tert-butyl (S)-1-((2S,4R)-tetrahydro-4-(3-methylbut-2-enyl)-5-oxofuran-2-yl)-2-methylpropylcarbamate | 869494-38-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: tert-butyl (S)-1-((2S,4R)-tetrahydro-4-(3-methylbut-2-enyl)-5-oxofuran-2-yl)-2-methylpropylcarbamate
• 英文别名: tert-butyl N-[(1S)-2-methyl-1-[(2S,4R)-4-(3-methylbut-2-enyl)-5-oxooxolan-2-yl]propyl]carbamate
• CAS: 869494-38-2
• 化学式: C₁₈H₃₁NO₄
• 分子量: 325.448
• InChiKey: FGCWLRONWHKXBC-ILXRZTDVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  tert-butyl (S)-1-((2S,4R)-tetrahydro-4-(3-methylbut-2-enyl)-5-oxofuran-2-yl)-2-methylpropylcarbamate 在 咪唑 、 lithium hydroxide 、 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 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 48.84h， 生成 ethyl (E,4S)-4-[[(2R,4S,5S)-4-[tert-butyl(dimethyl)silyl]oxy-6-methyl-2-(3-methylbut-2-enyl)-5-[(2-methylpropan-2-yl)oxycarbonylamino]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：

  (4S,5S)-5-tert-Butoxycarbonylamino-4-hydroxy-6-methyl-heptanoic acid ethyl ester 在 溶剂黄146 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 、 甲苯 为溶剂， 反应 14.0h， 生成 tert-butyl (S)-1-((2S,4R)-tetrahydro-4-(3-methylbut-2-enyl)-5-oxofuran-2-yl)-2-methylpropylcarbamate
  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.