(S)-tert-butyl (1-((2-chloro-4-nitrophenyl)amino)-1-oxo-3-phenylpropan-2-yl)carbamate | 860399-69-5

• 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)-tert-butyl (1-((2-chloro-4-nitrophenyl)amino)-1-oxo-3-phenylpropan-2-yl)carbamate
• 英文别名: tert-butyl N-[(1S)-1-benzyl-2-(2-chloro-4-nitro-anilino)-2-oxo-ethyl]carbamate；tert-butyl N-[(2S)-1-(2-chloro-4-nitroanilino)-1-oxo-3-phenylpropan-2-yl]carbamate
• CAS: 860399-69-5
• 化学式: C₂₀H₂₂ClN₃O₅
• 分子量: 419.865
• InChiKey: HYZBCWMHQHPKRE-KRWDZBQOSA-N

物化性质

• 沸点：
  626.8±55.0 °C(Predicted)
• 密度：
  1.317±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  29
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  113
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (S)-tert-butyl (1-((2-chloro-4-nitrophenyl)amino)-1-oxo-3-phenylpropan-2-yl)carbamate 在 N-甲基吗啉 、 盐酸 作用下， 以 1,4-二氧六环 、 二氯甲烷 为溶剂， 反应 1.5h， 生成 N-[(1S)-1-benzyl-2-(2-chloro-4-nitro-anilino)-2-oxo-ethyl]-2-bromo-hexadecanamide
  参考文献：
  名称：

  Discovery of Potent Anilide Inhibitors against the Severe Acute Respiratory Syndrome 3CL Protease

  摘要：

  A diversified library of peptide anilides was prepared, and their inhibition activities against the SARS-CoV 3CL protease were examined by a fluorogenic tetradecapeptide substrate. The most potent inhibitor is an anilide derived from 2-chloro-4-nitroaniline, L-phenylalanine and 4-(dimethylamino)benzoic acid. This anilide is a competitive inhibitor of the SARS-CoV 3CL protease with K-i = 0.03 mu M. The molecular docking experiment indicates that the P1 residue of this anilide inhibitor is distant from the nucleophilic SH of Cys145 in the active site.

  DOI：

  10.1021/jm050184y
• 作为产物：
  描述：

  BOC-L-苯丙氨酸 、 2-氯-4-硝基苯胺 在 三氯氧磷 作用下， 以 吡啶 为溶剂， 反应 1.5h， 以78%的产率得到(S)-tert-butyl (1-((2-chloro-4-nitrophenyl)amino)-1-oxo-3-phenylpropan-2-yl)carbamate
  参考文献：
  名称：

  Discovery of Potent Anilide Inhibitors against the Severe Acute Respiratory Syndrome 3CL Protease

  摘要：

  A diversified library of peptide anilides was prepared, and their inhibition activities against the SARS-CoV 3CL protease were examined by a fluorogenic tetradecapeptide substrate. The most potent inhibitor is an anilide derived from 2-chloro-4-nitroaniline, L-phenylalanine and 4-(dimethylamino)benzoic acid. This anilide is a competitive inhibitor of the SARS-CoV 3CL protease with K-i = 0.03 mu M. The molecular docking experiment indicates that the P1 residue of this anilide inhibitor is distant from the nucleophilic SH of Cys145 in the active site.

  DOI：

  10.1021/jm050184y

文献信息

• Discovery of Potent Anilide Inhibitors against the Severe Acute Respiratory Syndrome 3CL Protease
  作者：Jiun-Jie Shie、Jim-Min Fang、Chih-Jung Kuo、Tun-Hsun Kuo、Po-Huang Liang、Hung-Jyun Huang、Wen-Bin Yang、Chun-Hung Lin、Jiun-Ling Chen、Yin-Ta Wu、Chi-Huey Wong

  DOI：10.1021/jm050184y

  日期：2005.6.1

  A diversified library of peptide anilides was prepared, and their inhibition activities against the SARS-CoV 3CL protease were examined by a fluorogenic tetradecapeptide substrate. The most potent inhibitor is an anilide derived from 2-chloro-4-nitroaniline, L-phenylalanine and 4-(dimethylamino)benzoic acid. This anilide is a competitive inhibitor of the SARS-CoV 3CL protease with K-i = 0.03 mu M. The molecular docking experiment indicates that the P1 residue of this anilide inhibitor is distant from the nucleophilic SH of Cys145 in the active site.