(S)-2-[(S)-2-amino-3-(2,3,4-trimethoxy-phenyl)-propionylamino]-N-((R)-3-isobutyl-2-oxo-azetidin-3-yl)-3-methyl-butyramide | 928824-30-0

• 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: (S)-2-[(S)-2-amino-3-(2,3,4-trimethoxy-phenyl)-propionylamino]-N-((R)-3-isobutyl-2-oxo-azetidin-3-yl)-3-methyl-butyramide
• CAS: 928824-30-0
• 化学式: C₂₄H₃₈N₄O₆
• 分子量: 478.589
• InChiKey: JWZSVCLDCFLZDV-READRUSDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.75
• 重原子数：
  34.0
• 可旋转键数：
  12.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  141.01
• 氢给体数：
  4.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  (S)-2-[(S)-2-amino-3-(2,3,4-trimethoxy-phenyl)-propionylamino]-N-((R)-3-isobutyl-2-oxo-azetidin-3-yl)-3-methyl-butyramide 、 3-苯氧基苯乙酸 在 O-(1,2-dihydro-2-oxo-1-pyridyl)-N,N,N',N'-tetramethyluronium tetrafluoroborate 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 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-(2,3,4-trimethoxyphenyl)propanoyl]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：

  [(R)-1-(2,4-Dimethoxy-benzyl)-3-isobutyl-2-oxo-azetidin-3-yl]-carbamic acid benzyl ester 在 palladium on activated charcoal disodium hydrogenphosphate 、 dipotassium peroxodisulfate 、 氢气 、 O-(1,2-dihydro-2-oxo-1-pyridyl)-N,N,N',N'-tetramethyluronium tetrafluoroborate 、 N,N-二异丙基乙胺 作用下， 以 甲醇 、 水 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 生成 (S)-2-[(S)-2-amino-3-(2,3,4-trimethoxy-phenyl)-propionylamino]-N-((R)-3-isobutyl-2-oxo-azetidin-3-yl)-3-methyl-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