(2S,5S,8S,11S)-8-((R)-1-(benzyloxy)ethyl)-5-isobutyl-11-isopropyl-4,7,10,13-tetraoxo-2-((S)-2-oxopyrrolidin-3-yl)methyl-3,6,9,12-tetraazatetradecan-1-oic acid | 936371-47-0

• 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: (2S,5S,8S,11S)-8-((R)-1-(benzyloxy)ethyl)-5-isobutyl-11-isopropyl-4,7,10,13-tetraoxo-2-((S)-2-oxopyrrolidin-3-yl)methyl-3,6,9,12-tetraazatetradecan-1-oic acid
• 英文别名: Ac-Val-Thr(Bn)(Bn)-Leu-Ala((S)-2-oxopyrrolidin-3-yl)-OH；(2S)-2-[[(2S)-2-[[(2S,3R)-2-[[(2S)-2-acetamido-3-methylbutanoyl]amino]-3-phenylmethoxybutanoyl]amino]-4-methylpentanoyl]amino]-3-[(3S)-2-oxopyrrolidin-3-yl]propanoic acid
• CAS: 936371-47-0
• 化学式: C₃₁H₄₇N₅O₈
• 分子量: 617.743
• InChiKey: OJMGMXJWTDAIGH-ROMXMSMSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  44
• 可旋转键数：
  17
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  192
• 氢给体数：
  6
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (2S,5S,8S,11S)-8-((R)-1-(benzyloxy)ethyl)-5-isobutyl-11-isopropyl-4,7,10,13-tetraoxo-2-((S)-2-oxopyrrolidin-3-yl)methyl-3,6,9,12-tetraazatetradecan-1-oic acid 、 5-氯-3-羟基吡啶 在 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 以18%的产率得到(5S,8S,11S)-5-chloropyridin-3-yl 8-((R)-1-(benzyloxy)ethyl)-5-isobutyl-11-isopropyl-4,7,10,13-tetraoxo-2-((S)-2-oxopyrrolidin-3-yl)methyl-3,6,9,12-tetraazatetradecan-1-oate
  参考文献：
  名称：

  Design, Synthesis, and Evaluation of Inhibitors for Severe Acute Respiratory Syndrome 3C-Like Protease Based on Phthalhydrazide Ketones or Heteroaromatic Esters

  摘要：

  The 3C-like protease (3CL(pro)), which controls the severe acute respiratory syndrome (SARS) coronavirus replication, has been identified as a potential target for drug design in the treatment of SARS. A series of tetrapeptide phthalhydrazide ketones, pyridinyl esters, and their analogs have been designed, synthesized, and evaluated as potential SARS 3CL(pro) inhibitors. Some pyridinyl esters are identified as very potent inhibitors, with IC50 values in the nanomolar range (50-65 nM). Electrospray mass spectrometry indicates a mechanism involving acylation of the active site cysteine thiol for this class of inhibitors.

  DOI：

  10.1021/jm061425k
• 作为产物：
  描述：

  (alphaS,3S)-alpha-[(叔-丁基氧羰基)氨基]-2-氧代-3-吡咯烷丙酸甲酯 在 lithium hydroxide 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 2.0h， 生成 (2S,5S,8S,11S)-8-((R)-1-(benzyloxy)ethyl)-5-isobutyl-11-isopropyl-4,7,10,13-tetraoxo-2-((S)-2-oxopyrrolidin-3-yl)methyl-3,6,9,12-tetraazatetradecan-1-oic acid
  参考文献：
  名称：

  Design, Synthesis, and Evaluation of Inhibitors for Severe Acute Respiratory Syndrome 3C-Like Protease Based on Phthalhydrazide Ketones or Heteroaromatic Esters

  摘要：

  The 3C-like protease (3CL(pro)), which controls the severe acute respiratory syndrome (SARS) coronavirus replication, has been identified as a potential target for drug design in the treatment of SARS. A series of tetrapeptide phthalhydrazide ketones, pyridinyl esters, and their analogs have been designed, synthesized, and evaluated as potential SARS 3CL(pro) inhibitors. Some pyridinyl esters are identified as very potent inhibitors, with IC50 values in the nanomolar range (50-65 nM). Electrospray mass spectrometry indicates a mechanism involving acylation of the active site cysteine thiol for this class of inhibitors.

  DOI：

  10.1021/jm061425k