benzyl N-[(2S)-1-[[(2S)-4-methylsulfanyl-1-oxobutan-2-yl]amino]-1-oxo-3-phenylpropan-2-yl]carbamate | 185799-74-0

• 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: benzyl N-[(2S)-1-[[(2S)-4-methylsulfanyl-1-oxobutan-2-yl]amino]-1-oxo-3-phenylpropan-2-yl]carbamate
• CAS: 185799-74-0
• 化学式: C₂₂H₂₆N₂O₄S
• 分子量: 414.525
• InChiKey: ACFCLOFCDBIRRQ-PMACEKPBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  29
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  110
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  benzyl N-[(2S)-1-[[(2S)-4-methylsulfanyl-1-oxobutan-2-yl]amino]-1-oxo-3-phenylpropan-2-yl]carbamate 在 Oxone 作用下， 以 甲醇 、 水 为溶剂， 以85%的产率得到LY 338387
  参考文献：
  名称：

  Small peptidic aldehyde inhibitors of human rhinovirus 3C protease

  摘要：

  Small peptide aldehydes were designed to mimic the preferred substrate requirements for the human rhinovirus 3C protease. Di- and tripeptide aldehydes containing a methionine sulfone as a P-1 surrogate for glutamine show low micromolar enzyme inhibitory and antiviral tissue culture activity. LY338387, obtained in a short and efficient synthesis, appears to validate the protease as a therapeutic target. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/s0960-894x(96)00537-9
• 作为产物：
  描述：

  L-蛋氨醇 在 三氧化硫吡啶 、 三乙胺 、 N,N'-羰基二咪唑 作用下， 以 四氢呋喃 、 二甲基亚砜 为溶剂， 反应 0.17h， 生成 benzyl N-[(2S)-1-[[(2S)-4-methylsulfanyl-1-oxobutan-2-yl]amino]-1-oxo-3-phenylpropan-2-yl]carbamate
  参考文献：
  名称：

  Small peptidic aldehyde inhibitors of human rhinovirus 3C protease

  摘要：

  Small peptide aldehydes were designed to mimic the preferred substrate requirements for the human rhinovirus 3C protease. Di- and tripeptide aldehydes containing a methionine sulfone as a P-1 surrogate for glutamine show low micromolar enzyme inhibitory and antiviral tissue culture activity. LY338387, obtained in a short and efficient synthesis, appears to validate the protease as a therapeutic target. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/s0960-894x(96)00537-9

文献信息

• Small peptidic aldehyde inhibitors of human rhinovirus 3C protease
  作者：Timothy A. Shepherd、Gregory A. Cox、Emma McKinney、Joseph Tang、Mark Wakulchik、Ronald E. Zimmerman、Elcira C. Villarreal

  DOI：10.1016/s0960-894x(96)00537-9

  日期：1996.12

  Small peptide aldehydes were designed to mimic the preferred substrate requirements for the human rhinovirus 3C protease. Di- and tripeptide aldehydes containing a methionine sulfone as a P-1 surrogate for glutamine show low micromolar enzyme inhibitory and antiviral tissue culture activity. LY338387, obtained in a short and efficient synthesis, appears to validate the protease as a therapeutic target. Copyright (C) 1996 Elsevier Science Ltd