4-(氨基氧基)-1-丁酰胺 | 69182-55-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 4-(氨基氧基)-1-丁酰胺
• 英文名称: 4-(aminooxy)butylamine
• 英文别名: O-(4-aminobutyl)hydroxylamine；4-(aminooxy)butanamine；AOBA；1-Aminooxy-4-aminobutane
• CAS: 69182-55-4
• 化学式: C₄H₁₂N₂O
• mdl: MFCD14584443
• 分子量: 104.152
• InChiKey: BRMYHTNDDMKDGY-UHFFFAOYSA-N

物化性质

• 沸点：
  216.3±23.0 °C(Predicted)
• 密度：
  0.961±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  7
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  61.3
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-(氨基氧基)-1-丁酰胺 、 洋地黄毒苷双氧苷1-（1-甲基-2-氧乙氧基）-3-氧丙基）醚 在 sodium acetate 作用下， 以 甲醇 、 水 为溶剂， 生成
  参考文献：
  名称：

  Syntheses of europium-labeled digoxin derivatives and their use in time-resolved fluoroimmunoassay

  摘要：

  A simple and efficient method of derivatizing and labeling the terminal sugar ring of digoxin (and other steroid glycosides) is described. The terminal sugar ring was oxidized by periodate to dialdehyde, followed by a reaction with the aminooxy group of a heterobifunctional spacer reagent. Usually, reductive amination is needed to stabilize the Schiff base-type compounds produced in reactions between amino and aldehyde groups. Here the oxime compounds produced are stable wherefore the reductive amination step can be avoided and the reaction gives high yields without significant side reactions. After characterization the digoxin dioxime derivatives formed were labeled with europium chelates. These labeled digoxin derivatives bearing one or two europium-containing chelates, coupled via different spacers, were purified and tested in a competitive time-resolved fluoroimmunoassay. Several digoxin-specific monoclonal antibodies were also tested to determine the most suitable antibody-tracer combination, which was then employed to develop a simple competitive time-resolved fluoroimmunoassay for digoxin.

  DOI：

  10.1016/0039-128x(94)90060-4
• 作为产物：
  描述：

  Carbamic acid, (4-氨基丁氧基)-, 1,1-二甲基乙酯 (9CI) 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以99%的产率得到4-(氨基氧基)-1-丁酰胺
  参考文献：
  名称：

  用于肿瘤定向药物递送的靶向 αvβ3 整合素的 RGD 拟肽-紫杉醇偶联物的设计和合成

  摘要：

  对 αvβ3 整联蛋白具有纳摩尔亲和力的基于 1,2,3-三唑的 RGD 肽模拟物通过肟异双功能接头与有效的抗有丝分裂紫杉醇偶联。相对于不表达αvβ3的MCF7细胞，所得构建体保持了与αvβ3整联蛋白的纳摩尔结合浓度，并且在对高度表达αvβ3的U87MG癌细胞的细胞毒性方面显示出11倍的选择性，表明具有良好的癌细胞靶向能力。1 设计 2 逆合成 3 合成 4 固相受体结合试验 5 细胞细胞毒性试验 6 代谢稳定性试验 7 结论

  DOI：

  10.1055/s-0036-1590898

文献信息

• 17β-<i>O</i>-Aminoalkyloximes of 5β-Androstane-3β,14β-diol with Digitalis-like Activity:  Synthesis, Cardiotonic Activity, Structure−Activity Relationships, and Molecular Modeling of the Na⁺,K⁺-ATPase Receptor
  作者：Alberto Cerri、Nicoletta Almirante、Paolo Barassi、Alessandra Benicchio、Giorgio Fedrizzi、Patrizia Ferrari、Rosella Micheletti、Luisa Quadri、Enzio Ragg、Roberto Rossi、Marco Santagostino、Antonio Schiavone、Fulvio Serra、Maria Pia Zappavigna、Piero Melloni

  DOI：10.1021/jm990627w

  日期：2000.6.1

  with a 17-aminoalkoxyiminoalkyl or -alkenyl substituent was synthesized and evaluated for inhibition of Na(+),K(+)-ATPase and for inotropic activity. The highest inhibition was found with compounds having the substituent in configuration 17beta and the amino group at a distance of 6 or 7 bonds from C(17) of the digitoxigenin skeleton. The presence of the oxime function strengthens the interaction with

