2-[2-[Bis[2-[(2-methylpropan-2-yl)oxycarbonylamino]ethyl]amino]ethyl-[(2-methylpropan-2-yl)oxycarbonyl]amino]acetic acid | 191108-08-4

• 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: 2-[2-[Bis[2-[(2-methylpropan-2-yl)oxycarbonylamino]ethyl]amino]ethyl-[(2-methylpropan-2-yl)oxycarbonyl]amino]acetic acid
• 英文别名: 2-[2-[bis[2-[(2-methylpropan-2-yl)oxycarbonylamino]ethyl]amino]ethyl-[(2-methylpropan-2-yl)oxycarbonyl]amino]acetic acid
• CAS: 191108-08-4
• 化学式: C₂₃H₄₄N₄O₈
• 分子量: 504.624
• InChiKey: FKHKLPBJZXNELV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  35
• 可旋转键数：
  17
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  147
• 氢给体数：
  3
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  2-[2-[Bis[2-[(2-methylpropan-2-yl)oxycarbonylamino]ethyl]amino]ethyl-[(2-methylpropan-2-yl)oxycarbonyl]amino]acetic acid 在 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 N,N-二异丙基乙胺 、 三氟乙酸 作用下， 以 乙腈 为溶剂， 反应 2.25h， 生成 RPR-120528
  参考文献：
  名称：

  新型阳离子脂质用于DNA转移的合成，活性和结构-活性关系研究。

  摘要：

  我们已经设计并合成了用于基因传递的原始阳离子脂质。固体支持物上的合成方法可以轻松获得几何形状可变的不对称单官能聚胺结构单元。将这些多胺结构单元引入阳离子脂质中。为了优化新系列中的转染效率，我们通过引入可变长度脂质，脂质与阳离子部分之间的可变长度接头以及取代的接头进行了结构-活性关系研究。我们引入了使用阳离子脂质分子中的接头作为带有各种功能的侧基（侧链实体）的载体的概念，该方法通过引入由阳离子实体，其他脂质链，靶向基团组成的库进行评估 最后是用于细胞运输研究的分子探针若丹明和生物素。在体外在Hela癌，NIH3T3，CV1成纤维细胞上以及在刘易斯肺癌模型上在体内测定产物的转染活性。该系列产品显示出高转染活性。结果表明允许将靶向侧链部分引入阳离子脂质中。用该先导化合物证明了DNA /脂质复合物的主要理化特性。目前正在开发该系列中的部分产品用于临床前研究，标记的脂多胺可用于研究DNA /阳离子脂

  DOI：

  10.1021/jm9704964
• 作为产物：
  描述：

  2-(叔丁氧羰基氧亚氨基)-2-苯乙腈 在 sodium hydroxide 、 三乙酰氧基硼氢化钠 作用下， 生成 2-[2-[Bis[2-[(2-methylpropan-2-yl)oxycarbonylamino]ethyl]amino]ethyl-[(2-methylpropan-2-yl)oxycarbonyl]amino]acetic acid
  参考文献：
  名称：

  Toward Protein-Cleaving Catalytic Drugs: Artificial Protease Selective for Myoglobin

  摘要：

  A protein-cleaving catalyst highly selective for a disease-related protein can be used as a catalytic drug. As the first protein-cleaving catalyst selective for a protein substrate, a catalyst for myoglobin (Mb) was designed by attaching the Cu(II) or Co(III) complex of cyclen to a binding site searched by a combinatorial method using peptide nucleic acid monomers as building units. Various linkers were inserted between the catalytic Co(III) center and the binding site of the Mb-cleaving catalyst. Kinetic data revealed catalytic turnover of the Mb cleavage by the Cu(II) or Co(III) complex. MALDI-TOF MS revealed cleavage of the polypeptide backbone of Mb at selected positions. N-Terminal sequencing of the cleavage products identified the cleavage site and provided evidence for the hydrolytic nature of the Mb cleavage. Various chelating ligands were tested as the ligand for the Co(III) center of the Mb-cleaving catalyst. Among the nine chelating ligands examined, only cyclen and its triaza-monooxo analogue manifested catalytic activity. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(03)00216-5

