(1S,2S)-2-(1-methylhydrazino)-1,2-diphenylethanol fumarate | 1279115-31-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: (1S,2S)-2-(1-methylhydrazino)-1,2-diphenylethanol fumarate
• 英文别名: (1S,2S)-2-[amino(methyl)amino]-1,2-diphenylethanol;(E)-but-2-enedioic acid
• CAS: 1279115-31-9
• 化学式: C₄H₄O₄*C₁₅H₁₈N₂O
• 分子量: 358.394
• InChiKey: RCRMNKDMXUYVBC-JUYOPONZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.98
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  124
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  N-[(1S,2S)-2-hydroxy-1,2-diphenylethyl]-N-methylnitrous amide 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 、 乙醚 、 乙醇 为溶剂， 生成 (1S,2S)-2-(1-methylhydrazino)-1,2-diphenylethanol fumarate
  参考文献：
  名称：

  Novel Hydrazine Molecules as Tools To Understand the Flexibility of Vascular Adhesion Protein-1 Ligand-Binding Site: Toward More Selective Inhibitors

  摘要：

  Vascular adhesion protein-1 (VAP-1) belongs to a family of amine oxidases. It plays a role in leukocyte trafficking and in amine compound metabolism. VAP-1 is linked to various diseases, such as Alzheimer's disease, psoriasis, depression, diabetes, and obesity. Accordingly, selective inhibitors of VAP-1 could potentially be used to treat those diseases. In this study, eight novel VAP-1 hydrazine derivatives were synthesized and their VAP-1 and monoamine oxidase (MAO) inhibition ability was determined in vitro. MD simulations of VAP-1 with these new molecules reveal that the VAP-1 ligand-binding pocket is flexible and capable of fitting substantially larger ligands than was previously believed. The increase in the size of the VAP-1 ligands, together with the methylation of the secondary nitrogen atom of the hydrazine moiety, improves the VAP-1 selectivity over MAO.

  DOI：

  10.1021/jm200059p

文献信息

• Novel Hydrazine Molecules as Tools To Understand the Flexibility of Vascular Adhesion Protein-1 Ligand-Binding Site: Toward More Selective Inhibitors
  作者：Elisa M. Nurminen、Marjo Pihlavisto、László Lázár、Ulla Pentikäinen、Ferenc Fülöp、Olli T. Pentikäinen

  DOI：10.1021/jm200059p

  日期：2011.4.14

  Vascular adhesion protein-1 (VAP-1) belongs to a family of amine oxidases. It plays a role in leukocyte trafficking and in amine compound metabolism. VAP-1 is linked to various diseases, such as Alzheimer's disease, psoriasis, depression, diabetes, and obesity. Accordingly, selective inhibitors of VAP-1 could potentially be used to treat those diseases. In this study, eight novel VAP-1 hydrazine derivatives were synthesized and their VAP-1 and monoamine oxidase (MAO) inhibition ability was determined in vitro. MD simulations of VAP-1 with these new molecules reveal that the VAP-1 ligand-binding pocket is flexible and capable of fitting substantially larger ligands than was previously believed. The increase in the size of the VAP-1 ligands, together with the methylation of the secondary nitrogen atom of the hydrazine moiety, improves the VAP-1 selectivity over MAO.