(2R,3R,4S)-4-amino-3-hydroxy-N-[(2S)-1-[(2-hydroxy-4-methoxyphenyl)methylamino]-3-methyl-1-oxobutan-2-yl]-5-phenyl-2-[(3,4,5-trimethoxyphenyl)methylamino]pentanamide | 376644-36-9

• 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: (2R,3R,4S)-4-amino-3-hydroxy-N-[(2S)-1-[(2-hydroxy-4-methoxyphenyl)methylamino]-3-methyl-1-oxobutan-2-yl]-5-phenyl-2-[(3,4,5-trimethoxyphenyl)methylamino]pentanamide
• CAS: 376644-36-9
• 化学式: C₃₄H₄₆N₄O₈
• 分子量: 638.761
• InChiKey: LOPZGWOJLNQJND-HNEFVXLSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  46
• 可旋转键数：
  17
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  174
• 氢给体数：
  6
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  (2R,3R,4S)-4-amino-3-hydroxy-N-[(2S)-1-[(2-hydroxy-4-methoxyphenyl)methylamino]-3-methyl-1-oxobutan-2-yl]-5-phenyl-2-[(3,4,5-trimethoxyphenyl)methylamino]pentanamide 在 盐酸 、 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 1,4-二氧六环 、 N,N-二甲基乙酰胺 为溶剂， 生成 (2R,3R,4S)-4-((S)-2-Amino-3,3-dimethyl-butyrylamino)-3-hydroxy-5-phenyl-2-(3,4,5-trimethoxy-benzylamino)-pentanoic acid [(S)-1-(2-hydroxy-4-methoxy-benzylcarbamoyl)-2-methyl-propyl]-amide
  参考文献：
  名称：

  Structure-Based optimisation of 2-aminobenzylstatine derivatives: potent and selective inhibitors of the chymotrypsin-Like activity of the human 20S proteasome

  摘要：

  We have identified 2-aminobenzylstatine derivatives that inhibit non-covalently the chymotrypsin-like activity of the human 20S proteasome. A structure-based optimisation approach has allowed us to improve the potency of this structural class of proteasome inhibitors from micromolar to nanomolar level. The new derivatives showed good selectivity against the trypsin-like and post-glutamyl-peptide hydrolytic activities of this enzyme. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00178-6
• 作为产物：
  描述：

  N-Boc-L-苯丙氨醇 在 盐酸 、 lithium hydroxide 、 草酰氯 、 O-(1,2-dihydro-2-oxo-1-pyridyl)-N,N,N',N'-tetramethyluronium tetrafluoroborate 、 二甲基亚砜 、 三乙胺 、 N,N-二异丙基乙胺 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 生成 (2R,3R,4S)-4-amino-3-hydroxy-N-[(2S)-1-[(2-hydroxy-4-methoxyphenyl)methylamino]-3-methyl-1-oxobutan-2-yl]-5-phenyl-2-[(3,4,5-trimethoxyphenyl)methylamino]pentanamide
  参考文献：
  名称：

  Structure-Based optimisation of 2-aminobenzylstatine derivatives: potent and selective inhibitors of the chymotrypsin-Like activity of the human 20S proteasome

  摘要：

  We have identified 2-aminobenzylstatine derivatives that inhibit non-covalently the chymotrypsin-like activity of the human 20S proteasome. A structure-based optimisation approach has allowed us to improve the potency of this structural class of proteasome inhibitors from micromolar to nanomolar level. The new derivatives showed good selectivity against the trypsin-like and post-glutamyl-peptide hydrolytic activities of this enzyme. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00178-6