(S)-3-Amino-4-(4-hydroxy-phenylamino)-butyric acid benzyl ester | 331843-16-4

• 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: (S)-3-Amino-4-(4-hydroxy-phenylamino)-butyric acid benzyl ester
• CAS: 331843-16-4
• 化学式: C₁₇H₂₀N₂O₃
• 分子量: 300.357
• InChiKey: PXVWXORVTIHMCQ-AWEZNQCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.26
• 重原子数：
  22.0
• 可旋转键数：
  7.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  84.58
• 氢给体数：
  3.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (S)-3-Amino-4-(4-hydroxy-phenylamino)-butyric acid benzyl ester 、 N-acetyl-L-aspartyl-L-valinyl-L-alanine β-benzyl ester 在 palladium on activated charcoal 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 三乙胺 、 氢气 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以65%的产率得到3-(S)-N-(N'-acetyl-L-aspartyl-L-valinyl-L-alanyl)-4-N''-(p-hydroxylphenyl)-butyric acid
  参考文献：
  名称：

  N-Nitrosoanilines: a new class of caspase-3 inhibitors

  摘要：

  Caspases are a family of cysteine proteases activated during apoptosis. In cultured human endothelial cells, physiological levels of NO prevent apoptosis and interfere with the activation of the caspase cascade. Previous studies have demonstrated that NO inhibits the activity of caspase-3 by S-nitrosylation of the enzyme. In this study, the inhibitory effect of a new class of NO donors, N-nitrosoaniline derivatives, were examined against caspase-3. Initially eight small molecule inhibitors bearing N-nitroso moieties were assayed. It was found that the presence of an electron-donating group on the phenyl ring led to better inhibitory potency, a trend consistent with the results from the previous papain studies. Based on the analysis of the enzyme and substrates' structures, two peptidyl N-nitrosoaniline inhibitors [Ac-DVAD-NNO (1) and Ac-DV-AMO (2)] were designed and synthesized. Both compounds exhibited enhanced inhibitory potency against caspase-3. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(00)00222-4
• 作为产物：
  描述：

  Boc-L-天冬氨酸 4-苄酯 在 N-甲基吗啉 、 草酰氯 、 sodium cyanoborohydride 、 二甲基亚砜 、 三乙胺 、 氯甲酸异丁酯 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 2.67h， 生成 (S)-3-Amino-4-(4-hydroxy-phenylamino)-butyric acid benzyl ester
  参考文献：
  名称：

  N-Nitrosoanilines: a new class of caspase-3 inhibitors

  摘要：

  Caspases are a family of cysteine proteases activated during apoptosis. In cultured human endothelial cells, physiological levels of NO prevent apoptosis and interfere with the activation of the caspase cascade. Previous studies have demonstrated that NO inhibits the activity of caspase-3 by S-nitrosylation of the enzyme. In this study, the inhibitory effect of a new class of NO donors, N-nitrosoaniline derivatives, were examined against caspase-3. Initially eight small molecule inhibitors bearing N-nitroso moieties were assayed. It was found that the presence of an electron-donating group on the phenyl ring led to better inhibitory potency, a trend consistent with the results from the previous papain studies. Based on the analysis of the enzyme and substrates' structures, two peptidyl N-nitrosoaniline inhibitors [Ac-DVAD-NNO (1) and Ac-DV-AMO (2)] were designed and synthesized. Both compounds exhibited enhanced inhibitory potency against caspase-3. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(00)00222-4