(1R,2S)-2-(1-methylhydrazino)-1,2-diphenylethanol | 1279115-26-2

• 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: (1R,2S)-2-(1-methylhydrazino)-1,2-diphenylethanol
• 英文别名: (1R,2S)-2-[amino(methyl)amino]-1,2-diphenylethanol
• CAS: 1279115-26-2
• 化学式: C₁₅H₁₈N₂O
• 分子量: 242.321
• InChiKey: UZSBWSNIXUXPDF-LSDHHAIUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  49.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  D-酒石酸 、 (1R,2S)-2-(1-methylhydrazino)-1,2-diphenylethanol 以 乙醚 、 乙醇 为溶剂， 以1.1 g的产率得到(1R,2S)-2-(1-methylhydrazino)-1,2-diphenylethanol hemi-(S,S)-tartrate
  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
• 作为产物：
  描述：

  N-[(1S,2R)-2-hydroxy-1,2-diphenylethyl]-N-methylnitrous amide 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 生成 (1R,2S)-2-(1-methylhydrazino)-1,2-diphenylethanol
  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

• Inhibitors of copper-containing amine oxidases
  申请人：Biotie Therapies Corp.

  公开号：US20020173521A1

  公开（公告）日：2002-11-21

  The present invention is directed to hydrazono compounds that function as inhibitors of copper-containg amine oxidases commonly known as semicarbazide-sensitive amine oxidases (SSAO), including the human SSAO known as Vascular Adhesion Protein-1 (VAP-1). These SSAO inhibitors have therapeutic utility as drugs to treat conditions and diseases including, but not limited to, a number of inflammatory conditions and diseases (in particular chronic inflammatory conditions such as chronic arthritis, inflammatory bowel diseases, and chronic skin dermatoses), diseases related to carbohydrate metabolism and to aberrations in adipocyte differentiation or function and smooth muscle cell function, and vascular diseases. The compounds have the general formula: 1 or a pharmaceutically acceptable solvate, hydrate, or salt thereof, wherein R 1 to R 8 and X are as defined herein.

  本发明涉及一种作为铜含量胺氧化酶抑制剂的肼酰基化合物，这些胺氧化酶通常被称为半卡巴嗪敏感胺氧化酶（SSAO），包括人类已知的血管粘附蛋白-1（VAP-1）胺氧化酶。这些SSAO抑制剂在治疗条件和疾病方面具有治疗效用，包括但不限于许多炎症性疾病（特别是慢性炎症性疾病，如慢性关节炎、炎症性肠病和慢性皮肤皮肤病）、与碳水化合物代谢和脂肪细胞分化或功能异常以及平滑肌细胞功能以及血管疾病相关的疾病。这些化合物具有一般公式：1或其药学上可接受的溶剂、水合物或盐，其中R1至R8和X如本文所定义。
• USE OF VAP-1 INHIBITORS FOR TREATING FIBROTIC CONDITIONS
  申请人：Weston Christopher

  公开号：US20130195883A1

  公开（公告）日：2013-08-01

  The present invention relates to inhibitors of VAP-1 and their use as medicaments in treating fibrotic conditions. Furthermore, the present invention relates to a method of diagnosing a fibrotic condition on the basis of elevated level of soluble VAP-1 or SSAO activity in a bodily fluid, and to a kit for use in said diagnostic method.
• US6624202B2
  申请人：——

  公开号：US6624202B2

  公开（公告）日：2003-09-23
• US9795671B2
  申请人：——

  公开号：US9795671B2

  公开（公告）日：2017-10-24