2-[[4-[(2-methylquinolin-4-yl)methoxy]benzoyl]amino]acetic acid | 681283-89-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-[[4-[(2-methylquinolin-4-yl)methoxy]benzoyl]amino]acetic acid
• CAS: 681283-89-6
• 化学式: C₂₀H₁₈N₂O₄
• 分子量: 350.374
• InChiKey: UDJKQWDRTFZMBE-UHFFFAOYSA-N

物化性质

• 沸点：
  636.7±55.0 °C(Predicted)
• 密度：
  1.301±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.94
• 重原子数：
  26.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  88.52
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  2-[[4-[(2-methylquinolin-4-yl)methoxy]benzoyl]amino]acetic acid 在 N-甲基吗啉 、 sodium hydroxide 、 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 4-((2-methylquinolin-4-yl)methoxy)-N-((5-thioxo-4,5-dihydro-1H-1,2,4-triazol-3-yl)methyl)benzamide
  参考文献：
  名称：

  Synthesis and structure–activity relationship of a novel, non-hydroxamate series of TNF-α converting enzyme inhibitors

  摘要：

  A novel series of TNF-alpha converting enzyme (TACE) inhibitors which are non-hydroxamate have been discovered. These compounds use a triazolethione moiety as the zinc binding ligand and exhibit IC(50) values from 1.5 to 100 nM in a porcine TACE assay. They also have excellent selectivities over other MMPs.(c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.05.100
• 作为产物：
  描述：

  4-[(2-methyl-4-quinolinyl)methoxy]benzoyl chloride 、 聚甘氨酸 生成 2-[[4-[(2-methylquinolin-4-yl)methoxy]benzoyl]amino]acetic acid
  参考文献：
  名称：

  Hydantoins, triazolones, and imidazolones as selective non-hydroxamate inhibitors of tumor necrosis factor-α converting enzyme (TACE)

  摘要：

  We have discovered selective and potent inhibitors of TACE that replace the common hydroxamate zinc binding group with a hydantoin, triazolone, and imidazolone heterocycle. These novel heterocyclic inhibitors of a zinc metalloprotease were designed using a pharmacophore model that we previously described while developing hydantoin and pyrimidinetrione (barbiturate) inhibitors of TACE. The potency and binding orientation of these inhibitors is discussed and they are modeled into the X-ray crystal structure of TACE and compared to hydroxamate and earlier hydantoin TACE inhibitors which share the same 4-[(2-methyl-4-quinolinyl)methoxy]benzoyl Pl' group. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.02.076