(E)-(S)-4-((S)-2-{(S)-2-[((S)-2,5-Dihydro-1H-pyrrole-2-carbonyl)-amino]-4-methyl-pentanoylamino}-3-phenyl-propionylamino)-6-(trityl-carbamoyl)-hex-2-enoic acid ethyl ester | 226922-64-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 肽模拟物
• 英文名称: (E)-(S)-4-((S)-2-{(S)-2-[((S)-2,5-Dihydro-1H-pyrrole-2-carbonyl)-amino]-4-methyl-pentanoylamino}-3-phenyl-propionylamino)-6-(trityl-carbamoyl)-hex-2-enoic acid ethyl ester
• CAS: 226922-64-1
• 化学式: C₄₈H₅₅N₅O₆
• 分子量: 797.995
• InChiKey: PFWKDUIZYAIWLG-YZURPHIMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.27
• 重原子数：
  59.0
• 可旋转键数：
  20.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  154.73
• 氢给体数：
  5.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  (E)-(S)-4-((S)-2-{(S)-2-[((S)-2,5-Dihydro-1H-pyrrole-2-carbonyl)-amino]-4-methyl-pentanoylamino}-3-phenyl-propionylamino)-6-(trityl-carbamoyl)-hex-2-enoic acid ethyl ester 在 三异丙基硅烷 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 生成 (E)-(S)-6-Carbamoyl-4-((S)-2-{(S)-2-[((S)-2,5-dihydro-1H-pyrrole-2-carbonyl)-amino]-4-methyl-pentanoylamino}-3-phenyl-propionylamino)-hex-2-enoic acid ethyl ester
  参考文献：
  名称：

  Solid-phase synthesis of irreversible human rhinovirus 3C protease inhibitors. Part 1: Optimization of tripeptides incorporating N-terminal amides

  摘要：

  The optimization of a series of irreversible human rhinovirus (HRV) 3C protease (3CP) inhibitors is described. These inhibitors are comprised of an L-Leu-L-Phe-L-Gln tripeptide containing an N-terminal amide moiety and a C-terminal ethyl propenoate Michael acceptor. Examination of approximately 500 compounds with varying N-terminal amides utilizing solid-phase synthesis and high-throughput assay techniques is described along with the solution phase preparation of several highly active molecules. A tripeptide Michael acceptor containing an N-terminal amide derived from 5-methylisoxazole-3-carboxylic acid is shown to exhibit potent, irreversible anti-3CP activity (k(obs)/[I] = 260,000 M-1 s(-1); type-14 3CP) and broad-spectrum antirhinoviral properties (average EC50 = 0.47 mu M against four different HRV serotypes). (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(99)00005-x
• 作为产物：
  描述：

  (E)-(S)-4-((S)-2-tert-Butoxycarbonylamino-3-phenyl-propionylamino)-6-(trityl-carbamoyl)-hex-2-enoic acid ethyl ester 在 N-甲基吗啉 、 盐酸 、 1-羟基苯并三唑 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 作用下， 反应 2.0h， 生成 (E)-(S)-4-((S)-2-{(S)-2-[((S)-2,5-Dihydro-1H-pyrrole-2-carbonyl)-amino]-4-methyl-pentanoylamino}-3-phenyl-propionylamino)-6-(trityl-carbamoyl)-hex-2-enoic acid ethyl ester
  参考文献：
  名称：

  Solid-phase synthesis of irreversible human rhinovirus 3C protease inhibitors. Part 1: Optimization of tripeptides incorporating N-terminal amides

  摘要：

  The optimization of a series of irreversible human rhinovirus (HRV) 3C protease (3CP) inhibitors is described. These inhibitors are comprised of an L-Leu-L-Phe-L-Gln tripeptide containing an N-terminal amide moiety and a C-terminal ethyl propenoate Michael acceptor. Examination of approximately 500 compounds with varying N-terminal amides utilizing solid-phase synthesis and high-throughput assay techniques is described along with the solution phase preparation of several highly active molecules. A tripeptide Michael acceptor containing an N-terminal amide derived from 5-methylisoxazole-3-carboxylic acid is shown to exhibit potent, irreversible anti-3CP activity (k(obs)/[I] = 260,000 M-1 s(-1); type-14 3CP) and broad-spectrum antirhinoviral properties (average EC50 = 0.47 mu M against four different HRV serotypes). (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(99)00005-x