2-Cyano-N-(3-methoxy-benzyl)-acetamide | 566926-09-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2-Cyano-N-(3-methoxy-benzyl)-acetamide
• 英文别名: 2-cyano-N-(3-methoxybenzyl)acetamide；2-cyano-N-[(3-methoxyphenyl)methyl]acetamide
• CAS: 566926-09-8
• 化学式: C₁₁H₁₂N₂O₂
• 分子量: 204.228
• InChiKey: YRUROVCSGZJLIT-UHFFFAOYSA-N

物化性质

• 沸点：
  459.1±35.0 °C(Predicted)
• 密度：
  1.143±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  62.1
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 危险性防范说明：
  P261,P264,P270,P271,P280,P301+P312,P302+P352,P304+P340,P305+P351+P338,P330,P332+P313,P337+P313,P362,P403+P233,P405,P501
• 危险性描述：
  H302,H312,H315,H319,H332,H335

反应信息

• 作为反应物：
  描述：

  2-Cyano-N-(3-methoxy-benzyl)-acetamide 、 2,3-dichloro-quinoxaline-6-carboxylic acid 3-dimethylamino-propylamide 在 potassium tert-butylate 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 生成 3-chloro-2-[1-cyano-2-[(3-methoxyphenyl)methylamino]-2-oxoethyl]-N-[3-(dimethylamino)propyl]quinoxaline-6-carboxamide
  参考文献：
  名称：

  Discovery and structure–activity relationships of small molecules that block the human immunoglobulin G–human neonatal Fc receptor (hIgG–hFcRn) protein–protein interaction

  摘要：

  The neonatal Fc receptor, FcRn, prolongs the half-life of IgG in the serum and represents a potential therapeutic target for the treatment of autoimmune disease. Small molecules that block the protein-protein interactions of human IgG-human FcRn may lower pathogenic autoantibodies and provide effective treatment. A novel class of quinoxalines has been discovered as antagonists of the IgG:FcRn protein-protein interaction through optimization of a hit derived from a virtual ligand-based screen. (c) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.01.014
• 作为产物：
  描述：

  3-甲氧基苄胺 、 氰乙酸甲酯 生成 2-Cyano-N-(3-methoxy-benzyl)-acetamide
  参考文献：
  名称：

  Tyrphostin-like compounds with ubiquitin modulatory activity as possible therapeutic agents for multiple myeloma

  摘要：

  With the goal of developing small molecules as novel regulators of signal transduction and apoptosis, a series of tyrphostin-like compounds were synthesized and screened for their activity against MM-1 (multiple myeloma) cells and other cell lines representing this malignancy. Synthesis was completed in solution-phase initially and then adopted to solid-phase for generating a more diverse set of compounds. A positive correlation was noted between compounds capable of inducing apoptosis and their modulation of protein ubiquitination. Further analysis suggested that ubiquitin modulation occurs through inhibition of cellular deubiquitinase activity. Bulky groups on the sidechain near the alpha,beta-unsaturated ketone caused a complete loss of activity, whereas cyclization on the opposite side was tolerated. Theoretical calculations at the B3LYP/LACV3P** level were completed on each molecule, and the resulting molecular orbitals and Fukui reactivity values for C(beta) carbon were utilized in developing a model to explain the compound activity. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.09.057

文献信息

• Modulators of LXR
  申请人：——

  公开号：US20030181420A1

  公开（公告）日：2003-09-25

  Compounds, compositions and methods for modulating the activity of nuclear receptors are provided. In particular, heterocyclic compounds are provided for modulating the activity of nuclear receptors, including liver X receptor (LXR) and orphan nuclear receptors. In certain embodiments, the compounds are N-substituted pyridones.

  提供了用于调节核受体活性的化合物、组合物和方法。具体来说，提供了用于调节核受体活性的杂环化合物，包括肝X受体（LXR）和孤儿核受体。在某些实施方式中，这些化合物是N-取代吡啶酮。
• US7998986B2
  申请人：——

  公开号：US7998986B2

  公开（公告）日：2011-08-16
• Tyrphostin-like compounds with ubiquitin modulatory activity as possible therapeutic agents for multiple myeloma
  作者：Zhenghong Peng、Ashutosh Pal、Dongmei Han、Shimei Wang、David Maxwell、Alexander Levitzki、Moshe Talpaz、Nicholas J. Donato、William Bornmann

  DOI：10.1016/j.bmc.2011.09.057

  日期：2011.12

  With the goal of developing small molecules as novel regulators of signal transduction and apoptosis, a series of tyrphostin-like compounds were synthesized and screened for their activity against MM-1 (multiple myeloma) cells and other cell lines representing this malignancy. Synthesis was completed in solution-phase initially and then adopted to solid-phase for generating a more diverse set of compounds. A positive correlation was noted between compounds capable of inducing apoptosis and their modulation of protein ubiquitination. Further analysis suggested that ubiquitin modulation occurs through inhibition of cellular deubiquitinase activity. Bulky groups on the sidechain near the alpha,beta-unsaturated ketone caused a complete loss of activity, whereas cyclization on the opposite side was tolerated. Theoretical calculations at the B3LYP/LACV3P** level were completed on each molecule, and the resulting molecular orbitals and Fukui reactivity values for C(beta) carbon were utilized in developing a model to explain the compound activity. (C) 2011 Elsevier Ltd. All rights reserved.
• Discovery and structure–activity relationships of small molecules that block the human immunoglobulin G–human neonatal Fc receptor (hIgG–hFcRn) protein–protein interaction
  作者：Zhaolin Wang、Cara Fraley、Adam R. Mezo

  DOI：10.1016/j.bmcl.2013.01.014

  日期：2013.3

  The neonatal Fc receptor, FcRn, prolongs the half-life of IgG in the serum and represents a potential therapeutic target for the treatment of autoimmune disease. Small molecules that block the protein-protein interactions of human IgG-human FcRn may lower pathogenic autoantibodies and provide effective treatment. A novel class of quinoxalines has been discovered as antagonists of the IgG:FcRn protein-protein interaction through optimization of a hit derived from a virtual ligand-based screen. (c) 2013 Elsevier Ltd. All rights reserved.