{4-[((S)-1-{(S)-2-[(S)-1-(4-Hydroxy-benzooxazole-2-carbonyl)-2-methyl-propylcarbamoyl]-pyrrolidine-1-carbonyl}-2-methyl-propylcarbamoyl)-methoxy]-phenoxy}-acetic acid tert-butyl ester | 437756-34-8

• 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-[((S)-1-{(S)-2-[(S)-1-(4-Hydroxy-benzooxazole-2-carbonyl)-2-methyl-propylcarbamoyl]-pyrrolidine-1-carbonyl}-2-methyl-propylcarbamoyl)-methoxy]-phenoxy}-acetic acid tert-butyl ester
• CAS: 437756-34-8
• 化学式: C₃₆H₄₆N₄O₁₀
• 分子量: 694.782
• InChiKey: ZKQRRFSMQPUSDW-YDZBWFOPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.79
• 重原子数：
  50.0
• 可旋转键数：
  14.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  186.6
• 氢给体数：
  3.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  {4-[((S)-1-{(S)-2-[(S)-1-(4-Hydroxy-benzooxazole-2-carbonyl)-2-methyl-propylcarbamoyl]-pyrrolidine-1-carbonyl}-2-methyl-propylcarbamoyl)-methoxy]-phenoxy}-acetic acid tert-butyl ester 在 三乙胺 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 生成 2,2-Dimethyl-propionic acid 2-{(S)-2-[((S)-1-{(S)-2-[2-(4-carboxymethoxy-phenoxy)-acetylamino]-3-methyl-butyryl}-pyrrolidine-2-carbonyl)-amino]-3-methyl-butyryl}-benzooxazol-4-yl ester
  参考文献：
  名称：

  Design and Synthesis of Peptide-Based Carboxylic Acid-Containing Transition-State Inhibitors of Human Neutrophil Elastase

  摘要：

  In our search for a new agent, human neutrophil elastase (HNE) inhibitor, for the treatment of acute respiratory failure, we rationally designed and synthesized a series of peptide-based carboxylic acid-containing transition-state inhibitors. The presence of valyl moiety is found to be essential for potent in vitro inhibitory activity and also prevention of an undesirable toxicity. Of these, compound 9m has the most potent in vivo effect on TINE-induced lung hemorrhage in hamsters. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(01)00797-1
• 作为产物：
  描述：

  (S)-1-((S)-2-Amino-3-methyl-butyryl)-pyrrolidine-2-carboxylic acid ((S)-1-{[4-(tert-butyl-dimethyl-silanyloxy)-benzooxazol-2-yl]-hydroxy-methyl}-2-methyl-propyl)-amide 在 吡啶 、 四丁基氟化铵 、 戴斯-马丁氧化剂 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 {4-[((S)-1-{(S)-2-[(S)-1-(4-Hydroxy-benzooxazole-2-carbonyl)-2-methyl-propylcarbamoyl]-pyrrolidine-1-carbonyl}-2-methyl-propylcarbamoyl)-methoxy]-phenoxy}-acetic acid tert-butyl ester
  参考文献：
  名称：

  Design and Synthesis of Peptide-Based Carboxylic Acid-Containing Transition-State Inhibitors of Human Neutrophil Elastase

  摘要：

  In our search for a new agent, human neutrophil elastase (HNE) inhibitor, for the treatment of acute respiratory failure, we rationally designed and synthesized a series of peptide-based carboxylic acid-containing transition-state inhibitors. The presence of valyl moiety is found to be essential for potent in vitro inhibitory activity and also prevention of an undesirable toxicity. Of these, compound 9m has the most potent in vivo effect on TINE-induced lung hemorrhage in hamsters. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(01)00797-1