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 | 869494-43-9

• 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: 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
• CAS: 869494-43-9
• 化学式: C₃₅H₅₈N₄O₇Si
• 分子量: 674.954
• InChiKey: DEPBTLBFLXSJNX-ZLOCZDFZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.62
• 重原子数：
  47
• 可旋转键数：
  19
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  149
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  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 在 氢氟酸 作用下， 以 四氢呋喃 为溶剂， 反应 1.5h， 以61%的产率得到(E)-(S)-4-{(2R,4S,5S)-4-Hydroxy-6-methyl-2-(3-methyl-but-2-enyl)-5-[(5-methyl-isoxazole-3-carbonyl)-amino]-heptanoylamino}-5-((S)-2-oxo-pyrrolidin-3-yl)-pent-2-enoic acid ethyl ester
  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：

  L-谷氨酸 在 platinum(IV) oxide 锂硼氢 、 三甲基氯硅烷 、 氢气 、 三氧化硫吡啶 、 sodium carbonate 、 1-羟基苯并三唑 、 二甲基亚砜 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 、 三氟乙酸 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 二氯甲烷 、 氯仿 为溶剂， -78.0~23.0 ℃ 、344.74 kPa 条件下， 反应 53.34h， 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

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.