N-(p-nitrocinnamoyl)imidazole | 351027-13-9

• 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: N-(p-nitrocinnamoyl)imidazole
• 英文别名: (E)-1-imidazol-1-yl-3-(4-nitrophenyl)prop-2-en-1-one
• CAS: 351027-13-9
• 化学式: C₁₂H₉N₃O₃
• 分子量: 243.222
• InChiKey: AQIIFAXVPBDIDV-ZZXKWVIFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  80.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-(p-nitrocinnamoyl)imidazole 在 盐酸羟胺 作用下， 以 四氢呋喃 为溶剂， 以146 mg的产率得到trans-N-hydroxy-3-(4-nitro-phenyl)-acrylamide
  参考文献：
  名称：

  Hydroxamic Acids Block Replication of Hepatitis C Virus

  摘要：

  Intrigued by the role of protein acetylation in hepatitis C virus (HCV) replication, we tested known histone deacetylase (HDAC) inhibitors and a focused library of structurally simple hydroxamic acids for inhibition of a HCV subgenomic replicon. While known HDAC inhibitors with varied inhibitory profiles proved to be either relatively toxic or ineffective, structureactivity relationship (SAR) studies on cinnamic hydroxamic acid and benzo[b]thiophen-2-hydroxamic acid gave rise to compounds 22 and 53, which showed potent and selective anti-HCV activity and therefore are promising starting points for further structural optimization and mechanistic studies.

  DOI：

  10.1021/jm501330g
• 作为产物：
  描述：

  对硝基肉桂酸 、 N,N'-羰基二咪唑 以 四氢呋喃 为溶剂， 反应 1.33h， 生成 N-(p-nitrocinnamoyl)imidazole
  参考文献：
  名称：

  Hydroxamic Acids Block Replication of Hepatitis C Virus

  摘要：

  Intrigued by the role of protein acetylation in hepatitis C virus (HCV) replication, we tested known histone deacetylase (HDAC) inhibitors and a focused library of structurally simple hydroxamic acids for inhibition of a HCV subgenomic replicon. While known HDAC inhibitors with varied inhibitory profiles proved to be either relatively toxic or ineffective, structureactivity relationship (SAR) studies on cinnamic hydroxamic acid and benzo[b]thiophen-2-hydroxamic acid gave rise to compounds 22 and 53, which showed potent and selective anti-HCV activity and therefore are promising starting points for further structural optimization and mechanistic studies.

  DOI：

  10.1021/jm501330g

文献信息

• Cinnamoyl Inhibitors of Tissue Transglutaminase
  作者：Christophe Pardin、Joelle N. Pelletier、William D. Lubell、Jeffrey W. Keillor

  DOI：10.1021/jo8004843

  日期：2008.8.1

  inhibitors of guinea pig liver transglutaminase. The most effective inhibitors evaluated can be sorted into two subclasses: substituted cinnamoyl benzotriazolyl amides and the 3-(substituted cinnamoyl)pyridines, referred to more commonly as azachalcones. Kinetic evaluation of both of these subclasses revealed that they display reversible inhibition and are competitive with acyl donor TGase substrates at IC50

  转谷氨酰胺酶（TGase）催化某些蛋白质的分子间交联，而组织TGase（TG2）参与多种生物过程。不受调节的高TGase活性与几种生理疾病有关，但几乎没有可逆的TG2抑制剂报道。在这里，我们报告了一系列新型反式的合成-肉桂酰胺衍生物，被发现是豚鼠肝脏转谷氨酰胺酶的有效抑制剂。评估的最有效的抑制剂可分为两类：取代的肉桂酰基苯并三唑基酰胺和3-（取代的肉桂酰基）吡啶，通常被称为氮杂环庚烷。对这两个亚类的动力学评估表明，它们在IC 50值低至18μM时显示可逆的抑制作用，并且与酰基供体TGase底物竞争。对这些抑制剂系列中的结构活性关系的分析允许鉴定潜在的重要结合相互作用。对一些最有效抑制剂的进一步测试表明它们对TG2的选择性以及其进一步开发的潜力。
• The Michael Reaction of N-Cinnamoylazoles with Phenols. A Simple Synthesis of 4-Arylchroman-2-ones and 1-Arylbenzo[f]chroman-3-ones
  作者：Giovanna Speranza、Carlo F. Morelli、Paolo Manitto

  DOI：10.1055/s-2000-6233

  日期：——

  4-Arylchroman-2-ones 3 and 1-arylbenzo[f]chroman-3-ones 6 have been prepared in moderate to good yields by reaction of dihydric or trihydric phenols with p-substituted N-cinnamoylazoles in dichloromethane under reflux in the presence of DBU.

  4-芳基色满-2-酮3和1-芳基苯并[f]色满-3-酮6已通过将二羟基或三羟基苯酚与对位取代的N-肉桂酰基吡唑在二氯甲烷中回流并在DBU存在下反应，以中等至良好的产率制备。
• Barbry; Champagne, Journal of Chemical Research - Part S, 2001, # 2, p. 78 - 79
  作者：Barbry、Champagne

  DOI：——

  日期：——
• Hydroxamic Acids Block Replication of Hepatitis C Virus
  作者：Teng Ai、Yanli Xu、Li Qiu、Robert J. Geraghty、Liqiang Chen

  DOI：10.1021/jm501330g

  日期：2015.1.22

  Intrigued by the role of protein acetylation in hepatitis C virus (HCV) replication, we tested known histone deacetylase (HDAC) inhibitors and a focused library of structurally simple hydroxamic acids for inhibition of a HCV subgenomic replicon. While known HDAC inhibitors with varied inhibitory profiles proved to be either relatively toxic or ineffective, structureactivity relationship (SAR) studies on cinnamic hydroxamic acid and benzo[b]thiophen-2-hydroxamic acid gave rise to compounds 22 and 53, which showed potent and selective anti-HCV activity and therefore are promising starting points for further structural optimization and mechanistic studies.