(S)-1-amino-4-methylpentan-3-ol | 1446827-57-1

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (S)-1-amino-4-methylpentan-3-ol
• 英文别名: (3S)-1-amino-4-methylpentan-3-ol
• CAS: 1446827-57-1
• 化学式: C₆H₁₅NO
• 分子量: 117.191
• InChiKey: ZTKFDYZSGCIKNI-LURJTMIESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  8
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  46.2
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  (S)-3-hydroxy-4-methylpentanenitrile 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 反应 0.5h， 生成 (S)-1-amino-4-methylpentan-3-ol
  参考文献：
  名称：

  Carbamoyl Pyridone HIV-1 Integrase Inhibitors 3. A Diastereomeric Approach to Chiral Nonracemic Tricyclic Ring Systems and the Discovery of Dolutegravir (S/GSK1349572) and (S/GSK1265744)

  摘要：

  We report herein the discovery of the human immunodeficiency virus type-1 (HIV-1) integrase inhibitors dolutegravir (S/GSK1349572) (3) and S/GSK1265744 (4). These drugs stem from a series of carbamoyl pyridone analogues designed using a two-metal chelation model of the integrase catalytic active site. Structure-activity studies evolved a tricyclic series of carbamoyl pyridines that demonstrated properties indicative of once-daily dosing and superior potency against resistant viral strains. An inherent hemiaminal ring fusion stereocenter within the tricyclic carbamoyl pyridone scaffold led to a critical substrate controlled diastereo-selective synthetic strategy whereby chiral information from small readily available amino alcohols was employed to control relative and absolute stereochemistry of the final drug candidates. Modest to extremely high levels of stereochemical control were observed depending on ring size and position of the stereocenter. This approach resulted in the discovery of 3 and 4, which are currently in clinical development.

  DOI：

  10.1021/jm400645w

文献信息

• MODULATIONS OF PROTEASE ACTIVATED RECEPTORS
  申请人：Fairlie David Paul

  公开号：US20130184226A1

  公开（公告）日：2013-07-18

  The present invention provides novel compounds of the Formula (1), pharmaceutical compositions comprising such compounds and methods for using such compounds as tools for biological studies or as agents or drugs for modulating Protease Activated Receptor-2 (PAR2) and for treating a subject at risk of—or susceptible to—a disease or disorder, or having a disease or disorder associated with undesirable PAR2 activity.
• MODULATORS OF PROTEASE ACTIVATED RECEPTORS
  申请人：Fairlie David

  公开号：US20140315796A1

  公开（公告）日：2014-10-23

  The present invention provides novel compounds of the Formula (I), pharmaceutical compositions comprising such compounds and methods for using such compounds as tools for biological studies or as agents or drugs for therapies such as metabolic syndrome, obesity, type II diabetes, fibrosis and cardiovascular diseases, whether they are used alone or in combination with other treatment modalities.
• US8901085B2
  申请人：——

  公开号：US8901085B2

  公开（公告）日：2014-12-02
• US8927503B2
  申请人：——

  公开号：US8927503B2

  公开（公告）日：2015-01-06
• US9701711B2
  申请人：——

  公开号：US9701711B2

  公开（公告）日：2017-07-11