(E)-2-cyano-3-[4-(dimethylamino)phenyl]-2-propenamide | 97006-42-3

• 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: (E)-2-cyano-3-[4-(dimethylamino)phenyl]-2-propenamide
• 英文别名: (E)-2-cyano-3-[4-(dimethylamino)phenyl]acrylamide；2-[4-(dimethylamino)benzylidene]-2-cyanoacetamide；2-cyano-3-(N,N-dimethylaminophenyl)-2-propenamide；2-cyano-3-[4-(dimethylamino)phenyl]propenamide；p-N,N-(dimethylamino)benzylidenecyanoacetamide；2-cyano-3t-(4-dimethylamino-phenyl)-acrylic acid amide；alpha-Cyano-p-(dimethylamino)cinnamamide；(E)-2-cyano-3-[4-(dimethylamino)phenyl]prop-2-enamide
• CAS: 97006-42-3
• 化学式: C₁₂H₁₃N₃O
• 分子量: 215.255
• InChiKey: TVPUSDGUXXMGMH-JXMROGBWSA-N

物化性质

• 熔点：
  197 °C
• 沸点：
  469.5±45.0 °C(Predicted)
• 密度：
  1.203±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  70.1
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-2-cyano-3-[4-(dimethylamino)phenyl]-2-propenamide 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 以61%的产率得到2-cyano-3-[4-(dimethylamino)phenyl]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：

  ((4-(二甲基氨基)苯基)亚甲基)甲烷-1,1-二甲腈 在 sodium acetate 作用下， 以 溶剂黄146 为溶剂， 反应 50.0h， 以47%的产率得到(E)-2-cyano-3-[4-(dimethylamino)phenyl]-2-propenamide
  参考文献：
  名称：

  Mishriky, Nawal; Ibrahim; Girgis, Pharmazie, 2000, vol. 55, # 4, p. 269 - 272

  摘要：

  DOI：

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。
• Tetra‐<i>n</i>‐butylammonium Hydroxide (TBAH)–Catalyzed Knoevenagel Condensation: A Facile Synthesis of α‐Cyanoacrylates, α‐Cyanoacrylonitriles, and α‐Cyanoacrylamides
  作者：Saeed Balalaie、Morteza Bararjanian

  DOI：10.1080/00397910500385258

  日期：2006.3.1

  Abstract Tetra‐n‐butylammonium hydroxide (TBAH) has been utilized as a novel and efficient catalyst for the Knoevenagel condensation of aldehydes with acidic methylene compounds such as methyl‐ and ethylcyanoacetate, malononitrile, and cyanoacetamide to afford substituted olefins.

  摘要 四正丁基氢氧化铵 (TBAH) 已被用作一种新型有效的催化剂，用于醛与酸性亚甲基化合物（如氰基乙酸甲酯和乙酯、丙二腈和氰基乙酰胺）的 Knoevenagel 缩合反应，得到取代的烯烃。
• Some cyano-amides and dicyano-glutaconimides derived from pyridine aldehydes
  作者：J. S. A. Brunskill

  DOI：10.1039/p19720002946

  日期：——

  2-Cyano-3-pyridylacrylamides, 2-cyano-3-pyridylpropionamides, and salts of 3,5-dicyano-6-hydroxy-4-pyridyl-2-pyridones have been prepared from four pyridine aldehydes and tested for pharmacological and antimicrobial activity. Spectra–structure correlations include evidence that in the acrylamides the carbamoyl and pyridyl groups are trans.

  由四个吡啶醛制备了2-氰基-3-吡啶基丙烯酰胺，2-氰基-3-吡啶基丙酰胺和3,5-二氰基-6-羟基-4-吡啶基-2-吡啶酮的盐，并对其药理和抗菌活性进行了测试。 。光谱结构的相关性包括证据表明，在丙烯酰胺中，氨基甲酰基和吡啶基是反式的。
• A study of some reactions of the intermediate isolated from the NN-dimethylaniline–tetracyanoethylene reaction
  作者：P. G. Farrell、R. K. Wojtowski

  DOI：10.1039/j39700001390

  日期：——

  It was previously suggested that the intermediate isolated from the NN-dimethylaniline–tetracyanoethylene reaction was zwitterionic. Synthetic and spectroscopic studies on this intermediate reported here indicate that a neutral substituted ethane structure is the correct one. The compounds formed by hydrolysis of the intermediate by acid and by base are described.

  以前曾有人提出，从NN-二甲基苯胺-四氰基乙烯反应中分离出的中间体是两性离子。此处报道的对该中间体的合成和光谱研究表明，中性取代的乙烷结构是正确的。描述了通过中间体被酸和碱水解形成的化合物。
• [EN] METHODS OF DETECTING NEUROLOGICAL DISORDERS VIA BINDING TO PHOSPHORYLATED TAU PROTEIN<br/>[FR] MÉTHODES DE DÉTECTION DE TROUBLES NEUROLOGIQUES PAR LIAISON À UNE PROTÉINE TAU PHOSPHORYLÉE
  申请人：SARRAF STELLA

  公开号：WO2021055639A1

  公开（公告）日：2021-03-25

  Provided herein are methods and compositions for determining whether a patient suffers from a neurological disease or disorder is provided, comprising detecting the presence of a phosphorylated tau protein in a tissue of the patient, wherein the detecting comprises contacting the phosphorylated tau protein with a compound described herein.

  本文提供了一种确定患者是否患有神经系统疾病或紊乱的方法和组合物，包括检测患者组织中磷酸化tau蛋白的存在，其中检测包括将磷酸化tau蛋白与本文描述的化合物接触。