4-[3,3-dimethyl-2-(2-naphthalen-1-yl-acetylamino)-butyrylamino]-3-hydroxy-2-(4-methoxy-benzylamino)-5-phenyl-pentanoic acid [1-(2-hydroxy-4-methoxy-benzyl-carbamoyl)-2-methyl-propyl]-amide

• 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: 4-[3,3-dimethyl-2-(2-naphthalen-1-yl-acetylamino)-butyrylamino]-3-hydroxy-2-(4-methoxy-benzylamino)-5-phenyl-pentanoic acid [1-(2-hydroxy-4-methoxy-benzyl-carbamoyl)-2-methyl-propyl]-amide
• 英文别名: (2S)-N-[(1S,2R,3R)-1-benzyl-2-hydroxy-4-[[(1S)-1-[(2-hydroxy-4-methoxy-phenyl)methylcarbamoyl]-2-methyl-propyl]amino]-3-[(4-methoxyphenyl)methylamino]-4-oxo-butyl]-3,3-dimethyl-2-[[2-(1-naphthyl)acetyl]amino]butanamide；(2S)-N-[(2S,3R,4R)-3-hydroxy-5-[[(2S)-1-[(2-hydroxy-4-methoxyphenyl)methylamino]-3-methyl-1-oxobutan-2-yl]amino]-4-[(4-methoxyphenyl)methylamino]-5-oxo-1-phenylpentan-2-yl]-3,3-dimethyl-2-[(2-naphthalen-1-ylacetyl)amino]butanamide
• 化学式: C₅₀H₆₁N₅O₈
• 分子量: 860.063
• InChiKey: JAKXWGBSDNJRIC-BZDBZJANSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.7
• 重原子数：
  63
• 可旋转键数：
  21
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  187
• 氢给体数：
  7
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  N-Boc-L-苯丙氨醛 在 盐酸 、 lithium hydroxide 、 2,4-滴二甲胺盐 、 O-(1,2-dihydro-2-oxo-1-pyridyl)-N,N,N',N'-tetramethyluronium tetrafluoroborate 、 N,N-二异丙基乙胺 、 间氯过氧苯甲酸 、 三氟乙酸 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 4-[3,3-dimethyl-2-(2-naphthalen-1-yl-acetylamino)-butyrylamino]-3-hydroxy-2-(4-methoxy-benzylamino)-5-phenyl-pentanoic acid [1-(2-hydroxy-4-methoxy-benzyl-carbamoyl)-2-methyl-propyl]-amide
  参考文献：
  名称：

  A New Structural Class of Selective and Non-covalent Inhibitors of the Chymotrypsin-like Activity of the 20S Proteasome

  摘要：

  We describe the identification and in vitro characterization of a series of 2-aminobenzylstatine derivatives that inhibit non-covalently the chymotrypsin-like activity of the 20S proteasome. Our initial SAR data demonstrate that the 2-aminobenzylstatine core structure can effectively serve as the basis for designing potent, selective and non-covalent inhibitors of the chymotrypsin-like activity of the 20S proteasome. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(01)00205-0

文献信息

• Structure-Based optimisation of 2-aminobenzylstatine derivatives: potent and selective inhibitors of the chymotrypsin-Like activity of the human 20S proteasome
  作者：Pascal Furet、Patricia Imbach、Peter Fuerst、Marc Lang、Maria Noorani、Johann Zimmermann、Carlos Garcı́a-Echeverrı́a

  DOI：10.1016/s0960-894x(02)00178-6

  日期：2002.5

  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.
• A New Structural Class of Selective and Non-covalent Inhibitors of the Chymotrypsin-like Activity of the 20S Proteasome
  作者：C Garcı́a-Echeverrı́a、P Imbach、D France、P Fürst、M Lang、M Noorani、D Scholz、J Zimmermann、P Furet

  DOI：10.1016/s0960-894x(01)00205-0

  日期：2001.5

  We describe the identification and in vitro characterization of a series of 2-aminobenzylstatine derivatives that inhibit non-covalently the chymotrypsin-like activity of the 20S proteasome. Our initial SAR data demonstrate that the 2-aminobenzylstatine core structure can effectively serve as the basis for designing potent, selective and non-covalent inhibitors of the chymotrypsin-like activity of the 20S proteasome. (C) 2001 Elsevier Science Ltd. All rights reserved.