(S)-N-[(R)-1-(2,4-Dimethoxy-benzyl)-3-isobutyl-2-oxo-azetidin-3-yl]-3-methyl-2-{(S)-2-[2-(3-phenoxy-phenyl)-acetylamino]-3-phenyl-propionylamino}-butyramide | 928824-19-5

• 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: (S)-N-[(R)-1-(2,4-Dimethoxy-benzyl)-3-isobutyl-2-oxo-azetidin-3-yl]-3-methyl-2-{(S)-2-[2-(3-phenoxy-phenyl)-acetylamino]-3-phenyl-propionylamino}-butyramide
• CAS: 928824-19-5
• 化学式: C₄₄H₅₂N₄O₇
• 分子量: 748.919
• InChiKey: HQIJTHOSKJESFE-REIIXUMVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.85
• 重原子数：
  55.0
• 可旋转键数：
  18.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  135.3
• 氢给体数：
  3.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  (S)-N-[(R)-1-(2,4-Dimethoxy-benzyl)-3-isobutyl-2-oxo-azetidin-3-yl]-3-methyl-2-{(S)-2-[2-(3-phenoxy-phenyl)-acetylamino]-3-phenyl-propionylamino}-butyramide 在 disodium hydrogenphosphate 、 dipotassium peroxodisulfate 作用下， 以 水 、 乙腈 为溶剂， 生成 (2S)-3-methyl-N-[(3R)-3-(2-methylpropyl)-2-oxoazetidin-3-yl]-2-[[(2S)-2-[[2-(3-phenoxyphenyl)acetyl]amino]-3-phenylpropanoyl]amino]butanamide
  参考文献：
  名称：

  Novel β-lactam derivatives: Potent and selective inhibitors of the chymotrypsin-like activity of the human 20S proteasome

  摘要：

  A series of beta-lactam derivatives has been designed and synthesized to inhibit the chymotrypsin-like activity of the human 20S proteasome. The most potent compounds of this new structural class of beta-subunit selective 20S proteasome inhibitors exhibit IC50 values in the low-nanomolar range and show good selectivity over the trypsin-like and post-glutamyl-peptide hydrolytic activities of the enzyme. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.10.047
• 作为产物：
  描述：

  <(2,4-dimethoxybenzyl)amino>acetonitrile 在 palladium on activated charcoal 氢气 、 O-(1,2-dihydro-2-oxo-1-pyridyl)-N,N,N',N'-tetramethyluronium tetrafluoroborate 、 N,N-二异丙基乙胺 、 lithium hexamethyldisilazane 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 生成 (S)-N-[(R)-1-(2,4-Dimethoxy-benzyl)-3-isobutyl-2-oxo-azetidin-3-yl]-3-methyl-2-{(S)-2-[2-(3-phenoxy-phenyl)-acetylamino]-3-phenyl-propionylamino}-butyramide
  参考文献：
  名称：

  Novel β-lactam derivatives: Potent and selective inhibitors of the chymotrypsin-like activity of the human 20S proteasome

  摘要：

  A series of beta-lactam derivatives has been designed and synthesized to inhibit the chymotrypsin-like activity of the human 20S proteasome. The most potent compounds of this new structural class of beta-subunit selective 20S proteasome inhibitors exhibit IC50 values in the low-nanomolar range and show good selectivity over the trypsin-like and post-glutamyl-peptide hydrolytic activities of the enzyme. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.10.047