(2S,3R)-3-Azetidin-3-ylmethyl-4-oxo-azetidine-2-carboxylic acid benzyl ester | 253176-98-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酰胺类
• 英文名称: (2S,3R)-3-Azetidin-3-ylmethyl-4-oxo-azetidine-2-carboxylic acid benzyl ester
• CAS: 253176-98-6
• 化学式: C₁₅H₁₈N₂O₃
• 分子量: 274.32
• InChiKey: HOFIMEJYJFKEKA-OLZOCXBDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.45
• 重原子数：
  20.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  67.43
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (2S,3R)-3-Azetidin-3-ylmethyl-4-oxo-azetidine-2-carboxylic acid benzyl ester 在 4-二甲氨基吡啶 、 TEA 、 mercury(II) diacetate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 4-[(2S,3R)-2-Benzyloxycarbonyl-3-(1-{benzyloxycarbonylamino-[(E)-benzyloxycarbonylimino]-methyl}-azetidin-3-ylmethyl)-4-oxo-azetidine-1-carbonyl]-piperazine-1-carboxylic acid 1-isopropyl-2-methyl-propyl ester
  参考文献：
  名称：

  Synthesis of potent and highly selective inhibitors of human tryptase

  摘要：

  The serine protease tryptase has been implicated in allergic and inflammatory diseases and associated with asthma. The synthesis and SAR of a series of N1-activated-4-carboxy azetidinones are described, resulting in identification of BMS-363131 (2) as a potent inhibitor of human tryptase (IC50 < 1.7 nM) with high selectivity (>3000-fold) for tryptase versus related serine proteases including trypsin. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00689-3
• 作为产物：
  描述：

  (2S,3R)-3-(1-tert-Butoxycarbonyl-azetidin-3-ylmethyl)-4-oxo-azetidine-2-carboxylic acid 在 碳酸氢钠 、 三氟乙酸 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 (2S,3R)-3-Azetidin-3-ylmethyl-4-oxo-azetidine-2-carboxylic acid benzyl ester
  参考文献：
  名称：

  Synthesis of potent and highly selective inhibitors of human tryptase

  摘要：

  The serine protease tryptase has been implicated in allergic and inflammatory diseases and associated with asthma. The synthesis and SAR of a series of N1-activated-4-carboxy azetidinones are described, resulting in identification of BMS-363131 (2) as a potent inhibitor of human tryptase (IC50 < 1.7 nM) with high selectivity (>3000-fold) for tryptase versus related serine proteases including trypsin. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00689-3