3-amino-1-(4-methoxybenzyl)-2-pyridone | 356578-32-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 3-amino-1-(4-methoxybenzyl)-2-pyridone
• 英文别名: 3-Amino-1-[(4-methoxyphenyl)methyl]pyridin-2-one
• CAS: 356578-32-0
• 化学式: C₁₃H₁₄N₂O₂
• 分子量: 230.266
• InChiKey: OYIVQWPLVNWDLW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  55.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-amino-1-(4-methoxybenzyl)-2-pyridone 在 盐酸 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 作用下， 以 1,4-二氧六环 、 二氯甲烷 为溶剂， 反应 19.58h， 生成 3-[2'-(S)-(1'''-naphthylacetyl)amino-3'-(4''-methoxycarbonylmethyl)benzene]propanoylamino-1-(4-methoxybenzyl)-2-pyridone
  参考文献：
  名称：

  Nonpeptidic, Monocharged, Cell Permeable Ligands for the p56lck SH2 Domain

  摘要：

  p561ck is a member of the src family of tyrosine kinases and plays a critical role in the signal transduction events that lead to T cell activation. Ligands for the p561ck SH2 domain have the potential to disrupt the interaction of p561ck with its substrates and derail the signaling cascade that leads to the production of cytokines such as interleukin-2. Starting from the quintuply charged (at physiological pH) phosphorylated tetrapeptide, AcpYEEI, we recently disclosed (J. Med. Chem. 1999, 42, 722 and J. Med. Chem. 1999, 42, 1757) the design of the modified dipeptide 3, which carries just two charges at physiological pH. Here we present the elaboration of 3 to the nonpeptidic, monocharged compound, 9S. This molecule displays good binding affinity for the p561ck SH2 domain (K-d 1 muM) and good cell permeation, and this combination of properties allowed us to demonstrate clear-cut inhibitory effects on a very early event in T cell activation, namely calcium mobilization.

  DOI：

  10.1021/jm000446q
• 作为产物：
  描述：

  ethyl (2E,4E)-5-methoxy-2-nitropenta-2,4-dienoate 在 铁粉 、 氯化铵 、 N,N-二异丙基乙胺 作用下， 以 甲醇 、 水 为溶剂， 反应 2.02h， 生成 3-amino-1-(4-methoxybenzyl)-2-pyridone
  参考文献：
  名称：

  N-取代的3-氨基-2-吡啶酮的合成

  摘要：

  吡啶酮是有机合成中的多功能构件，也是药物发现的特权基序。然而，在吡啶酮氮原子上带有α-叔碳、环丙基或杂环的N-取代2-吡啶酮仍然难以制备。在此，我们描述了从硝基乙酸乙酯和现成的伯胺结构单元有效合成多种 N 取代的 2-吡啶酮，可在大规模和平行的药物化学应用中使用。

  DOI：

  10.1021/acs.orglett.2c02189

文献信息

• [EN] Pyrazolopyrrolidine compounds<br/>[FR] COMPOSÉS PYRAZOLOPYRROLIDINE
  申请人：NOVARTIS AG

  公开号：WO2013080141A1

  公开（公告）日：2013-06-06

  The invention relates to compounds of formula (I) as described herein, pharmaceutical preparations comprising such compounds, uses and methods of use for such compounds in the treatment of a disorder or a disease mediated by the activity of MDM2 and/or MDM4, and combinations comprising such compounds.

  该发明涉及公式（I）所述的化合物，包括这些化合物的药物制剂，以及这些化合物在治疗由MDM2和/或MDM4活性介导的疾病或疾病中的用途和使用方法，以及包含这些化合物的组合物。
• 3-Urea-1-(phenylmethyl)-pyridones as novel, potent, and selective EP3 receptor antagonists
  作者：Yue H. Li、Pei-San Tseng、Karen A. Evans、Jon-Paul Jaworski、Dwight M. Morrow、Harvey E. Fries、Charlene W. Wu、Richard M. Edwards、Jian Jin

  DOI：10.1016/j.bmcl.2010.08.137

  日期：2010.11

  A series of 3-urea-1-(phenylmethyl)-pyridones was discovered as novel EP3 antagonists via high-throughput screening and subsequent optimization. The synthesis, structure-activity relationships, and optimization of the initial hit that resulted in potent and selective EP3 receptor antagonists such as 11g are described. (C) 2010 Elsevier Ltd. All rights reserved.
• PYRAZOLOPYRROLIDINE COMPOUNDS
  申请人：Novartis AG

  公开号：EP2785717A1

  公开（公告）日：2014-10-08
• Nonpeptidic, Monocharged, Cell Permeable Ligands for the p56lck SH2 Domain
  作者：John R. Proudfoot、Rajashehar Betageri、Mario Cardozo、Thomas A. Gilmore、Susan Glynn、Eugene R. Hickey、Scott Jakes、Alisa Kabcenell、Thomas M. Kirrane、Annette K. Tibolla、Susan Lukas、Usha R. Patel、Rajiv Sharma、Mehran Yazdanian、Neil Moss、Pierre L. Beaulieu、Dale R. Cameron、Jean-Marie Ferland、Jean Gauthier、James Gillard、Vida Gorys、Martin Poirier、Jean Rancourt、Dominik Wernic、Montse Llinas-Brunet

  DOI：10.1021/jm000446q

  日期：2001.7.1

  p561ck is a member of the src family of tyrosine kinases and plays a critical role in the signal transduction events that lead to T cell activation. Ligands for the p561ck SH2 domain have the potential to disrupt the interaction of p561ck with its substrates and derail the signaling cascade that leads to the production of cytokines such as interleukin-2. Starting from the quintuply charged (at physiological pH) phosphorylated tetrapeptide, AcpYEEI, we recently disclosed (J. Med. Chem. 1999, 42, 722 and J. Med. Chem. 1999, 42, 1757) the design of the modified dipeptide 3, which carries just two charges at physiological pH. Here we present the elaboration of 3 to the nonpeptidic, monocharged compound, 9S. This molecule displays good binding affinity for the p561ck SH2 domain (K-d 1 muM) and good cell permeation, and this combination of properties allowed us to demonstrate clear-cut inhibitory effects on a very early event in T cell activation, namely calcium mobilization.
• Synthesis of N-Substituted 3-Amino-2-pyridones
  作者：Philippe N. Bolduc、Magnus Pfaffenbach、Vanna D. Blasczak、Steven R. Mathieu、Emily A. Peterson

  DOI：10.1021/acs.orglett.2c02189

  日期：2022.8.26

  building blocks in organic synthesis and a privileged motif in drug discovery. However, N-substituted 2-pyridones bearing an α-tertiary carbon, cyclopropyl, or heterocycle off of the pyridone nitrogen atom remain challenging to prepare. Herein, we describe the efficient synthesis of a large variety of N-substituted 2-pyridones from ethyl nitroacetate and readily available primary amine building blocks

  吡啶酮是有机合成中的多功能构件，也是药物发现的特权基序。然而，在吡啶酮氮原子上带有α-叔碳、环丙基或杂环的N-取代2-吡啶酮仍然难以制备。在此，我们描述了从硝基乙酸乙酯和现成的伯胺结构单元有效合成多种 N 取代的 2-吡啶酮，可在大规模和平行的药物化学应用中使用。