2-氰基-N-（四氢呋喃-2-基甲基）-乙酰胺 | 324546-22-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 四氢呋喃
• 中文名称: 2-氰基-N-（四氢呋喃-2-基甲基）-乙酰胺
• 英文名称: 2-cyano-N-((tetrahydrofuran-2-yl)methyl)acetamide
• 英文别名: 2-cyano-N-(tetrahydrofuran-2-ylmethyl)acetamide；2-cyano-N-(oxolan-2-ylmethyl)acetamide
• CAS: 324546-22-7
• 化学式: C₈H₁₂N₂O₂
• mdl: MFCD00121391
• 分子量: 168.195
• InChiKey: WQPYFXKRRMIJFM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  62.1
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 危险等级：
  IRRITANT
• 海关编码：
  2932190090
• 储存条件：
  室温

反应信息

• 作为反应物：
  描述：

  2-氰基-N-（四氢呋喃-2-基甲基）-乙酰胺 在 盐酸 、 水 、 sodium ethanolate 作用下， 以 乙醇 为溶剂， 反应 11.0h， 生成 2,5-dihydro-N-((tetrahydrofuran-2-yl)methyl)-4,5,5-trimethyl-2-oxofuran-3-carboxamide
  参考文献：
  名称：

  通过后续反应有效合成新丁烯内酯：用于合成原始亚氨基内酯，双亚氨基内酯和双内酯的应用

  摘要：

  根据α-羟基酮的两种策略，我们通过随后的酯化-缩合或加成-缩合反应，开发了二十四种新的亚氨基内酯，双亚氨基内酯和双内酯。描述了双亚氨基内酯的X射线衍射数据，并给出了令人感兴趣的螺旋柱填料。

  DOI：

  10.1016/j.tet.2010.12.062
• 作为产物：
  描述：

  2-四氢糠胺 、 氰乙酸甲酯 以90%的产率得到2-氰基-N-（四氢呋喃-2-基甲基）-乙酰胺
  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

文献信息

• Synthesis of resveratrol acrylamides derivatives and biological evaluation of their anti-proliferative effect on cancer cell lines
  作者：Ban-Feng Ruan、Si-Qi Wang、Xiao-Lin Ge、Ri-Sheng Yao

  DOI：10.2174/15701808113109990057

  日期：2013.11

  A new series of resveratrol acrylamides amine derivatives was designed, synthesized, and evaluated for their anti-proliferative activity against three cancer cell lines including human chronic myelocytic leukemia cell K562, human hepatoma HuH-7 and human lung carcinoma A549. Most of the compounds showed superior activity against three cell lines when compared to parent resveratrol. C13 had the best anti-tumor activity against the HuH-7 cell line and its IC50 was 4.5 μmol/L; C16 had the best anti-tumor activity against the K562 cell line and its IC50 was 2.9 μmol/L; C18 had the best anti-tumor activity against the A549 cell line and its IC50 was 3.8 μmol/L. It could be seen that the activity of the aromatic amine derivatives was better than the fatty amine derivatives by analyzing the experimental data.

  设计、合成并评价了一系列白藜芦醇丙烯酰胺胺衍生物对三种癌细胞株的抗增殖活性，包括人慢性髓细胞白血病细胞K562、人肝癌HuH-7和人肺癌A549。与母体白藜芦醇相比，大多数化合物对三种细胞株表现出更强的活性。C13对HuH-7细胞株具有最佳的抗肿瘤活性，其IC50为4.5 μmol/L; C16对K562细胞株具有最佳的抗肿瘤活性，其IC50为2.9 μmol/L；C18对A549细胞株具有最佳的抗肿瘤活性，其IC50为3.8 μmol/L。通过分析实验数据可以发现，芳香胺衍生物的活性优于脂肪胺衍生物。
• Structure–Activity Relationship of SPOP Inhibitors against Kidney Cancer
  作者：Ze Dong、Zhen Wang、Zhong-Qiang Guo、Shouzhe Gong、Tao Zhang、Jiang Liu、Cheng Luo、Hualiang Jiang、Cai-Guang Yang

  DOI：10.1021/acs.jmedchem.0c00161

  日期：2020.5.14

  Previously, we elucidated that the oncogenic SPOP-signaling pathway in ccRCC could be suppressed by 6b that inhibits SPOP-mediated protein interactions. Herein, we have established a structure-activity relationship for 6b analogues as SPOP inhibitors. Compound 6lc suppresses the viability and inhibits the colony formation of ccRCC cell lines driven by cytoplasmic SPOP, superior to 6b. Compound 6lc binds

  在几乎所有的透明细胞肾细胞癌（ccRCC）中，斑点型POZ蛋白（SPOP）在细胞核中过度表达，并在细胞质中错位，从而导致肾脏肿瘤发生。先前，我们阐明了ccRCC中的致癌SPOP信号通路可能被抑制SPOP介导的蛋白质相互作用的6b所抑制。在这里，我们已经建立了6b类似物作为SPOP抑制剂的构效关系。化合物6lc抑制了活力，并抑制了优于6b的细胞质SPOP驱动的ccRCC细胞系的集落形成。化合物6lc在体外与SPOP蛋白结合，并破坏HEK293T细胞中SPOP与磷酸酶和肌腱蛋白同源物（PTEN）的结合，这引起了可观察到的现象：PTEN泛素化的下降，当ccRCC细胞系以剂量反应方式暴露于6lc时，PTEN和双重特异性磷酸酶7的水平升高，磷酸化AKT和ERK的水平降低。两者合计，化合物6lc是对抗肾肿瘤发生的有效候选物。
• 3-Formylchromones in Guareschi Synthesis of 5-(2-hydroxybenzoyl)-2-pyridones
  作者：Dmitriy M. Volochnyuk、Sergey V. Ryabukhin、Andrey S. Plaskon、Andrey A. Tolmachev

  DOI：10.1055/s-2004-832852

  日期：——

  A set of 5-(2-hydroxybenzoyl)-pyrid-2-ones, which are analogous to cardiotonic drugs such as milrinone, has been prepared in high yield by recyclization of 3-formylchromones with acetic acid amides having at the α-position an electron-withdrawing group. The best reaction conditions were found to be heating in DMF in the presence of Me3SiCl as a promoter and water scavenger.

  一组5-(2-羟基苯甲酰)-吡啶-2-酮的化合物，类似于米利酮等强心药，通过将3-醛基香豆素与在α位具有电子吸引基团的乙酸酰胺进行再环化高产量制备而成。最佳反应条件是将反应体系加热于DMF中，并添加Me3SiCl作为促进剂和脱水剂。
• US3985763A
  申请人：——

  公开号：US3985763A

  公开（公告）日：1976-10-12
• 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.