2-(2-nitro-benzylsulfanyl)-ethylamine | 1016891-94-3

• 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: 2-(2-nitro-benzylsulfanyl)-ethylamine
• 英文别名: 2-((2-nitrobenzyl)thio)ethanamine；2-(2-Nitrobenzylthio)ethanamine；2-[(2-nitrophenyl)methylsulfanyl]ethanamine
• CAS: 1016891-94-3
• 化学式: C₉H₁₂N₂O₂S
• 分子量: 212.272
• InChiKey: JCLNAXDNUXWOCC-UHFFFAOYSA-N

物化性质

• 沸点：
  344.6±27.0 °C(Predicted)
• 密度：
  1.261±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  97.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(2-nitro-benzylsulfanyl)-ethylamine 在 sodium carbonate 作用下， 以 乙醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 9.0h， 生成 4-[2-(2-nitrobenzylsulfanyl)ethyl]-3-phenyl-4,5-dihydro-1H-1,2,4-triazole-5-thione
  参考文献：
  名称：

  具有 4-乙基烷基/芳基硫醚取代基的 1,2,4-三唑-3-硫酮化合物是具有再敏化活性的广谱金属-β-内酰胺酶抑制剂

  摘要：

  金属-β-内酰胺酶（MBLs）是革兰氏阴性菌对β-内酰胺类抗生素耐药的重要因素。MBLs 非常令人担忧，因为它们具有碳青霉烯酶活性，它们在主要的人类机会性病原体中迅速传播，而目前还没有临床上有用的抑制剂。在此背景下，我们正在探索基于 1,2,4-triazole-3-thione 支架的化合物作为 MBL 的二锌活性位点的原始配体的潜力，并在其位置 4 和 5 处进行多种取代。在这里，我们提出了一系列在 4 位被含硫醚的烷基链取代的新化合物，该烷基链在其末端具有羧基和/或芳基。几种化合物对K i显示出广谱抑制作用针对 VIM 型酶、NDM-1 和 IMP-1 的 μM 到亚 μM 范围内的值。硫和芳基的存在对于抑制活性很重要，并且通过 X 射线晶体学揭示了 VIM-2 中一些化合物的结合模式。重要的是，体外抗菌药敏试验表明，几种抑制剂能够增强美罗培南对产生 VIM-1 或 VIM-4 的肺

  DOI：

  10.1016/j.ejmech.2021.113873
• 作为产物：
  描述：

  半胱胺盐酸盐 、 2-硝基苄溴 在 lithium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 反应 0.67h， 以67%的产率得到2-(2-nitro-benzylsulfanyl)-ethylamine
  参考文献：
  名称：

  Acrylamide-Based Copolymers Bearing Photoreleasable Thiols for Subsequent Thiol–Ene Functionalization

  摘要：

  A new set of monomers is presented in order to incorporate thiols into radical polymers using a protecting chemistry/photocleavage route. The (co)polymerization kinetics of an o-nitrobenzyl thioether-containing acrylamide derivative are reported. The presence of the o-nitrobenzyl moiety is found to strongly affect the polymerization. Nevertheless, water-soluble copolymers with N,N-dimethylacrylamide (DMAAm) as a comonomer are obtained either by free radical polymerization (10 000 <= M-n <= 17 500 g mol(-1); 1.5 <= PDI <= 1.8) or by reversible addition-fragmentation transfer (RAFT)-mediated controlled/living radical polymerization (2000 <= M-n <= 5700 g mol(-1); 1.1 <= PDI <= 1.2). Deprotection under UV light (lambda = 366 nm) at ambient temperature is followed by UV/vis monitoring of the protecting group release, which proceeds to completion between 40 min and 2 h within the studied range of concentration as demonstrated by H-1 NMR spectroscopy. Thiol-maleimide addition is subsequently carried out and found to proceed with a nearly quantitative yield (ca. 90%) as measured by H-1 NMR. Different block copolymers (9400 <= M-n <= 16 500 g mol(-1); 1.3 <= PDI <= 1.4) with a PDMAAm water-soluble block, a polystyrene hydrophobic block, or a poly(N-isopropylacrylamide) thermosensitive block as the first segment and possessing the photoreleasable thiol moieties in the second block are subsequently synthesized by RAFT-mediated polymerization. We finally demonstrate the orthogonal sequential deprotection and reaction with benzyl maleimide of two different thiol species originating from the thiocarbonylthio functionality and the o-nitrobenzyl protected lateral groups, respectively.

  DOI：

  10.1021/ma202670d

文献信息

• Furan-carboxamide derivatives as novel inhibitors of lethal H5N1 influenza A viruses
  作者：Yongshi Yu、Jie Zheng、Lei Cao、Shu Li、Xiwang Li、Hai-Bing Zhou、Xianjun Liu、Shuwen Wu、Chune Dong

  DOI：10.1039/c7ra00305f

  日期：——

  In this study, we reported the synthesis and biological characterization of a novel series of furan-carboxamide derivatives that were potent inhibitors of the influenza A H5N1 virus. The systematic structure–activity relationship (SAR) studies demonstrated that the 2,5-dimethyl-substituted heterocyclic moiety (furan or thiophene) had significant influence on the anti-influenza activity. In particular

