{[(benzyloxy)carbonyl]amino}-4-[(tertbutoxycarbonyl)amino]butane | 62146-59-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: {[(benzyloxy)carbonyl]amino}-4-[(tertbutoxycarbonyl)amino]butane
• 英文别名: Z-NH-(CH2)4-NH-Boc；benzyl N-[4-[(2-methylpropan-2-yl)oxycarbonylamino]butyl]carbamate
• CAS: 62146-59-2
• 化学式: C₁₇H₂₆N₂O₄
• 分子量: 322.404
• InChiKey: GUVSJTCSUOCQHO-UHFFFAOYSA-N

物化性质

• 沸点：
  487.4±38.0 °C(Predicted)
• 密度：
  1.091±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  23
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  76.7
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  {[(benzyloxy)carbonyl]amino}-4-[(tertbutoxycarbonyl)amino]butane 在 palladium on activated charcoal 、 镍 sodium hydroxide 、 氢气 作用下， 以 甲醇 、 乙醇 、 水 为溶剂， 25.0 ℃ 、101.33 kPa 条件下， 反应 4.0h， 生成 tert-butyl 4-(3-aminopropylamino)butylcarbamate
  参考文献：
  名称：

  Arasujo, M. Joso S. M. P.; Ragnarsson, Ulf; Trigo, M. Joaquina S. A. Amaral, Journal of Chemical Research, Miniprint, 1996, # 8, p. 2143 - 2161

  摘要：

  DOI：
• 作为产物：
  描述：

  4-(N-叔丁氧羰基氨基)-1-丁醇 在 potassium dihydrogenphosphate 、 三苯基膦 、 锌 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 生成 {[(benzyloxy)carbonyl]amino}-4-[(tertbutoxycarbonyl)amino]butane
  参考文献：
  名称：

  Arasujo, M. Joso S. M. P.; Ragnarsson, Ulf; Trigo, M. Joaquina S. A. Amaral, Journal of Chemical Research, Miniprint, 1996, # 8, p. 2143 - 2161

  摘要：

  DOI：

文献信息

• PEPTOID-BASED CHELATING LIGANDS FOR SELECTIVE METAL CHELATION
  申请人：Triad National Security, LLC

  公开号：US20200109173A1

  公开（公告）日：2020-04-09

  The present disclosure provides peptoid-based chelating ligands, corresponding cyclic peptoids, and methods of making thereof. Functional groups may be tailored for high metal binding affinity and selectivity. The side chains of a cyclic peptoid according to the present disclosure may be selected based on, for example, high affinity for actinide or other metal ions, selectivity for actinide or other metal ions, the ability to recover a metal once it is bound to the peptoid, and whether the overall peptoid should be hydrophobic or hydrophilic. Unlike siderophores, peptoid-based chelating ligands of the present disclosure are not readily hydrolyzed under physiological conditions. Therefore, peptoid-based chelating ligands may be, for example, used to treat actinide (e.g., iron and lead) poisoning in vivo. Moreover, peptoid-based chelating ligands of the present disclosure may be used for medical imaging, chelation therapy, drug delivery, and separation technologies, for example.

  本公开提供基于肽酰胺的螯合配体、相应的环状肽酰胺及其制备方法。功能基团可以根据高金属结合亲和力和选择性进行定制。根据本公开的环状肽酰胺的侧链可以根据，例如，对锕系元素或其他金属离子的高亲和力、对锕系元素或其他金属离子的选择性、一旦金属与肽酰胺结合后是否能够回收金属，以及整体肽酰胺是疏水性还是亲水性来进行选择。与铁载体不同，本公开的基于肽酰胺的螯合配体在生理条件下不容易水解。因此，基于肽酰胺的螯合配体可以用于治疗体内的锕系元素（例如铁和铅）中毒。此外，本公开的基于肽酰胺的螯合配体可以用于医学成像、螯合疗法、药物输送和分离技术等领域。
• Practical, convergent total synthesis of polyamine amide spider toxin NSTX-3
  作者：Ian S Blagbrough、Eduardo Moya、Steven P Walford

  DOI：10.1016/0040-4039(95)02238-4

  日期：1996.1

  A practical, total synthesis of polyamine amide spider toxin NSTX-3, a potent glutamate receptor antagonist with potential as a neuroprotective agent, is reported. The unsymmetrical polyamine motiety was built by a conjugate addition to afford putreamine and regioselective acylation of L-asparaginyl-cadaverine.

