sodium ethyl N-hydroxyacetimidate | 120940-23-0

• 分子结构分类: 有机化合物 - 有机盐 - 有机金属盐
• 英文名称: sodium ethyl N-hydroxyacetimidate
• 英文别名: ethyl N-hydroxyacetimidate sodium
• CAS: 120940-23-0
• 化学式: C₄H₈NO₂*Na
• 分子量: 125.103
• InChiKey: XFBUXBYGISYKFX-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -2.06
• 重原子数：
  8.0
• 可旋转键数：
  1.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  44.65
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  甲磺酸正丁酯 、 sodium ethyl N-hydroxyacetimidate 以78%的产率得到ethyl N-butoxyethanimidate
  参考文献：
  名称：

  Novel convenient synthesis of biologically active esters of hydroxylamine

  摘要：

  Alkylation of ethyl N-hydroxyacetimidate with readily available methanesulfonates of functionally substituted alcohols and subsequent deprotection of aminooxy group is a novel and convenient method to prepare functionally substituted esters of hydroxylamine with high overall yield. This approach is a good alternative to well-known reaction of N-hydroxyphthalimide with alcohols under the Mitsunobu conditions. The properties of ethoxyethylidene protection of aminooxy group on the contrary to that of N-alkoxyphthalimide group allow to perform a wide spectra of the transformations in the radical of N-protected hydroxylamine derivatives. This is essential for synthetic strategies consisting in the introduction of N-protected aminooxy group at one of the first steps of synthesis and subsequent transformations of the radical.The inhibitory effect of one of the newly synthesized compound, 1-guanidinooxy-3-aminopropane (GAPA), was compared with that of well-known inhibitors of ornithine decarboxylase namely, alpha-difluoromethylornithine (DFMO) and 1-aminooxy-3-aminopropane (APA) on Leishmania donovani, a protozoan parasite that causes visceral leishmaniasis. GAPA, on the contrary with APA and DFMO, in micromolar concentrations, inhibited the growth of both amastigotes and promastigotes of sodium antimony gluconate-resistant forms of L. donovani.

  DOI：

  10.1007/s00726-009-0410-0
• 作为产物：
  描述：

  乙酰羟肟酸乙酯 在 sodium methylate 作用下， 以 甲醇 为溶剂， 生成 sodium ethyl N-hydroxyacetimidate
  参考文献：
  名称：

  Antiviral efficacy against influenza virus and pharmacokinetic analysis of a novel MEK-inhibitor, ATR-002, in cell culture and in the mouse model

  摘要：

  Antiviral therapies against influenza are required, especially for high-risk patients, severe influenza and in case of highly pathogenic influenza virus (IV) strains. However, currently, licensed drugs that target the virus directly are not very effective and often lead to the development of resistant IV variants. This may be overcome by targeting host cell factors that are required for IV propagation. IV induces a variety of host cell signaling cascades, such as the Raf/MEK/ERK kinase pathway. The activation of this pathway is necessary for IV propagation. MEK-inhibitors block the activation of the pathway on the bottleneck of the signaling cascade leading to impaired virus propagation. In the present study, we aimed to compare the antiviral potency and bioavailability of the MEK-inhibitor CI-1040 versus its major active metabolite ATR-002, in vitro as well as in the mouse model. In cell culture assays, an approximately 10-fold higher concentration of ATR-002 is required to generate the same antiviral activity as for CI-1040. Interestingly, we observed that considerably lower concentrations of ATR-002 were required to achieve a reduction of the viral load in vivo. Pharmacokinetic studies with ATR-002 and CI-1040 in mice have found the C-max and AUC to be far higher for ATR-002 than for CI-1040. Our results thereby demonstrate the in vivo superiorly of the active metabolite ATR-002 over CI-1040 as an antiviral agent despite its weaker cell membrane permeability. Therefore, ATR-002 is an attractive candidate for development as an efficient antiviral agent, especially given the fact that a treatment based on cellular pathway inhibition would be far less likely to lead to viral drug resistance.

