[(S)-1-((S)-1-{(E)-(S)-3-Dimethylcarbamoyl-1-[2-(trityl-carbamoyl)-ethyl]-allylcarbamoyl}-2-phenyl-ethylcarbamoyl)-3-methyl-butyl]-carbamic acid benzyl ester | 199005-84-0

• 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: [(S)-1-((S)-1-{(E)-(S)-3-Dimethylcarbamoyl-1-[2-(trityl-carbamoyl)-ethyl]-allylcarbamoyl}-2-phenyl-ethylcarbamoyl)-3-methyl-butyl]-carbamic acid benzyl ester
• 英文别名: benzyl N-[(2S)-1-[[(2S)-1-[[(E,4S)-1-(dimethylamino)-1,7-dioxo-7-(tritylamino)hept-2-en-4-yl]amino]-1-oxo-3-phenylpropan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]carbamate
• CAS: 199005-84-0
• 化学式: C₅₁H₅₇N₅O₆
• 分子量: 836.043
• InChiKey: CZHNMRVYTFGXTB-IGNYUCETSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.9
• 重原子数：
  62
• 可旋转键数：
  21
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  146
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  [(S)-1-((S)-1-{(E)-(S)-3-Dimethylcarbamoyl-1-[2-(trityl-carbamoyl)-ethyl]-allylcarbamoyl}-2-phenyl-ethylcarbamoyl)-3-methyl-butyl]-carbamic acid benzyl 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 0.33h， 生成 benzyl N-[(1S)-1-[[(1S)-2-[[(E,1S)-1-(3-amino-3-oxo-propyl)-4-(dimethylamino)-4-oxo-but-2-enyl]amino]-1-benzyl-2-oxo-ethyl]carbamoyl]-3-methyl-butyl]carbamate
  参考文献：
  名称：

  Structure-Based Design, Synthesis, and Biological Evaluation of Irreversible Human Rhinovirus 3C Protease Inhibitors. 1. Michael Acceptor Structure−Activity Studies

  摘要：

  The structure-based design, chemical synthesis, and biological evaluation of peptide-derived human rhinovirus (HRV) 3C protease (3CP) inhibitors are described. These compounds incorporate various Michael acceptor moieties and are shown to irreversibly bind to HRV serotype 14 3CP with inhibition activities (k(obs)/[I]) ranging from 100 to 600 000 M-1 s(-1). These inhibitors are also shown to exhibit antiviral activity when tested against HRV-14-infected H1-HeLa cells with EC50's approaching 0.50 mu M. Extensive structure-activity relationships developed by Michael acceptor alteration are reported along with the evaluation of several compounds against HRV serotypes other than 14. A 2.0 Angstrom crystal structure of a peptide-derived inhibitor complexed with HRV-2 3CP is also detailed.

  DOI：

  10.1021/jm980068d
• 作为产物：
  描述：

  Boc-Gln(Trt)-H 在 N-甲基吗啉 、 盐酸 、 sodium hydroxide 、 sodium hexamethyldisilazane 、 1-羟基苯并三唑一水物 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 1,4-二氧六环 、 乙醇 、 二氯甲烷 为溶剂， 反应 57.0h， 生成 [(S)-1-((S)-1-{(E)-(S)-3-Dimethylcarbamoyl-1-[2-(trityl-carbamoyl)-ethyl]-allylcarbamoyl}-2-phenyl-ethylcarbamoyl)-3-methyl-butyl]-carbamic acid benzyl ester
  参考文献：
  名称：

  Structure-Based Design, Synthesis, and Biological Evaluation of Irreversible Human Rhinovirus 3C Protease Inhibitors. 1. Michael Acceptor Structure−Activity Studies

  摘要：

  The structure-based design, chemical synthesis, and biological evaluation of peptide-derived human rhinovirus (HRV) 3C protease (3CP) inhibitors are described. These compounds incorporate various Michael acceptor moieties and are shown to irreversibly bind to HRV serotype 14 3CP with inhibition activities (k(obs)/[I]) ranging from 100 to 600 000 M-1 s(-1). These inhibitors are also shown to exhibit antiviral activity when tested against HRV-14-infected H1-HeLa cells with EC50's approaching 0.50 mu M. Extensive structure-activity relationships developed by Michael acceptor alteration are reported along with the evaluation of several compounds against HRV serotypes other than 14. A 2.0 Angstrom crystal structure of a peptide-derived inhibitor complexed with HRV-2 3CP is also detailed.

  DOI：

  10.1021/jm980068d