  合成了一系列具有17-氨基烷氧基亚氨基烷基或-烯基取代基的洋地黄样化合物，并评估了其对Na（+），K（+）-ATPase的抑制作用和正性肌力活性。在具有构型17beta的取代基且氨基距洋地黄毒苷骨架的C（17）6或7个键的距离处发现具有最高的抑制作用。肟功能的存在加强了与受体的相互作用，如果α，β-不饱和的话，则更有效，从而模仿了天然洋地黄化合物中不饱和内酯的电子状态。活性最高的化合物显示Na（+），K（+）-ATPase抑制能力（IC（50））比标准地黄毒苷原和地高辛高17-25倍，而正性肌力（EC（50））高3-11倍。孤立的豚鼠左心房。这些特征得到了分子模型的支持，该分子模型暗示了上述基团与Na（+），K（+）-ATPase的H1-H2域中特定氨基酸残基的可能相互作用。一些互动是文献中已经描述的经典互动；发现了碱性基团与Cys138的新的非常强的相互作用，为设计与受体此区域相互作用的
• Synthesis and Inotropic Activity of 1-(<i>O</i>-Aminoalkyloximes) of Perhydroindene Derivatives as Simplified Digitalis-like Compounds Acting on the Na⁺,K⁺-ATPase
  作者：Alberto Cerri、Nicoletta Almirante、Paolo Barassi、Alessandra Benicchio、Sergio De Munari、Giuseppe Marazzi、Isabella Molinari、Fulvio Serra、Piero Melloni

  DOI：10.1021/jm011001k

  日期：2002.1.1

  A series of 5-substituted (3aS,7aR)-7a-methylperhydroinden-3a-ol derivatives bearing a 1(S)(omega-aminoalkoxy)iminoalkyl or -alkenyl substituent was synthesized, starting from the Hajos-Parrish ketol 47, as simplified analogues of very potent 17beta-aminoalkyloximes with digitalis skeleton, previously reported. The target compounds were evaluated in vitro for displacement of the specific [H-3]ouabain binding from the dog kidney Na+,K+-ATPase receptor. Some of them revealed IC50 values in the micromolar range. The most active compounds possess a cyclohexyl group in the 5(S) position and in position 1(S) the same aminoalkyloxime groups already reported for the digitoxigenin-like series in position 17beta. Although the ring conformation of these derivatives was comparable to that of uzarigenin, the binding affinities of the most active ones were 4/8-fold lower in comparison to that standard, Three compounds among those with the highest affinities were assayed in vitro for their inotropic activity on an electrically driven guinea pig left atrium and were found to be less potent than both digoxin, the most widely used inotropic agent, and the corresponding digitalis 17beta-aminoalkyloximes.
• Use of N-protected aminoalkoxyamines in synthesis of aminooxy adsorbents using BrCN
  作者：A. A. Nedospasov、R. M. Khomutov

  DOI：10.1007/bf00946544

  日期：1978.10
• Syntheses of europium-labeled digoxin derivatives and their use in time-resolved fluoroimmunoassay
  作者：Heikki Mikola、Elisabeth Hedlöf

  DOI：10.1016/0039-128x(94)90060-4

  日期：1994.8

  A simple and efficient method of derivatizing and labeling the terminal sugar ring of digoxin (and other steroid glycosides) is described. The terminal sugar ring was oxidized by periodate to dialdehyde, followed by a reaction with the aminooxy group of a heterobifunctional spacer reagent. Usually, reductive amination is needed to stabilize the Schiff base-type compounds produced in reactions between amino and aldehyde groups. Here the oxime compounds produced are stable wherefore the reductive amination step can be avoided and the reaction gives high yields without significant side reactions. After characterization the digoxin dioxime derivatives formed were labeled with europium chelates. These labeled digoxin derivatives bearing one or two europium-containing chelates, coupled via different spacers, were purified and tested in a competitive time-resolved fluoroimmunoassay. Several digoxin-specific monoclonal antibodies were also tested to determine the most suitable antibody-tracer combination, which was then employed to develop a simple competitive time-resolved fluoroimmunoassay for digoxin.
• Design and Synthesis of an RGD Peptidomimetic-Paclitaxel Conjugate Targeting αvβ3 Integrin for Tumour-Directed Drug Delivery
  作者：Monica Piras、Alexandra Andriu、Andrea Testa、Paul Wienecke、Ian Fleming、Matteo Zanda

  DOI：10.1055/s-0036-1590898

  日期：2017.12

  A 1,2,3-triazole-based RGD peptidomimetic having nanomolar affinity for αvβ3 integrin was conjugated to the potent antimitotic paclitaxel via an oxime heterobifunctional linker. The resulting construct maintained nanomolar binding concentration to αvβ3 integrin and showed 11-fold selectivity in terms of cytotoxicity towards highly αvβ3 expressing U87MG cancer cells relative to non αvβ3 expressing MCF7

  对 αvβ3 整联蛋白具有纳摩尔亲和力的基于 1,2,3-三唑的 RGD 肽模拟物通过肟异双功能接头与有效的抗有丝分裂紫杉醇偶联。相对于不表达αvβ3的MCF7细胞，所得构建体保持了与αvβ3整联蛋白的纳摩尔结合浓度，并且在对高度表达αvβ3的U87MG癌细胞的细胞毒性方面显示出11倍的选择性，表明具有良好的癌细胞靶向能力。1 设计 2 逆合成 3 合成 4 固相受体结合试验 5 细胞细胞毒性试验 6 代谢稳定性试验 7 结论