(2R,5'R)-3-[4-(2,6-dichlorobenzyloxy)phenyl]-2-(1-tert-butoxycarbonyl-6-oxo-1,7-diazaspiro[4.4]nonane-7-yl)propanoic acid | 797760-58-8

• 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,5'R)-3-[4-(2,6-dichlorobenzyloxy)phenyl]-2-(1-tert-butoxycarbonyl-6-oxo-1,7-diazaspiro[4.4]nonane-7-yl)propanoic acid
• 英文别名: (2R)-3-[4-[(2,6-dichlorophenyl)methoxy]phenyl]-2-[(5R)-1-[(2-methylpropan-2-yl)oxycarbonyl]-6-oxo-1,7-diazaspiro[4.4]nonan-7-yl]propanoic acid
• CAS: 797760-58-8
• 化学式: C₂₈H₃₂Cl₂N₂O₆
• 分子量: 563.478
• InChiKey: ZZKIIDCTKAGPQF-QDPGVEIFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  38
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  96.4
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  BOC-L-异亮氨酸 、 N-叔丁氧羰基-N'-甲苯磺酰基-L-精氨酸 、 (2R,5'R)-3-[4-(2,6-dichlorobenzyloxy)phenyl]-2-(1-tert-butoxycarbonyl-6-oxo-1,7-diazaspiro[4.4]nonane-7-yl)propanoic acid 、 alkaline earth salt of/the/ methylsulfuric acid 生成 H-Arg-Arg-[(S)-Pro-spiro-(R)-Tyr]-Ile-Leu-OH
  参考文献：
  名称：

  Evaluation of Lactam-Bridged Neurotensin Analogues Adjusting ψ(Pro¹⁰) Close to the Experimentally Derived Bioactive Conformation of NT(8−13)

  摘要：

  The neurotensin C-terminal hexapeptide, NT(8-13), which has been found to adopt a beta-strand-like conformation while bound to the NT1 receptor, was modified by the introduction of conformational constraints. Synthesis of the four stereoisomeric 4.4-spirolactams 1-4 and subsequent NT1 receptor binding studies showed that the restriction of Psi(Pro(10)) to approximately 130degrees leads to a more than 1000-fold increase of binding affinity for 1 (K-i = 12 nM) when compared to the more flexible analogue [NMeTyr(11)]NT(8-13).

  DOI：

  10.1021/jm049644y
• 作为产物：
  描述：

  (R)-methyl 2-allylpyrrolidine-2-carboxylate 在 sodium hydroxide 、 乙醇 、 臭氧 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 78.74h， 生成 (2R,5'R)-3-[4-(2,6-dichlorobenzyloxy)phenyl]-2-(1-tert-butoxycarbonyl-6-oxo-1,7-diazaspiro[4.4]nonane-7-yl)propanoic acid
  参考文献：
  名称：

  Evaluation of Lactam-Bridged Neurotensin Analogues Adjusting ψ(Pro¹⁰) Close to the Experimentally Derived Bioactive Conformation of NT(8−13)

  摘要：

  The neurotensin C-terminal hexapeptide, NT(8-13), which has been found to adopt a beta-strand-like conformation while bound to the NT1 receptor, was modified by the introduction of conformational constraints. Synthesis of the four stereoisomeric 4.4-spirolactams 1-4 and subsequent NT1 receptor binding studies showed that the restriction of Psi(Pro(10)) to approximately 130degrees leads to a more than 1000-fold increase of binding affinity for 1 (K-i = 12 nM) when compared to the more flexible analogue [NMeTyr(11)]NT(8-13).

  DOI：

  10.1021/jm049644y