  DOI：

  10.1016/j.antiviral.2020.104806

文献信息

• Detection of the PRAME Protein on the Surface of Melanoma Cells Using a Fluorescently Labeled Monoclonal Antibody
  作者：K. A. Sapozhnikova、A. V. Misyurin、N. B. Pestov、E. G. Meleshkina、S. D. Oreshkov、E. P. Ganzhula、A. S. Mikhailova、V. A. Korshun、V. A. Misyurin、V. A. Brylev

  DOI：10.1134/s1068162021050332

  日期：2021.9

  fluorescently labeled monoclonal antibody to the PRAME protein was obtained by periodate oxidation of glycans followed by modification with a bifunctional azido-oxyamine reagent and a “click” reaction with alkyne-modified sulfonated cyanine dye Cy3. A new approach to the synthesis of a bifunctional azido-oxyamine reagent using the ethoxyethylidene protecting group for oxyamine is proposed. The labeled antibodies

  摘要 确定肿瘤标志物 PRAME 蛋白的表达水平对于预测疾病进程和监测抗癌治疗的有效性都很重要。PRAME 蛋白的荧光标记单克隆抗体是通过聚糖的高碘酸盐氧化，然后用双功能叠氮氧胺试剂修饰和与炔烃修饰的磺化花青染料 Cy3 的“点击”反应获得的。提出了一种使用氧胺的乙氧基亚乙基保护基团合成双功能叠氮氧胺试剂的新方法。用紫外/可见吸收光谱表征标记的抗体并确定修饰的化学计量。
• Branched Linkers for Site-Specific Fluorescent Labeling of Antibodies
  作者：Ksenia A. Sapozhnikova、Evgeny L. Gulyak、Vsevolod A. Misyurin、Maria A. Simonova、Ekaterina V. Ryabukhina、Anastasiya V. Alexeeva、Nataliya A. Tikhonova、Natalia A. Lyzhko、Galina P. Popova、Andrey V. Misyurin、Alexey V. Ustinov、Vladimir A. Korshun、Vera A. Alferova、Dmitry Yu. Ryazantsev、Vladimir A. Brylev

  DOI：10.3390/molecules28010425

  日期：——

  methodology for the synthesis of site-specific antibody-dye conjugates with a high degree of labeling. To this end, we synthesized two oxyamine-based branched triazide linkers and coupled them with a periodate-oxidized anti-PRAME antibody 6H8; two oxyamine-based linear monoazide linkers of similar structure were used as controls. The azide-labeled antibodies were subsequently conjugated with fluorescent

  荧光抗体已被证明是分子生物学和诊断学的宝贵工具。它们通常是通过修饰赖氨酸残基而产生的，这会导致高度异质性。因此，如果抗原结合位点受到影响，它们的亲和力可能会受到影响，这种可能性随着标记程度的增加而增加。在这项工作中，我们提出了一种合成具有高度标记的位点特异性抗体-染料偶联物的方法。为此，我们合成了两个基于氧胺的支链三叠氮接头，并将它们与高碘酸氧化的抗 PRAME 抗体 6H8 偶联；两个相似结构的基于羟胺的线性单叠氮化物接头用作对照。叠氮化物标记的抗体随后通过 SPAAC（一种无铜点击反应）与荧光染料结合。与用线性接头制成的对应物相比，支链缀合物具有更高程度的标记。该方法的实用性在通过流式细胞术检测细胞表面的 PRAME 蛋白时得到了证明。
• Synthesis of Steroid Tracers by an Oxime Ligation Method and Their Use in Fluorescent Polarisation Immunoassay
  作者：I. A. Prokhorenko、D. A. Glushchenko、E. L. Gulyak、I. V. Mikhura、V. A. Korshun、L. I. Mukhametova、S. A. Eremin

  DOI：10.1134/s1068162024010060

  日期：2024.2

  fast and reliable method for the quantitative evaluation of steroid hormones is very relevant for scientific and clinical research. The goal of this study was to develop a new universal method for the synthesis of fluorescent tracers from carbonyl-containing biomolecules by oxime ligation. Methods: A method for the synthesis of ketosteroid oxime conjugates with a fluorescein (6-FAM) derivative connected

  摘要 活性：开发一种快速可靠的方法来定量评估类固醇激素对于科学和临床研究非常重要。本研究的目的是开发一种新的通用方法，通过肟连接从含羰基的生物分子合成荧光示踪剂。方法：提出了一种合成酮类固醇肟缀合物的方法，该缀合物具有通过短双功能氨氧基丙基连接体连接的荧光素（6-FAM）衍生物。通过制备型 RP TLC 和 HPLC 分离肟立体异构体。该缀合物用作单克隆抗体荧光偏振免疫测定（FPIA）方法的示踪剂。结果和讨论：研究了示踪剂与单克隆抗体 (mAb) 与黄体酮的结合参数。该示踪剂在测量类固醇激素浓度方面表现出很高的效率，黄体酮的检测限低于先前描述的类似物。发现Z异构体在 FPIA 中比E异构体更敏感。结论：因此，我们开发了一种有效且通用的方法来合成荧光缀合物，其接头长度最适合免疫测定，从而改善了其分析特性并简化了其制备。合成的化合物具有在临床诊断和环境物体分析中实际应用的潜力。