2-(Methylamino)-1-(naphthalen-1-yl)ethan-1-ol | 1242161-63-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-(Methylamino)-1-(naphthalen-1-yl)ethan-1-ol
• 英文别名: 2-(methylamino)-1-naphthalen-1-ylethanol
• CAS: 1242161-63-2
• 化学式: C₁₃H₁₅NO
• 分子量: 201.268
• InChiKey: CPSMZZCHIVFDQF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  32.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(Methylamino)-1-(naphthalen-1-yl)ethan-1-ol 在 溶剂黄146 、 sodium nitrite 作用下， 以 水 为溶剂， 生成 N-(2-hydroxy-2-naphthalen-1-ylethyl)-N-methylnitrous amide
  参考文献：
  名称：

  Synthesis, in Vitro Activity, and Three-Dimensional Quantitative Structure−Activity Relationship of Novel Hydrazine Inhibitors of Human Vascular Adhesion Protein-1

  摘要：

  Vascular adhesion protein-1 (VAP-1) belongs to the semicarbazide-sensitive amine oxidases (SSAOs) that convert amines into aldehydes. SSAOs are distinct from the mammalian monoamine oxidases (MAOs), but their substrate specificities are partly overlapping. VAP-1 has been proposed as a target for anti-inflammatory drug therapy because of its role in leukocyte adhesion to endothelium. Here, we describe the synthesis and in vitro activities of novel series of VAP-1 selective inhibitors. In addition, the molecular dynamics simulations performed for VAP-1 reveal that the movements of Met211, Ser496, and especially Leu469 can enlarge the ligand-binding pocket, allowing larger ligands than those seen in the crystal structures to bind. Combining the data from molecular dynamics simulations, docking, and in vitro measurements, the three-dimensional quantitative structure-activity relationship (3D QSAR) models for VAP-1 (q(LOO)(2): 0.636; r(2:) 0.828) and MAOs (q(LOO)(2): 0.749, r(2): 0.840) were built and employed in the development of selective VAP-1 inhibitors.

  DOI：

  10.1021/jm100337z