 4-halobenzaldehydes, cyanoacetatic acid esters/cyanoacetamides, and cyclic secondary amines has been developed. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.05.122

文献信息

• [EN] AMYLOID TARGETING AGENTS AND METHODS OF USING THE SAME<br/>[FR] AGENTS CIBLANT LES AMYLOÏDES ET PROCÉDÉS DE LEUR UTILISATION
  申请人：AMYDIS DIAGNOSTICS

  公开号：WO2015143185A1

  公开（公告）日：2015-09-24

  Provided herein is the design and synthesis of novel molecular rotor fluorophores useful for detection of amyloid or amyloid like proteins. The fluorophores are designed to exhibit enhanced fluorescence emission upon associating with amyloid or amyloid like proteins as compared to unbound compound. Also disclosed herein are the methods for treating of diseases associated with an amyloid or amyloid like proteins.

  本文提供了用于检测淀粉样蛋白或类淀粉样蛋白的新型分子转子荧光团的设计和合成。这些荧光团被设计为与淀粉样蛋白或类淀粉样蛋白结合时，与未结合化合物相比表现出增强的荧光发射。本文还披露了用于治疗与淀粉样蛋白或类淀粉样蛋白相关疾病的方法。
• 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.
• Microwave-assisted three-component Knoevenagel-nucleophilic aromatic substitution reactions
  作者：Hui Xu、Xinhong Yu、Leying Sun、Jing Liu、Wen Fan、Yongjia Shen、Wei Wang

  DOI：10.1016/j.tetlet.2008.05.122

  日期：2008.8

  A powerful microwave-assisted three-component Knoevenagel-nucleophilic aromatic substitution reaction of 4-halobenzaldehydes, cyanoacetatic acid esters/cyanoacetamides, and cyclic secondary amines has been developed. (C) 2008 Elsevier Ltd. All rights reserved.