(E)-(S)-4-[(2H-Chromene-3-carbonyl)-amino]-5-((S)-2-oxo-pyrrolidin-3-yl)-pent-2-enoic acid ethyl ester

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: (E)-(S)-4-[(2H-Chromene-3-carbonyl)-amino]-5-((S)-2-oxo-pyrrolidin-3-yl)-pent-2-enoic acid ethyl ester
• 英文别名: ethyl (E,4S)-4-(2H-chromene-3-carbonylamino)-5-[(3S)-2-oxopyrrolidin-3-yl]pent-2-enoate
• 化学式: C₂₁H₂₄N₂O₅
• 分子量: 384.432
• InChiKey: SJQVINWPPHUDDQ-CRLUXQHQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  28
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  93.7
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  N-[(1S)-1-(羟基甲基)-2-[(3S)-2-氧代-3-吡咯烷基]乙基]-氨基甲酸叔-丁酯 在 盐酸 、 N,N-二异丙基乙胺 、 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 、 2-碘酰基苯甲酸 作用下， 以 乙醇 、 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.5h， 生成 (E)-(S)-4-[(2H-Chromene-3-carbonyl)-amino]-5-((S)-2-oxo-pyrrolidin-3-yl)-pent-2-enoic acid ethyl ester
  参考文献：
  名称：

  Structure-Based Design of a Parallel Synthetic Array Directed Toward the Discovery of Irreversible Inhibitors of Human Rhinovirus 3C Protease

  摘要：

  Utilizing the tools of parallel synthesis and structure-based design, a new class of Michael acceptor-containing, irreversible inhibitors of human rhinovirus 3C protease (HRV 3CP) was discovered. These inhibitors are shown to inhibit HRV-14 3CP with rates of inactivation ranging from 886 to 31400 M-1 sec(-1). These inhibitors exhibit antiviral activity when tested against HRV-14 infected H1-HeLa cells, with EC50 values ranging from 1.94 to 0.15 muM. No cytotoxicity was observed at the limits of the assay concentration. A crystal structure of one of the more potent inhibitors covalently bound to HRV-2 3CP is detailed, These compounds were also tested against HRV serotypes other than type 14 and were found to have highly variable activities.

  DOI：

  10.1021/jm010435c