2-cyano-2-(2,3-dihydro-1H-inden-1-ylidene)acetamide | 33017-14-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: 2-cyano-2-(2,3-dihydro-1H-inden-1-ylidene)acetamide
• 英文别名: (E)-1-Indanylidencyanacetamid；Indan-1-ylidencyanoacetamid；alpha-[1-Indanylidene]cyanoacetamide；(2E)-2-cyano-2-(2,3-dihydroinden-1-ylidene)acetamide
• CAS: 33017-14-0
• 化学式: C₁₂H₁₀N₂O
• 分子量: 198.224
• InChiKey: AWEZTDJFBVXUSK-ZHACJKMWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  66.9
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-茚酮 、 2-cyano-2-(2,3-dihydro-1H-inden-1-ylidene)acetamide 生成 3'-oxospiro[1,2-dihydroindene-3,1'-4,9-dihydro-2H-indeno[2,1-c]pyridine]-4'-carboxamide
  参考文献：
  名称：

  EWEISS N. F.; MOUSTOFA A. H.; SHAMS N. A., REV. ROUM. CHIM., 1979, 23, NO 11-12, 1485-1489

  摘要：

  DOI：
• 作为产物：
  描述：

  1-茚酮 、 氰乙酰胺 在 N-甲基哌嗪 、 ammonium acetate 作用下， 以 乙醇 为溶剂， 生成 2-cyano-2-(2,3-dihydro-1H-inden-1-ylidene)acetamide
  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