(E)-(S)-4-((S)-2-tert-Butoxycarbonylamino-3-phenyl-propionylamino)-6-(trityl-carbamoyl)-hex-2-enoic acid ethyl ester | 199006-04-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: (E)-(S)-4-((S)-2-tert-Butoxycarbonylamino-3-phenyl-propionylamino)-6-(trityl-carbamoyl)-hex-2-enoic acid ethyl ester
• CAS: 199006-04-7
• 化学式: C₄₂H₄₇N₃O₆
• 分子量: 689.852
• InChiKey: SBOPXGLOHHVKPH-GHJRQIQLSA-N

物化性质

• 沸点：
  897.9±65.0 °C(predicted)
• 密度：
  1.157±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.62
• 重原子数：
  51.0
• 可旋转键数：
  15.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  122.83
• 氢给体数：
  3.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  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 、 三异丙基硅烷 、 1-羟基苯并三唑 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 三乙胺 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 生成 (E)-(S)-6-Carbamoyl-4-((S)-2-{(S)-4-methyl-2-[(5-methyl-isoxazole-3-carbonyl)-amino]-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：

  (S,E)-ethyl 4-(tert-butoxycarbonylamino)-7-oxo-7-(tritylamino)-hept-2-enoate 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， 以 1,4-二氧六环 、 二氯甲烷 为溶剂， 反应 19.0h， 生成 (E)-(S)-4-((S)-2-tert-Butoxycarbonylamino-3-phenyl-propionylamino)-6-(trityl-carbamoyl)-hex-2-enoic acid ethyl ester
  参考文献：
  名称：

  Structure-based design of irreversible, tripeptidyl human rhinovirus 3C protease inhibitors containing N-methyl amino acids

  摘要：

  Tripeptide-derived molecules incorporating N-methyl amino acid residues and C-terminal Michael acceptor moieties were evaluated as irreversible inhibitors of the cysteine-containing human rhinovirus 3C protease (3CP). Such compounds displayed good 3CP inhibition activity (k(obs)/[I] up to 610,000 M(-1)s(-1)) and potent in vitro antiviral properties (EC50 approaching 0.03 mu M) when tested against HRV serotype-14. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(99)00368-6