{(S)-1-[1-(2-Dimethylcarbamoyl-ethyl)-3-fluoro-2-hydroxy-propylcarbamoyl]-2-methyl-propyl}-carbamic acid benzyl ester | 877221-67-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 肽模拟物
• 英文名称: {(S)-1-[1-(2-Dimethylcarbamoyl-ethyl)-3-fluoro-2-hydroxy-propylcarbamoyl]-2-methyl-propyl}-carbamic acid benzyl ester
• CAS: 877221-67-5
• 化学式: C₂₁H₃₂FN₃O₅
• 分子量: 425.501
• InChiKey: SFYFBFNAHANBMK-TVPLGVNVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.62
• 重原子数：
  30.0
• 可旋转键数：
  11.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  107.97
• 氢给体数：
  3.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  {(S)-1-[1-(2-Dimethylcarbamoyl-ethyl)-3-fluoro-2-hydroxy-propylcarbamoyl]-2-methyl-propyl}-carbamic acid benzyl ester 在 戴斯-马丁氧化剂 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以97%的产率得到4-(Cbz-Val-amido)-6-fluoro-5-oxo-hexanoic acid dimethylamide
  参考文献：
  名称：

  Design and Synthesis of Dipeptidyl Glutaminyl Fluoromethyl Ketones as Potent Severe Acute Respiratory Syndrome Coronovirus (SARS-CoV) Inhibitors

  摘要：

  This paper describes the design and synthesis of dipeptidyl N,N-dimethyl glutaminyl fluoromethyl ketones (fmk) as severe acute respiratory syndrome coronovirus (SARS-CoV) inhibitors. The compounds were tested against SARS-CoV-induced cell death in Vero or CaCo2 cells as a measurement of the inhibiting effects of the compounds on the replication of the virus. Z-Leu-Gln(NMe2)-fmk (6a) was found to be a potent inhibitor with low toxicity in cells, protecting cells with an EC50 value of 2.5 mu M and exhibiting a selectivity index of > 40.

  DOI：

  10.1021/jm0507678
• 作为产物：
  描述：

  6-fluoro-5-hydroxy-4-nitrohexanoic acid dimethylamide 在 镍 4-二甲氨基吡啶 、 氢气 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 20.0 ℃ 、310.26 kPa 条件下， 反应 6.17h， 生成 {(S)-1-[1-(2-Dimethylcarbamoyl-ethyl)-3-fluoro-2-hydroxy-propylcarbamoyl]-2-methyl-propyl}-carbamic acid benzyl ester
  参考文献：
  名称：

  Design and Synthesis of Dipeptidyl Glutaminyl Fluoromethyl Ketones as Potent Severe Acute Respiratory Syndrome Coronovirus (SARS-CoV) Inhibitors

  摘要：

  This paper describes the design and synthesis of dipeptidyl N,N-dimethyl glutaminyl fluoromethyl ketones (fmk) as severe acute respiratory syndrome coronovirus (SARS-CoV) inhibitors. The compounds were tested against SARS-CoV-induced cell death in Vero or CaCo2 cells as a measurement of the inhibiting effects of the compounds on the replication of the virus. Z-Leu-Gln(NMe2)-fmk (6a) was found to be a potent inhibitor with low toxicity in cells, protecting cells with an EC50 value of 2.5 mu M and exhibiting a selectivity index of > 40.

  DOI：

  10.1021/jm0507678