  在这项研究中，我们报道了一系列新型的呋喃甲酰胺衍生物的合成和生物学特性，这些衍生物是甲型H5N1流感病毒的有效抑制剂。系统的结构-活性关系（SAR）研究表明，2,5-二甲基取代的杂环部分（呋喃或噻吩）对抗流感活性具有重要影响。特别地，2，5-二甲基-N-（2-（（（4-硝基苄基）硫代）乙基）-呋喃-3-羧酰胺1a显示出对H5N1病毒的最佳活性，其EC 50值为1.25μM。首次将简单的支架呋喃-羧酰胺衍生物鉴定为致命的H5N1甲型流感病毒的新型抑制剂。
• A new strategy for the synthesis of β-benzylmercaptoethylamine derivatives
  作者：Subrata Ghosh、Gregory P. Tochtrop

  DOI：10.1016/j.tetlet.2009.01.133

  日期：2009.4

  Here, we describe a new experimental approach to the synthesis of the beta-benzylmercaptoethylamine functionality, and illustrate its synthetic utility in multi-component reactions. Although prevalent in modern organic synthesis, no general methods have been described for this functionality. Using a carefully developed LiOH-water-ethanol reaction mixture, we were able to produce a diverse collection of beta-benzylmercaptoethylamines containing a range of sensitive functional groups in excellent yields. To further illustrate their utility in molecular library synthesis, we also report the use of beta-benzylmercaptoethylamines in five different multi-component reactions. (C) 2009 Elsevier Ltd. All rights reserved.
• 1,2,4-Triazole-3-thione compounds with a 4-ethyl alkyl/aryl sulfide substituent are broad-spectrum metallo-β-lactamase inhibitors with re-sensitization activity
  作者：Alice Legru、Federica Verdirosa、Jean-François Hernandez、Giusy Tassone、Filomena Sannio、Manuela Benvenuti、Pierre-Alexis Conde、Guillaume Bossis、Caitlyn A. Thomas、Michael W. Crowder、Melissa Dillenberger、Katja Becker、Cecilia Pozzi、Stefano Mangani、Jean-Denis Docquier、Laurent Gavara

  DOI：10.1016/j.ejmech.2021.113873

  日期：2021.12

  Metallo-β-lactamases (MBLs) are important contributors of Gram-negative bacteria resistance to β-lactam antibiotics. MBLs are highly worrying because of their carbapenemase activity, their rapid spread in major human opportunistic pathogens while no clinically useful inhibitor is available yet. In this context, we are exploring the potential of compounds based on the 1,2,4-triazole-3-thione scaffold

  金属-β-内酰胺酶（MBLs）是革兰氏阴性菌对β-内酰胺类抗生素耐药的重要因素。MBLs 非常令人担忧，因为它们具有碳青霉烯酶活性，它们在主要的人类机会性病原体中迅速传播，而目前还没有临床上有用的抑制剂。在此背景下，我们正在探索基于 1,2,4-triazole-3-thione 支架的化合物作为 MBL 的二锌活性位点的原始配体的潜力，并在其位置 4 和 5 处进行多种取代。在这里，我们提出了一系列在 4 位被含硫醚的烷基链取代的新化合物，该烷基链在其末端具有羧基和/或芳基。几种化合物对K i显示出广谱抑制作用针对 VIM 型酶、NDM-1 和 IMP-1 的 μM 到亚 μM 范围内的值。硫和芳基的存在对于抑制活性很重要，并且通过 X 射线晶体学揭示了 VIM-2 中一些化合物的结合模式。重要的是，体外抗菌药敏试验表明，几种抑制剂能够增强美罗培南对产生 VIM-1 或 VIM-4 的肺
• Acrylamide-Based Copolymers Bearing Photoreleasable Thiols for Subsequent Thiol–Ene Functionalization
  作者：Guillaume Delaittre、Thomas Pauloehrl、Martin Bastmeyer、Christopher Barner-Kowollik

  DOI：10.1021/ma202670d

  日期：2012.2.28

  A new set of monomers is presented in order to incorporate thiols into radical polymers using a protecting chemistry/photocleavage route. The (co)polymerization kinetics of an o-nitrobenzyl thioether-containing acrylamide derivative are reported. The presence of the o-nitrobenzyl moiety is found to strongly affect the polymerization. Nevertheless, water-soluble copolymers with N,N-dimethylacrylamide (DMAAm) as a comonomer are obtained either by free radical polymerization (10 000 <= M-n <= 17 500 g mol(-1); 1.5 <= PDI <= 1.8) or by reversible addition-fragmentation transfer (RAFT)-mediated controlled/living radical polymerization (2000 <= M-n <= 5700 g mol(-1); 1.1 <= PDI <= 1.2). Deprotection under UV light (lambda = 366 nm) at ambient temperature is followed by UV/vis monitoring of the protecting group release, which proceeds to completion between 40 min and 2 h within the studied range of concentration as demonstrated by H-1 NMR spectroscopy. Thiol-maleimide addition is subsequently carried out and found to proceed with a nearly quantitative yield (ca. 90%) as measured by H-1 NMR. Different block copolymers (9400 <= M-n <= 16 500 g mol(-1); 1.3 <= PDI <= 1.4) with a PDMAAm water-soluble block, a polystyrene hydrophobic block, or a poly(N-isopropylacrylamide) thermosensitive block as the first segment and possessing the photoreleasable thiol moieties in the second block are subsequently synthesized by RAFT-mediated polymerization. We finally demonstrate the orthogonal sequential deprotection and reaction with benzyl maleimide of two different thiol species originating from the thiocarbonylthio functionality and the o-nitrobenzyl protected lateral groups, respectively.