2-cyano-3-quinolin-4-yl-acrylic acid ethyl ester | 177616-95-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 2-cyano-3-quinolin-4-yl-acrylic acid ethyl ester
• 英文别名: ethyl 2-cyano-3-(quinolin-4-yl)acrylate；ethyl 2-cyano-3-quinolin-4-ylacrylate；ethyl 2-cyano-3-quinolin-4-ylprop-2-enoate
• CAS: 177616-95-4
• 化学式: C₁₅H₁₂N₂O₂
• mdl: MFCD06210245
• 分子量: 252.272
• InChiKey: NHAQXIGAEKRJQM-UHFFFAOYSA-N

物化性质

• 沸点：
  439.6±35.0 °C(Predicted)
• 密度：
  1.237±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.133
• 拓扑面积：
  63
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-cyano-3-quinolin-4-yl-acrylic acid ethyl ester 、 1-萘基溴化镁, 0.5M IN METHF 以 四氢呋喃 为溶剂， 反应 3.0h， 生成 Ethyl 2-cyano-3-naphthalen-1-yl-3-quinolin-4-ylpropanoate
  参考文献：
  名称：

  Estrogen Receptor Dependent Inhibitors of NF-κB Transcriptional Activation-1 Synthesis and Biological Evaluation of Substituted 2-Cyanopropanoic Acid Derivatives:  Pathway Selective Inhibitors of NF-κB, a Potential Treatment for Rheumatoid Arthritis

  摘要：

  Pathway selective ligands of the estrogen receptor inhibit transcriptional activation of proinflammatory genes mediated by NF kappa B. Substituted 2-cyanopropanoic acid derivatives were developed leading to the discovery of WAY-204688, an orally active, pathway selective, estrogen receptor dependent anti-inflammatory agent. This propanamide was shown to be orally active in preclinical models of inflammatory diseases, such as rheumatoid arthritis, without the proliferative effect associated with traditional, estrogens.

  DOI：

  10.1021/jm701013k
• 作为产物：
  描述：

  4-喹啉甲醛 、 氰乙酸乙酯 在 piperidine, encapsulated in desolvated Mn-MOF (Mn₃(NDC)₃(DMF)₄) 作用下， 以 水 为溶剂， 反应 1.5h， 以97%的产率得到2-cyano-3-quinolin-4-yl-acrylic acid ethyl ester
  参考文献：
  名称：

  [受电子邮件保护]复合材料：Knoevenagel缩合反应的合成，表征和有效催化剂

  摘要：

  我们通过在去溶剂化的Mn-MOF中包裹哌啶合成了新的[受电子邮件保护的]复合材料，并研究了其在Knoevenagel缩合反应中的催化性能。新开发的复合材料可与各种芳族醛相容，并将它们以良好的收率和选择性转化为所需的Knoevenagel缩合产物。此外，复合材料（受电子邮件保护）可重复使用，并且比天然MOF表现出良好的催化活性。

  DOI：

  10.1016/j.tetlet.2017.11.004

文献信息

• [EN] INSULIN-REGULATED AMINOPEPTIDASE (IRAP) INHIBITORS AND USES THEREOF<br/>[FR] INHIBITEURS DE L'AMINOPEPTIDASE RÉGULÉE PAR L'INSULINE (IRAP) ET LEURS APPLICATIONS
  申请人：HOWARD FLOREY INST

  公开号：WO2009065169A1

  公开（公告）日：2009-05-28

  The present invention relates to inhibitors of insulin-regulated aminopeptidase (IRAP) and methods for inhibiting same, as well as compositions comprising said inhibitors. In particular, the inhibitors of the present invention may be useful in therapeutic applications including enhancing memory and learning functions.

  本发明涉及胰岛素调节氨肽酶（IRAP）的抑制剂及其抑制方法，以及包含该抑制剂的组合物。特别是，本发明的抑制剂可能在治疗应用中具有用途，包括增强记忆和学习功能。
• INSULIN-REGULATED AMINOPEPTIDASE (IRAP) INHIBITORS AND USES THEREOF
  申请人：CHAI SIEW YEEN

  公开号：US20120309787A1

  公开（公告）日：2012-12-06

  The present invention relates to inhibitors of insulin-regulated aminopeptidase (IRAP) and methods for inhibiting same, as well as compositions comprising said inhibitors. In particular, the inhibitors of the present invention may be useful in therapeutic applications including enhancing memory and learning functions.

  本发明涉及胰岛素调节氨肽酶（IRAP）的抑制剂及其抑制方法，以及包含该抑制剂的组合物。特别地，本发明的抑制剂可用于治疗应用，包括增强记忆和学习功能。
• Estrogen Receptor Dependent Inhibitors of NF-κB Transcriptional Activation-1 Synthesis and Biological Evaluation of Substituted 2-Cyanopropanoic Acid Derivatives:  Pathway Selective Inhibitors of NF-κB, a Potential Treatment for Rheumatoid Arthritis
  作者：Thomas J. Caggiano、Antony Brazzale、Douglas M. Ho、Christina M. Kraml、Eugene Trybulski、Christopher C. Chadwick、Sue Chippari、Lisa Borges-Marcucci、Amy Eckert、James C. Keith、Thomas Kenney、Douglas C. Harnish

  DOI：10.1021/jm701013k

  日期：2007.11.1

  Pathway selective ligands of the estrogen receptor inhibit transcriptional activation of proinflammatory genes mediated by NF kappa B. Substituted 2-cyanopropanoic acid derivatives were developed leading to the discovery of WAY-204688, an orally active, pathway selective, estrogen receptor dependent anti-inflammatory agent. This propanamide was shown to be orally active in preclinical models of inflammatory diseases, such as rheumatoid arthritis, without the proliferative effect associated with traditional, estrogens.
• Mn-MOF@Pi composite: synthesis, characterisation and an efficient catalyst for the Knoevenagel condensation reaction
  作者：Darsi Rambabu、Mohammad Ashraf、Pooja、Ankush Gupta、Abhimanew Dhir

  DOI：10.1016/j.tetlet.2017.11.004

  日期：2017.12

  [email protected] composite by encapsulation of piperidine in desolvated Mn-MOF and investigated its catalytic performance in Knoevenagel condensation reaction. The newly developed composite is compatible with various aromatic aldehydes and converting them to the desired Knoevenagel condensation products in good yields and selectivity. Furthermore, composite [email protected] is reusable and shows good catalytic

  我们通过在去溶剂化的Mn-MOF中包裹哌啶合成了新的[受电子邮件保护的]复合材料，并研究了其在Knoevenagel缩合反应中的催化性能。新开发的复合材料可与各种芳族醛相容，并将它们以良好的收率和选择性转化为所需的Knoevenagel缩合产物。此外，复合材料（受电子邮件保护）可重复使用，并且比天然MOF表现出良好的催化活性。