  报道了一种实用的，全合成的多胺酰胺蜘蛛毒素NSTX-3，一种有效的谷氨酸受体拮抗剂，具有潜在的神经保护作用。通过共轭加成来建立不对称的多胺部分，以提供L-天冬酰胺基-尸胺的腐胺和区域选择性酰化。
• Fuchs,S.; Voelter,W., Zeitschrift fur Naturforschung, Teil B: Anorganische Chemie, Organische Chemie, 1976, vol. 31, p. 1410 - 1415
  作者：Fuchs,S.、Voelter,W.

  DOI：——

  日期：——
• Degradable PEG-folate coated poly(DMAEA-co-BA)phosphazene-based polyplexes exhibit receptor-specific gene expression
  作者：J. Luten、M.J. van Steenbergen、M.C. Lok、A.M. de Graaff、C.F. van Nostrum、H. Talsma、W.E. Hennink

  DOI：10.1016/j.ejps.2007.12.003

  日期：2008.3

  A new cationic biodegradable polyphosphazene was developed, bearing both pendant primary and tertiary amine side groups, poly(2-dimethylaminoethylamine-codiaminobutane)phosphazene (poly(DMAEA-co-BA)phosphazene). PEG and PEG-folate were coupled to polyplexes based on this poly(DMAEA-co-BA)phosphazene, leading to small (size 100 and 120nm, respectively) and almost neutral particles. in vitro tissue culture experiments showed a low cytotoxicity of both uncoated and coated polyplexes. However, the PEG coated polyplexes showed a 2-fold lower transfection activity in OVCAR 3 cells as compared to the uncoated polyplexes. On the other hand, the PEG-folate coated polyplexes had a 3-fold higher transfection. than the PEGylated polyplexes. When free folate was added to the transfection medium, only the transfection activity of the targeted polyplexes was reduced, indicating internalization of the targeted PEG polyplexes via the folate receptor. Confocal laser scanning microscopy confirmed a lower binding and uptake of the PEGylated polyplexes by OVCAR-3 cells when compared to uncoated and folate-PEGylated polyplexes. While uncoated polyplexes induced aggregation of erythrocytes at polymer concentrations of 0.09 mu g/mL, the PEGylated systems could be incubated at ten times higher concentration before aggregation occurred indicating excellent shielding of the surface charge of the polyplexes by grafting of PEG. In conclusion, the targeted delivery of poly(DMAEA-co-BA)phosphazene bases polyplexes and their improved compatibility with erythrocytes makes them interesting for in vivo applications. (C) 2008 Published by Elsevier B.V.
• Structure−Activity Relationship Study on a Simple Cationic Peptide Motif for Cellular Delivery of Antisense Peptide Nucleic Acid
  作者：Klaus Albertshofer、Andrew M. Siwkowski、Edward V. Wancewicz、Christine C. Esau、Tanya Watanabe、Kenji C. Nishihara、Garth A. Kinberger、Leila Malik、Anne B. Eldrup、Muthiah Manoharan、Richard S. Geary、Brett P. Monia、Eric E. Swayze、Richard H. Griffey、C. Frank Bennett、Martin A. Maier

  DOI：10.1021/jm050490b

  日期：2005.10.1

  Improving cellular uptake and biodistribution remains one of the major obstacles for a successful and broad application of peptide nucleic acids (PNAs) as antisense therapeutics. Recently, we reported the identification and functional characterization of an antisense PNA, which redirects splicing of murine CD40 pre-mRNA. In this context, it was discovered that a simple octa(L-lysine) peptide covalently linked to the PNA is capable of promoting free uptake of the conjugate into BCL1 cells as well as primary murine macrophages. On the basis of this peptide motif, the present study aimed at identifying the structural features, which define effective peptide carriers for cellular delivery of PNA. While the structure-activity relationship study revealed some clear correlations, only a few modifications actually led to an overall improvement as compared to the parent octa(L-lysine) conjugate. In a preliminary PK/tissue distribution study in healthy mice, the parent conjugate exhibited relatively broad tissue distribution and only modest elimination via excretion within the time frame of the study.