4-[(2S,3R)-3-(4-Amino-butyl)-2-benzyloxycarbonyl-4-oxo-azetidine-1-carbonyl]-piperazine-1-carboxylic acid 1-isopropyl-2-methyl-propyl ester | 727724-86-9

• 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: 4-[(2S,3R)-3-(4-Amino-butyl)-2-benzyloxycarbonyl-4-oxo-azetidine-1-carbonyl]-piperazine-1-carboxylic acid 1-isopropyl-2-methyl-propyl ester
• 英文别名: 2,4-dimethylpentan-3-yl 4-[(3R,4S)-3-(4-aminobutyl)-2-oxo-4-phenylmethoxycarbonylazetidine-1-carbonyl]piperazine-1-carboxylate
• CAS: 727724-86-9
• 化学式: C₂₈H₄₂N₄O₆
• 分子量: 530.665
• InChiKey: LJNDAZIRRZVDDE-PKTZIBPZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  38
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  123
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  4-[(2S,3R)-3-(4-Amino-butyl)-2-benzyloxycarbonyl-4-oxo-azetidine-1-carbonyl]-piperazine-1-carboxylic acid 1-isopropyl-2-methyl-propyl ester 在 palladium on activated charcoal TEA 、 氢气 作用下， 以 1,4-二氧六环 为溶剂， 生成 4-[(2S,3R)-2-Carboxy-3-(4-guanidino-butyl)-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 nonguanidine azetidinone inhibitors of human tryptase

  摘要：

  Azetidinones such as BMS-363131 (2) and BMS-363130 (3), which contain a guanidine group in the C-3 side chain were previously shown to be very potent inhibitors of human tryptase with high selectivity versus other serine proteases, including trypsin. In this letter, we describe the discovery of a number of potent azetidinone tryptase inhibitors in which the guanidine moiety at the ring C-3 position is replaced with primary or secondary amine or aminopyridine functionality. In particular, BMS-354326 (4) is a highly potent tryptase inhibitor (IC50 1.8 nM), which has excellent selectivity against trypsin and most other related serine proteases. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.02.011
• 作为产物：
  描述：

  在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 生成 4-[(2S,3R)-3-(4-Amino-butyl)-2-benzyloxycarbonyl-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 nonguanidine azetidinone inhibitors of human tryptase

  摘要：

  Azetidinones such as BMS-363131 (2) and BMS-363130 (3), which contain a guanidine group in the C-3 side chain were previously shown to be very potent inhibitors of human tryptase with high selectivity versus other serine proteases, including trypsin. In this letter, we describe the discovery of a number of potent azetidinone tryptase inhibitors in which the guanidine moiety at the ring C-3 position is replaced with primary or secondary amine or aminopyridine functionality. In particular, BMS-354326 (4) is a highly potent tryptase inhibitor (IC50 1.8 nM), which has excellent selectivity against trypsin and most other related serine proteases. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.02.011