2-{3-[N'-(2-benzyloxycarbonylamino-6-tertbutoxycarbonylaminohexanoyl)hydrazino]-4,4,4-trifluorobutyrylamino}-3-phenylpropionic acid methyl ester | 1123546-15-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 肽模拟物
• 英文名称: 2-{3-[N'-(2-benzyloxycarbonylamino-6-tertbutoxycarbonylaminohexanoyl)hydrazino]-4,4,4-trifluorobutyrylamino}-3-phenylpropionic acid methyl ester
• 英文别名: 2-{3-[N'-(6-benzyloxycarbonylamino-2-tert-butoxycarbonylaminohexanoyl)hydrazino]-4,4,4-trifluorobutyrylamino}-3-phenylpropionic acid methyl ester；methyl (2S)-3-phenyl-2-[[4,4,4-trifluoro-3-[2-[(2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-6-(phenylmethoxycarbonylamino)hexanoyl]hydrazinyl]butanoyl]amino]propanoate
• CAS: 1123546-15-5
• 化学式: C₃₃H₄₄F₃N₅O₈
• 分子量: 695.736
• InChiKey: BBUUWUDTRDUXPN-NPGWBMRXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  49
• 可旋转键数：
  21
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  173
• 氢给体数：
  5
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  2-{3-[N'-(2-benzyloxycarbonylamino-6-tertbutoxycarbonylaminohexanoyl)hydrazino]-4,4,4-trifluorobutyrylamino}-3-phenylpropionic acid methyl ester 在 palladium on carbon 、 氢气 作用下， 以 甲醇 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 生成 2-{3-[N'-(6-amino-2-tert-butoxycarbonylaminohexanoyl)hydrazino]-4,4,4-trifluorobutyrylamino}-3-phenylpropionic acid methyl ester
  参考文献：
  名称：

  Novel fluorinated pseudopeptides as proteasome inhibitors

  摘要：

  We have designed novel small inhibitors of rabbit 20S proteasome using a trifluoromethyl-beta-hydrazino acid scaffold. Structural variations influenced their inhibition of the three types of active sites. Proteasome inhibition at the micromolar level was selective, calpain I and cathepsin B were not inhibited. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.11.012
• 作为产物：
  描述：

  3-phenyl-2-(4,4,4-trifluoro-3-hydrazinobutyrylamino)propionic acid methyl ester trifluoroacetic acid salt 、 N-Boc-N'-Cbz-L-赖氨酸 在 1-羟基苯并三唑 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 68.0h， 以57%的产率得到2-{3-[N'-(2-benzyloxycarbonylamino-6-tertbutoxycarbonylaminohexanoyl)hydrazino]-4,4,4-trifluorobutyrylamino}-3-phenylpropionic acid methyl ester
  参考文献：
  名称：

  Novel fluorinated pseudopeptides as proteasome inhibitors

  摘要：

  We have designed novel small inhibitors of rabbit 20S proteasome using a trifluoromethyl-beta-hydrazino acid scaffold. Structural variations influenced their inhibition of the three types of active sites. Proteasome inhibition at the micromolar level was selective, calpain I and cathepsin B were not inhibited. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.11.012

文献信息

• Novel fluorinated pseudopeptides as proteasome inhibitors
  作者：Lucia Formicola、Xavier Maréchal、Nicolas Basse、Michelle Bouvier-Durand、Danièle Bonnet-Delpon、Thierry Milcent、Michèle Reboud-Ravaux、Sandrine Ongeri

  DOI：10.1016/j.bmcl.2008.11.012

  日期：2009.1

  We have designed novel small inhibitors of rabbit 20S proteasome using a trifluoromethyl-beta-hydrazino acid scaffold. Structural variations influenced their inhibition of the three types of active sites. Proteasome inhibition at the micromolar level was selective, calpain I and cathepsin B were not inhibited. (C) 2008 Elsevier Ltd. All rights reserved.