文献信息

• One pot synthesis of unsymmetrically functionalized polyamines by a solid phase strategy starting from their symmetrical polyamine-counterparts
  作者：Gerardo Byk、Marc Frederic、Daniel Scherman

  DOI：10.1016/s0040-4039(97)00582-0

  日期：1997.5

  We have developed a solid phase methodology which allows a quick and easy access to a high number of mono-functionalized geometrically varied polyamines. The feasibility of the method was demonstrated by the unsymmetrical introduction of a single carboxylic acid functional group into differing symmetrical polyamines.

  我们已经开发出一种固相方法，可以快速，轻松地获得大量的单官能化几何变化的多胺。通过将单个羧酸官能团不对称地引入不同的对称多胺中，证明了该方法的可行性。
• Toward Protein-Cleaving Catalytic Drugs: Artificial Protease Selective for Myoglobin
  作者：Joong Won Jeon、Sang Jun Son、Chang Eun Yoo、In Seok Hong、Junghun Suh

  DOI：10.1016/s0968-0896(03)00216-5

  日期：2003.7

  A protein-cleaving catalyst highly selective for a disease-related protein can be used as a catalytic drug. As the first protein-cleaving catalyst selective for a protein substrate, a catalyst for myoglobin (Mb) was designed by attaching the Cu(II) or Co(III) complex of cyclen to a binding site searched by a combinatorial method using peptide nucleic acid monomers as building units. Various linkers were inserted between the catalytic Co(III) center and the binding site of the Mb-cleaving catalyst. Kinetic data revealed catalytic turnover of the Mb cleavage by the Cu(II) or Co(III) complex. MALDI-TOF MS revealed cleavage of the polypeptide backbone of Mb at selected positions. N-Terminal sequencing of the cleavage products identified the cleavage site and provided evidence for the hydrolytic nature of the Mb cleavage. Various chelating ligands were tested as the ligand for the Co(III) center of the Mb-cleaving catalyst. Among the nine chelating ligands examined, only cyclen and its triaza-monooxo analogue manifested catalytic activity. (C) 2003 Elsevier Science Ltd. All rights reserved.
• Synthesis, Activity, and Structure−Activity Relationship Studies of Novel Cationic Lipids for DNA Transfer
  作者：Gerardo Byk、Catherine Dubertret、Virginie Escriou、Marc Frederic、Gabrielle Jaslin、Ravi Rangara、Bruno Pitard、Joel Crouzet、Pierre Wils、Bertrand Schwartz、Daniel Scherman

  DOI：10.1021/jm9704964

  日期：1998.1.1

  synthetic method on solid support allowed easy access to unsymmetrically monofunctionalized polyamine building blocks of variable geometries. These polyamine building blocks were introduced into cationic lipids. To optimize the transfection efficiency in the novel series, we have carried out structure-activity relationship studies by introduction of variable-length lipids, of variable-length linkers between

  我们已经设计并合成了用于基因传递的原始阳离子脂质。固体支持物上的合成方法可以轻松获得几何形状可变的不对称单官能聚胺结构单元。将这些多胺结构单元引入阳离子脂质中。为了优化新系列中的转染效率，我们通过引入可变长度脂质，脂质与阳离子部分之间的可变长度接头以及取代的接头进行了结构-活性关系研究。我们引入了使用阳离子脂质分子中的接头作为带有各种功能的侧基（侧链实体）的载体的概念，该方法通过引入由阳离子实体，其他脂质链，靶向基团组成的库进行评估 最后是用于细胞运输研究的分子探针若丹明和生物素。在体外在Hela癌，NIH3T3，CV1成纤维细胞上以及在刘易斯肺癌模型上在体内测定产物的转染活性。该系列产品显示出高转染活性。结果表明允许将靶向侧链部分引入阳离子脂质中。用该先导化合物证明了DNA /脂质复合物的主要理化特性。目前正在开发该系列中的部分产品用于临床前研究，标记的脂多胺可用于研究DNA /阳离子脂