(2R,4S,5S)-5-tert-Butoxycarbonylamino-4-(tert-butyl-dimethyl-silanyloxy)-6-methyl-2-(3-methyl-but-2-enyl)-heptanoic acid | 869494-34-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (2R,4S,5S)-5-tert-Butoxycarbonylamino-4-(tert-butyl-dimethyl-silanyloxy)-6-methyl-2-(3-methyl-but-2-enyl)-heptanoic acid
• 英文别名: (2R,4S,5S)-4-[tert-butyl(dimethyl)silyl]oxy-6-methyl-2-(3-methylbut-2-enyl)-5-[(2-methylpropan-2-yl)oxycarbonylamino]heptanoic acid
• CAS: 869494-34-8
• 化学式: C₂₄H₄₇NO₅Si
• 分子量: 457.726
• InChiKey: AOZFBNWGXZFXME-AABGKKOBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.37
• 重原子数：
  31
• 可旋转键数：
  13
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  84.9
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2R,4S,5S)-5-tert-Butoxycarbonylamino-4-(tert-butyl-dimethyl-silanyloxy)-6-methyl-2-(3-methyl-but-2-enyl)-heptanoic acid 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 0.84h， 生成 ethyl (E,4S)-4-[[(2R,4S,5S)-4-[tert-butyl(dimethyl)silyl]oxy-6-methyl-2-(3-methylbut-2-enyl)-5-[(5-methyl-1,2-oxazole-3-carbonyl)amino]heptanoyl]amino]-5-[(3S)-2-oxopyrrolidin-3-yl]pent-2-enoate
  参考文献：
  名称：

  Design and Synthesis of Peptidomimetic Severe Acute Respiratory Syndrome Chymotrypsin-like Protease Inhibitors

  摘要：

  Design, synthesis, and biological evaluation of peptidomimetic severe acute respiratory syndrome chymotrypsin-like protease (SARS-3CLpro) inhibitors for severe acute respiratory syndrome coronavirus (SARS-CoV) are described. These inhibitors exhibited antiviral activity against SARS-CoV in infected cells in the micromolar range. An X-ray crystal structure of our lead inhibitor (4) bound to SARS-3CLpro provided important drug-design templates for the design of small-molecule inhibitors.

  DOI：

  10.1021/jm050548m
• 作为产物：
  描述：

  tert-butyl ((S)-2-methyl-1-((R)-5-oxotetrahydrofuran-2-yl)propyl)carbamate 在 咪唑 、 lithium hydroxide 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 50.67h， 生成 (2R,4S,5S)-5-tert-Butoxycarbonylamino-4-(tert-butyl-dimethyl-silanyloxy)-6-methyl-2-(3-methyl-but-2-enyl)-heptanoic acid
  参考文献：
  名称：

  Design and Synthesis of Peptidomimetic Severe Acute Respiratory Syndrome Chymotrypsin-like Protease Inhibitors

  摘要：

  Design, synthesis, and biological evaluation of peptidomimetic severe acute respiratory syndrome chymotrypsin-like protease (SARS-3CLpro) inhibitors for severe acute respiratory syndrome coronavirus (SARS-CoV) are described. These inhibitors exhibited antiviral activity against SARS-CoV in infected cells in the micromolar range. An X-ray crystal structure of our lead inhibitor (4) bound to SARS-3CLpro provided important drug-design templates for the design of small-molecule inhibitors.

  DOI：

  10.1021/jm050548m

文献信息

• Design and Synthesis of Peptidomimetic Severe Acute Respiratory Syndrome Chymotrypsin-like Protease Inhibitors
  作者：Arun K. Ghosh、Kai Xi、Kiira Ratia、Bernard D. Santarsiero、Wentao Fu、Brian H. Harcourt、Paul A. Rota、Susan C. Baker、Michael E. Johnson、Andrew D. Mesecar

  DOI：10.1021/jm050548m

  日期：2005.11.1

  Design, synthesis, and biological evaluation of peptidomimetic severe acute respiratory syndrome chymotrypsin-like protease (SARS-3CLpro) inhibitors for severe acute respiratory syndrome coronavirus (SARS-CoV) are described. These inhibitors exhibited antiviral activity against SARS-CoV in infected cells in the micromolar range. An X-ray crystal structure of our lead inhibitor (4) bound to SARS-3CLpro provided important drug-design templates for the design of small-molecule inhibitors.