(+/-)-erythro-2-methylamino-1-phenyl-pentanol-(1) | 1422619-11-1

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (+/-)-erythro-2-methylamino-1-phenyl-pentanol-(1)
• 英文别名: (alphaS)-rel-alpha-[(1R)-1-(Methylamino)butyl]-benzenemethanol；(1S,2R)-2-(methylamino)-1-phenylpentan-1-ol
• CAS: 1422619-11-1
• 化学式: C₁₂H₁₉NO
• 分子量: 193.289
• InChiKey: KJHDJPCRJFLIHX-NEPJUHHUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 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：

  (+/-)-erythro-2-methylamino-1-phenyl-pentanol-(1) 在 溶剂黄146 、 sodium nitrite 作用下， 以 水 为溶剂， 生成 N-[(1R,2S)-1-hydroxy-1-phenylpentan-2-yl]-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
• 作为产物：
  描述：

  2-(甲基氨基)-1-苯基戊-1-酮 在 Pd-BaSO₄ 、 高氯酸 、 溶剂黄146 作用下， 生成 (+/-)-erythro-2-methylamino-1-phenyl-pentanol-(1)
  参考文献：
  名称：

  Rosenmund; Karg, Chemische Berichte, 1942, vol. 75, p. 1850,1856

  摘要：

  DOI：