Acetic acid (2S,3S)-3-[(1-benzyloxycarbonylamino-cyclohexanecarbonyl)-amino]-4-oxo-azetidin-2-yl ester | 455253-68-6

• 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: Acetic acid (2S,3S)-3-[(1-benzyloxycarbonylamino-cyclohexanecarbonyl)-amino]-4-oxo-azetidin-2-yl ester
• 英文别名: [(2S,3S)-4-oxo-3-[[1-(phenylmethoxycarbonylamino)cyclohexanecarbonyl]amino]azetidin-2-yl] acetate
• CAS: 455253-68-6
• 化学式: C₂₀H₂₅N₃O₆
• 分子量: 403.435
• InChiKey: DZHKQXPPMAFVCH-WBVHZDCISA-N

物化性质

• 沸点：
  702.6±60.0 °C(Predicted)
• 密度：
  1.31±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  29
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  123
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  Acetic acid (2S,3S)-3-[(1-benzyloxycarbonylamino-cyclohexanecarbonyl)-amino]-4-oxo-azetidin-2-yl ester 在 palladium on activated charcoal 氢气 、 N,N-二异丙基乙胺 、 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 作用下， 以 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 20.0 ℃ 、344.74 kPa 条件下， 反应 26.0h， 生成 [(2S,3S)-3-[[1-[[4-[2-(dimethylamino)-1,3-thiazol-4-yl]benzoyl]amino]cyclohexanecarbonyl]amino]-4-oxoazetidin-2-yl] acetate
  参考文献：
  名称：

  3,4-Disubstituted azetidinones as selective inhibitors of the cysteine protease cathepsin K. Exploring P3 elements for potency and selectivity

  摘要：

  The synthesis of a series of highly potent and selective inhibitors of cathepsin K based on the 3,4-disubstituted azetidin-2-one warhead is reported. A high degree of potency and selectivity was achieved by introducing a basic nitrogen into the distal part of the P3 element of the molecule. Data from kinetic and mass spectrometry experiments are consistent with the interpretation that compounds of this series transiently acylate the sulfhydrile of cathepsin K. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.12.088
• 作为产物：
  描述：

  (3S,4S)-3-benzyloxycarbonylamino-4-acetoxy-azetidin-2-one 在 palladium on activated charcoal 氢气 、 N,N-二异丙基乙胺 、 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 作用下， 以 四氢呋喃 、 乙酸乙酯 为溶剂， 20.0 ℃ 、344.74 kPa 条件下， 反应 26.0h， 生成 Acetic acid (2S,3S)-3-[(1-benzyloxycarbonylamino-cyclohexanecarbonyl)-amino]-4-oxo-azetidin-2-yl ester
  参考文献：
  名称：

  3,4-Disubstituted azetidinones as selective inhibitors of the cysteine protease cathepsin K. Exploring P2 elements for selectivity

  摘要：

  A novel series of 3,4-disubstituted azetiditiones based inhibitors of the cysteine protease cathepsin K (Cat K) has been identified. Although not optimized, some of these compounds show at least 100-fold selectivity against other cathepsins. The use of cyclic moieties as P2 elements has proven to be crucial to achieve a high degree of selectivity. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00304-4