N-(2-羟基-2-苯基乙基)-N-甲基亚硝酰胺 | 36972-73-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: N-(2-羟基-2-苯基乙基)-N-甲基亚硝酰胺
• 英文名称: (2-hydroxy-2-phenylethyl)methylnitrosamine
• 英文别名: 2--1-phenyl-aethan-1-ol；2-(N-Nitrosomethylamino)-1-phenyl-1-ethanol；2-(N-Nitrosomethylamino)-1-phenylethanol；2-(N-Nitro-methylamino)-1-phenyl-aethan-1-ol；N-(2-hydroxy-2-phenylethyl)-N-methylnitrous amide
• CAS: 36972-73-3；72656-46-3
• 化学式: C₉H₁₂N₂O₂
• 分子量: 180.206
• InChiKey: DVQKLVCSCYPICN-UHFFFAOYSA-N

物化性质

• 沸点：
  380.6±35.0 °C(Predicted)
• 密度：
  1.13±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  52.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-(2-羟基-2-苯基乙基)-N-甲基亚硝酰胺 以25%的产率得到
  参考文献：
  名称：

  SOAI K.; MUKAIYAMA T., BULL. CHEM. SOC. JAP., 1979, 52. NO 11, 3371-3376

  摘要：

  DOI：
• 作为产物：
  描述：

  α-(甲氨甲基)苯甲醇 在 溶剂黄146 、 sodium nitrite 作用下， 以 水 为溶剂， 生成 N-(2-羟基-2-苯基乙基)-N-甲基亚硝酰胺
  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

文献信息

• Seebach,D.; Enders,D., Chemische Berichte, 1975, vol. 108, p. 1293 - 1320
  作者：Seebach,D.、Enders,D.

  DOI：——

  日期：——
• Renger,B. et al., Chemische Berichte, 1978, vol. 111, p. 2630 - 2645
  作者：Renger,B. et al.

  DOI：——

  日期：——
• Base-induced fragmentation of .beta.-hydroxy nitrosamines
  作者：R. N. Loeppky、W. A. McKinley、L. G. Hazlitt、J. R. Outram

  DOI：10.1021/jo00146a003

  日期：1982.12
• Synthesis, in Vitro Activity, and Three-Dimensional Quantitative Structure−Activity Relationship of Novel Hydrazine Inhibitors of Human Vascular Adhesion Protein-1
  作者：Elisa M. Nurminen、Marjo Pihlavisto、László Lázár、Zsolt Szakonyi、Ulla Pentikäinen、Ferenc Fülöp、Olli T. Pentikäinen

  DOI：10.1021/jm100337z

  日期：2010.9.9

  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.
• SOAI K.; MUKAIYAMA T., BULL. CHEM. SOC. JAP., 1979, 52. NO 11, 3371-3376
  作者：SOAI K.、 MUKAIYAMA T.

  DOI：——

  日期：——