ethyl 5-acetyl-2-ethyl-6-oxo-1,6-dihydropyridine-3-carboxylate | 154020-52-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: ethyl 5-acetyl-2-ethyl-6-oxo-1,6-dihydropyridine-3-carboxylate
• 英文别名: ethyl 5-acetyl-2-ethyl-6-oxo-1H-pyridine-3-carboxylate
• CAS: 154020-52-7
• 化学式: C₁₂H₁₅NO₄
• 分子量: 237.255
• InChiKey: CCNIIDDGMMVFPO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  72.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl 5-acetyl-2-ethyl-6-oxo-1,6-dihydropyridine-3-carboxylate 在 氢氧化钾 作用下， 以 乙醇 为溶剂， 反应 24.0h， 以82%的产率得到5-Acetyl-2-ethyl-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid
  参考文献：
  名称：

  Synthesis and cardiotonic activity of esters of 2-substituted 5-acetyl-1,6-dihydro-6-oxo-3-pyridinecarboxylic acids

  摘要：

  The synthesis of ethyl or methyl esters of 2-substituted 5-acetyl-1,6-dihydro-6-oxo-3-pyridinecarboxylic acids 2a-d, f and 5 by reaction of sodium acetoacetamide with ethyl or methyl 2-dimethylaminomethylene-3-oxoalkanoates and ethyl 2-ethoxymethylene-4,4,4-trifluoro-3-oxobutanoate, respectively, has been described. These esters routinely gave the corresponding carboxylic acids by alkaline hydrolysis followed by acidification. As milrinone analogues, the above compounds were tested on contractile activity and frequency rate of spontaneously beating atria and on contractile activity of electrically-driven left atrium from reserpine-treated guinea pigs. Among the tested compounds, ethyl 5-acetyl-1,6-dihydro-6-oxo-2-phenyl-3-pyridinecarboxylate was found to be more potent and more effective than milrinone as a positive inotropic agent, while only marginally affecting the frequency rate.

  DOI：

  10.1016/0223-5234(93)90037-f
• 作为产物：
  描述：

  乙酰乙酰胺 、 ethyl 2-((dimethylamino)methylene)-3-oxopentanoate 在 sodium hydride 作用下， 以 四氢呋喃 、 mineral oil 为溶剂， 反应 0.5h， 生成 ethyl 5-acetyl-2-ethyl-6-oxo-1,6-dihydropyridine-3-carboxylate
  参考文献：
  名称：

  Pyrid-2-one derivatives and methods of use

  摘要：

  所选化合物对于治疗疾病，如细胞增殖或凋亡介导的疾病，具有有效性。该发明涵盖了新颖的化合物、类似物、前药和其药学上可接受的衍生物，以及用于预防和治疗涉及中风、癌症等疾病和其他疾病或病况的药物组合物和方法。该主题发明还涉及制备此类化合物的方法，以及在这些过程中有用的中间体。

  公开号：

  US20040147561A1

文献信息

• Pyrid-2-one derivatives and methods of use
  申请人：——

  公开号：US20040147561A1

  公开（公告）日：2004-07-29

  Selected compounds are effective for treatment of diseases, such as cell proliferation or apoptosis mediated diseases. The invention encompasses novel compounds, analogs, prodrugs and pharmaceutically acceptable derivatives thereof, pharmaceutical compositions and methods for prophylaxis and treatment of diseases and other maladies or conditions involving stroke, cancer and the like. The subject invention also relates to processes for making such compounds as well as to intermediates useful in such processes.

  所选化合物对于治疗疾病，如细胞增殖或凋亡介导的疾病，具有有效性。该发明涵盖了新颖的化合物、类似物、前药和其药学上可接受的衍生物，以及用于预防和治疗涉及中风、癌症等疾病和其他疾病或病况的药物组合物和方法。该主题发明还涉及制备此类化合物的方法，以及在这些过程中有用的中间体。
• 2-OXOPYRIDIN-3-YL THIA(DI)AZOLE DERIVATIVES FOR USE IN THE TREATMENT OF CELL PROLIFERATION AND APOPTOSIS RELATED DISEASES
  申请人：AMGEN INC.

  公开号：EP1575947A1

  公开（公告）日：2005-09-21
• [EN] 2-OXOPYRIDIN-3-YL THIA (DI) AZOLE DERIVATES FOR USE IN THE TREATMENT OF CELL PROLIFERATION AND APOPTOSIS RELATED DISEASES<br/>[FR] DERIVES DE PYRIDE-2-ONE ET PROCEDES D'UTILISATION
  申请人：AMGEN INC

  公开号：WO2004060890A1

  公开（公告）日：2004-07-22

  Compounds of formula I are effective for treatment of diseases, such as cell proliferation or apoptosis mediated diseases. The invention encompasses novel compounds, pharmaceutical compositions and methods for prophylaxis and treatment of diseases and other maladies or conditions involvong stroke, cancer and the like.
• Design and synthesis of 6-oxo-1,6-dihydropyridines as CDK5 inhibitors
  作者：Matthew R. Kaller、Wenge Zhong、Charles Henley、Ella Magal、Thomas Nguyen、David Powers、Robert M. Rzasa、Weiya Wang、Xiaoling Xiong、Mark H. Norman

  DOI：10.1016/j.bmcl.2009.10.027

  日期：2009.12

  Cyclin-dependent kinase 5 (CDK5) is a serine-threonine protein kinase that plays a significant role in neuronal development. In association with p25, CDK5 abnormally phosphorylates a number of cellular targets involved in neurodegenerative disorders. Using active site homology and previous structure-activity relationships, a new series of potent CDK5 inhibitors was designed. This report describes the optimization of 6-oxo-1,6-dihydropyridines as CDK5 inhibitors. (C) 2009 Elsevier Ltd. All rights reserved.
• Synthesis and cardiotonic activity of esters of 2-substituted 5-acetyl-1,6-dihydro-6-oxo-3-pyridinecarboxylic acids
  作者：L Mosti、P Schenone、M Iester、P Dorigo、RM Gaion、D Fraccarollo

  DOI：10.1016/0223-5234(93)90037-f

  日期：1993.1

  The synthesis of ethyl or methyl esters of 2-substituted 5-acetyl-1,6-dihydro-6-oxo-3-pyridinecarboxylic acids 2a-d, f and 5 by reaction of sodium acetoacetamide with ethyl or methyl 2-dimethylaminomethylene-3-oxoalkanoates and ethyl 2-ethoxymethylene-4,4,4-trifluoro-3-oxobutanoate, respectively, has been described. These esters routinely gave the corresponding carboxylic acids by alkaline hydrolysis followed by acidification. As milrinone analogues, the above compounds were tested on contractile activity and frequency rate of spontaneously beating atria and on contractile activity of electrically-driven left atrium from reserpine-treated guinea pigs. Among the tested compounds, ethyl 5-acetyl-1,6-dihydro-6-oxo-2-phenyl-3-pyridinecarboxylate was found to be more potent and more effective than milrinone as a positive inotropic agent, while only marginally affecting the frequency rate.