(2S,3S)-2-amino-3-hydroxy-N-isopropylhexanamide | 1399317-96-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (2S,3S)-2-amino-3-hydroxy-N-isopropylhexanamide
• 英文别名: (2S,3S)-2-amino-3-hydroxy-N-propan-2-ylhexanamide
• CAS: 1399317-96-4
• 化学式: C₉H₂₀N₂O₂
• 分子量: 188.27
• InChiKey: VFCUOULBUZLQTP-YUMQZZPRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  13
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  75.4
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2S,3S)-2-amino-3-hydroxy-N-isopropylhexanamide 在 三乙酰氧基硼氢化钠 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 17.5h， 生成
  参考文献：
  名称：

  Structure-Based Design of Highly Selective β-Secretase Inhibitors: Synthesis, Biological Evaluation, and Protein–Ligand X-ray Crystal Structure

  摘要：

  The structure-based design, synthesis, and X-ray structure of protein-ligand complexes of exceptionally potent and selective beta-secretase inhibitors are described. The inhibitors are designed specifically to interact with S-1' active site residues to provide selectivity over memapsin 1 and cathepsin D. Inhibitor 5 has exhibited exceedingly potent inhibitory activity (K-i = 17 pM) and high selectivity over BACE 2 (>7000-fold) and cathepsin D (>250000-fold). A protein ligand crystal structure revealed important molecular insight into these selectivities. These interactions may serve as an important guide to design selectivity over the physiologically important aspartic acid proteases.

  DOI：

  10.1021/jm3008823
• 作为产物：
  描述：

  (2R,3S)-ethyl 2,3-dihydroxyhexanoate 在 sodium azide 、 lithium hydroxide monohydrate 、 10% Pd/C 、 氢气 、 1-羟基苯并三唑一水物 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 、 N,N-二异丙基乙胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 81.5h， 生成 (2S,3S)-2-amino-3-hydroxy-N-isopropylhexanamide
  参考文献：
  名称：

  Structure-Based Design of Highly Selective β-Secretase Inhibitors: Synthesis, Biological Evaluation, and Protein–Ligand X-ray Crystal Structure

  摘要：

  The structure-based design, synthesis, and X-ray structure of protein-ligand complexes of exceptionally potent and selective beta-secretase inhibitors are described. The inhibitors are designed specifically to interact with S-1' active site residues to provide selectivity over memapsin 1 and cathepsin D. Inhibitor 5 has exhibited exceedingly potent inhibitory activity (K-i = 17 pM) and high selectivity over BACE 2 (>7000-fold) and cathepsin D (>250000-fold). A protein ligand crystal structure revealed important molecular insight into these selectivities. These interactions may serve as an important guide to design selectivity over the physiologically important aspartic acid proteases.

  DOI：

  10.1021/jm3008823

文献信息

• Inhibitors of Memapsin 2 Cleavage for the Treatment of Alzheimer's Disease
  申请人：Purdue Research Foundation

  公开号：US20140066488A1

  公开（公告）日：2014-03-06

  Proteases such as memapsin 2 are important enzymes, playing roles in a variety of diseases including Alzheimer's Disease. The inventors have developed inhibitors of memapsin 2 and methods of use therefore in the treatment of disease.

  蛋白酶如膜蛋白酶2是重要的酶，发挥着在各种疾病中的作用，包括阿尔茨海默病。发明者已经开发了膜蛋白酶2的抑制剂以及在治疗疾病中使用的方法。
• [EN] INHIBITORS OF MEMAPSIN 2 CLEAVAGE FOR THE TREATMENT OF ALZHEIMER'S DISEASE<br/>[FR] INHIBITEURS DE CLIVAGE DE LA MÉMAPSINE 2 POUR LE TRAITEMENT DE LA MALADIE D'ALZHEIMER
  申请人：OKLAHOMA MED RES FOUND

  公开号：WO2014036105A2

  公开（公告）日：2014-03-06

  Proteases such as memapsin 2 are important enzymes, playing roles in a variety of diseases including Alzheimer's Disease. The inventors have developed inhibitors of memapsin 2 and methods of use therefore in the treatment of disease.