(2R,4S,5S)-5-azido-6-(3,5-difluorophenoxy)-4-hydroxy-2-methoxy-hexanoic acid cyclopropylamide | 1067651-90-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (2R,4S,5S)-5-azido-6-(3,5-difluorophenoxy)-4-hydroxy-2-methoxy-hexanoic acid cyclopropylamide
• 英文别名: (2R,4S,5S)-5-azido-N-cyclopropyl-6-(3,5-difluorophenoxy)-4-hydroxy-2-methoxyhexanamide
• CAS: 1067651-90-4
• 化学式: C₁₆H₂₀F₂N₄O₄
• 分子量: 370.356
• InChiKey: AGTZETWDQZJCDE-SOUVJXGZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  26
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  82.2
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (2R,4S,5S)-5-azido-6-(3,5-difluorophenoxy)-4-hydroxy-2-methoxy-hexanoic acid cyclopropylamide 在 水 、 三苯基膦 作用下， 以 甲醇 为溶剂， 生成
  参考文献：
  名称：

  Design and Synthesis of Potent and Selective BACE-1 Inhibitors

  摘要：

  Highly potent BACE-1 protease inhibitors have been developed from ill inhibitors containing a hydroxyethylene (HE) core displaying aryloxymethyl or benzyloxymethyl P1 side chain and a methoxy P1' side chain. The target molecules were synthesized in good overall yields from chiral carbohydrate starting materials. The inhibitors show high BACF-1 potency and good selectivity against cathepsin D, where the most potent inhibitor Furnishes BACE-1 Ki << 1 nM and displays > 1000-fold selectivity over cathepsin D.

  DOI：

  10.1021/jm901168f
• 作为产物：
  描述：

  5-azido-3,5-dideoxy-6-O-(3,5-difluorophenyl)-2-O-methyl-L-lyxo-1,4-lactone 、 环丙胺 在 2-羟基吡啶 、 N,N-二异丙基乙胺 作用下， 以82%的产率得到(2R,4S,5S)-5-azido-6-(3,5-difluorophenoxy)-4-hydroxy-2-methoxy-hexanoic acid cyclopropylamide
  参考文献：
  名称：

  Design and Synthesis of Potent and Selective BACE-1 Inhibitors

  摘要：

  Highly potent BACE-1 protease inhibitors have been developed from ill inhibitors containing a hydroxyethylene (HE) core displaying aryloxymethyl or benzyloxymethyl P1 side chain and a methoxy P1' side chain. The target molecules were synthesized in good overall yields from chiral carbohydrate starting materials. The inhibitors show high BACF-1 potency and good selectivity against cathepsin D, where the most potent inhibitor Furnishes BACE-1 Ki << 1 nM and displays > 1000-fold selectivity over cathepsin D.

  DOI：

  10.1021/jm901168f

文献信息

• Design and Synthesis of Potent and Selective BACE-1 Inhibitors
  作者：Catarina Björklund、Stefan Oscarson、Kurt Benkestock、Neera Borkakoti、Katarina Jansson、Jimmy Lindberg、Lotta Vrang、Anders Hallberg、Åsa Rosenquist、Bertil Samuelsson

  DOI：10.1021/jm901168f

  日期：2010.2.25

  Highly potent BACE-1 protease inhibitors have been developed from ill inhibitors containing a hydroxyethylene (HE) core displaying aryloxymethyl or benzyloxymethyl P1 side chain and a methoxy P1' side chain. The target molecules were synthesized in good overall yields from chiral carbohydrate starting materials. The inhibitors show high BACF-1 potency and good selectivity against cathepsin D, where the most potent inhibitor Furnishes BACE-1 Ki << 1 nM and displays > 1000-fold selectivity over cathepsin D.