N1-(2-methoxybenzyl)-2-oxoacetamide | 494846-99-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: N1-(2-methoxybenzyl)-2-oxoacetamide
• 英文别名: N-[(2-methoxyphenyl)methyl]-2-oxoacetamide
• CAS: 494846-99-0
• 化学式: C₁₀H₁₁NO₃
• 分子量: 193.202
• InChiKey: GCZQXINPWGIILV-UHFFFAOYSA-N

物化性质

• 密度：
  1.163±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-氨基-1-苯基丙烷-1-醇 、 N1-(2-methoxybenzyl)-2-oxoacetamide 在 4-甲基苯磺酸吡啶 作用下， 以 苯 为溶剂， 反应 4.0h， 以38%的产率得到N2-(2-methoxybenzyl)-6-phenyl-1,3-oxazinane-2-carboxamide
  参考文献：
  名称：

  Metal-organic compounds: a new approach for drug discovery

  摘要：

  The use of metal-organic complexes is a potentially fruitful approach for the development of novel enzyme inhibitors. They hold the attractive promise of forming stronger attachments with the target by combining the co-ordination ability of metals with the unique stereoelectronic properties of the ligand. We demonstrated that this approach can be successfully used to inhibit the protease of the human immunodeficiency virus (type 1). Several ligands bearing substituents designed to interact with the catalytic site of the enzyme when complexed to Cu2+ were synthesised. The inhibition pattern of the resulting copper(II) complexes was analysed. We showed that the copper(II) complex of N1-(4-methyl-2-pyridyl)-2,3,6-trimethoxybenzamide (0) interacts with the active site of the enzyme leading to competitive inhibition. On the other hand, N2-pyridine-amide ligands and oxazinane carboxamide ligand were found to be poor chelators of the cupric ion under the enzymatic assay conditions. In these cases, the observed inhibition was attributed to released cupric ions which react with cysteine residues on the surface of the protease. While unchelated metal cations are not likely to be useful agents, metal chelates such as C1 should be considered as promising lead compounds for the development of targeted drugs. (C) 2002 Elsevier Science Inc. All rights reserved.

  DOI：

  10.1016/s0006-2952(02)00918-8
• 作为产物：
  描述：

  Acetamide, N-[(2-methoxyphenyl)methyl]-2,2-bis[(1-methylethyl)thio]- 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 水 、 乙腈 为溶剂， 反应 0.25h， 以63%的产率得到N1-(2-methoxybenzyl)-2-oxoacetamide
  参考文献：
  名称：

  Metal-organic compounds: a new approach for drug discovery

  摘要：

  The use of metal-organic complexes is a potentially fruitful approach for the development of novel enzyme inhibitors. They hold the attractive promise of forming stronger attachments with the target by combining the co-ordination ability of metals with the unique stereoelectronic properties of the ligand. We demonstrated that this approach can be successfully used to inhibit the protease of the human immunodeficiency virus (type 1). Several ligands bearing substituents designed to interact with the catalytic site of the enzyme when complexed to Cu2+ were synthesised. The inhibition pattern of the resulting copper(II) complexes was analysed. We showed that the copper(II) complex of N1-(4-methyl-2-pyridyl)-2,3,6-trimethoxybenzamide (0) interacts with the active site of the enzyme leading to competitive inhibition. On the other hand, N2-pyridine-amide ligands and oxazinane carboxamide ligand were found to be poor chelators of the cupric ion under the enzymatic assay conditions. In these cases, the observed inhibition was attributed to released cupric ions which react with cysteine residues on the surface of the protease. While unchelated metal cations are not likely to be useful agents, metal chelates such as C1 should be considered as promising lead compounds for the development of targeted drugs. (C) 2002 Elsevier Science Inc. All rights reserved.

  DOI：

  10.1016/s0006-2952(02)00918-8

文献信息

• Inhibitors de serine proteases, especially of the NS3 protease of the hepatitis C virus
  申请人：VERTEX PHARMACEUTICALS INCORPORATED

  公开号：EP2409985A2

  公开（公告）日：2012-01-25

  The present invention relates to compounds, methods and pharmaceutical compositions for inhibiting proteases, particularly serine proteases, and more particularly HCV NS3 proteases. The compounds, and the compositions and methods that utilize them, can be used, either alone or in combination to inhibit viruses, particularly HCV virus.

  本发明涉及用于抑制蛋白酶，特别是丝氨酸蛋白酶，尤其是 HCV NS3 蛋白酶的化合物、方法和药物组合物。这些化合物以及利用它们的组合物和方法可单独或联合用于抑制病毒，特别是 HCV 病毒。
• Metal-organic compounds: a new approach for drug discovery
  作者：Florence Lebon、Nicole Boggetto、Marie Ledecq、François Durant、Zohra Benatallah、Sames Sicsic、René Lapouyade、Olivier Kahn、Ange Mouithys-Mickalad、Ginette Deby-Dupont、Michèle Reboud-Ravaux

  DOI：10.1016/s0006-2952(02)00918-8

  日期：2002.5

  The use of metal-organic complexes is a potentially fruitful approach for the development of novel enzyme inhibitors. They hold the attractive promise of forming stronger attachments with the target by combining the co-ordination ability of metals with the unique stereoelectronic properties of the ligand. We demonstrated that this approach can be successfully used to inhibit the protease of the human immunodeficiency virus (type 1). Several ligands bearing substituents designed to interact with the catalytic site of the enzyme when complexed to Cu2+ were synthesised. The inhibition pattern of the resulting copper(II) complexes was analysed. We showed that the copper(II) complex of N1-(4-methyl-2-pyridyl)-2,3,6-trimethoxybenzamide (0) interacts with the active site of the enzyme leading to competitive inhibition. On the other hand, N2-pyridine-amide ligands and oxazinane carboxamide ligand were found to be poor chelators of the cupric ion under the enzymatic assay conditions. In these cases, the observed inhibition was attributed to released cupric ions which react with cysteine residues on the surface of the protease. While unchelated metal cations are not likely to be useful agents, metal chelates such as C1 should be considered as promising lead compounds for the development of targeted drugs. (C) 2002 Elsevier Science Inc. All rights reserved.